- The brain tissue response to biodegradable poly(methylidene malonate 2.1.2)-based microspheres in the rat
Inserm U646 Ingénierie de la vectorisation particulaire, 10 rue André Bocquel, 49 100 Angers, France
Biomaterials 27:4963-74. 2006
..PMM 2.1.2 was thus shown to be inadequate for intracerebral drug delivery...
- Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular Rauhut-Currier problem
Troy E Reynolds
Department of Chemistry, Northwestern University, Evanston, IL 60208, USA
Org Lett 10:2449-52. 2008
..These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3...
- MATE2 mediates vacuolar sequestration of flavonoid glycosides and glycoside malonates in Medicago truncatula
Plant Biology Division, Samuel Roberts Noble Foundation, Ardmore, Oklahoma 73401, USA
Plant Cell 23:1536-55. 2011
..However, some flavonoid glycoside malonates accumulate to higher levels in MATE2 knockouts than in wild-type controls...
- SmI(2)-mediated carbon-carbon bond fragmentation in alpha-aminomethyl malonates
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xue Yuan Road, Beijing 100083, China
Org Lett 11:4136-8. 2009
A new and efficient samarium diiodide-promoted carbon-carbon bond fragmentation reaction of alpha-aminomethyl malonates, taking place normally at room temperature and generating the corresponding deaminomethylation products in 74-94% ..
- Palladium-catalyzed carbonylation-decarboxylation of diethyl(2-iodoaryl)malonates with imidoyl chlorides: an efficient route to substituted isoquinolin-1(2H)-ones
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada
Org Lett 10:4903-6. 2008
..were synthesized in reasonable to good yields by the palladium-catalyzed cyclization of diethyl(2-iodoaryl)malonates with imidoyl chlorides and carbon monoxide in tetrahydrofuran...
- Sequence of a gene cluster from Klebsiella pneumoniae encoding malonate decarboxylase and expression of the enzyme in Escherichia coli
Mikrobiologisches Institut der Eidgenössischen Technischen Hochschule, Zurich, Switzerland
Eur J Biochem 246:530-8. 1997
..As partial deletion of the mdcR gene impaired growth of the transformants on malonate, MdcR is probably a transcriptional regulator of the mdc genes...
- Effects of cannabinoids in the rat model of Huntington's disease generated by an intrastriatal injection of malonate
URA CEA CNRS 2210, Service Hospitalier Frederic Joliot, DRM, DSV, CEA, 4 Place du General Leclerc, 91401 Orsay Cedex, France
Neuroreport 14:813-6. 2003
- Pd(II)-catalyzed asymmetric addition of malonates to dihydroisoquinolines
IMRAM, Tohoku University, Miyagi 980 8577, Japan
J Am Chem Soc 128:14010-1. 2006
We have developed a highly efficient reaction for catalytic asymmetric addition of malonates to dihydroisoquinolines using chiral Pd(II) complexes...
- Detection and quantification of glycosylated flavonoid malonates in celery, Chinese celery, and celery seed by LC-DAD-ESI/MS
Long Ze Lin
Food Composition Laboratory, Beltsville Human Nutrition Research Center, Agricultural Research Service, U S Department of Agriculture, 103000 Baltimore Avenue, Beltsville, MD 20705, USA
J Agric Food Chem 55:1321-6. 2007
..derivatives was confirmed by their conversion into glycosides upon heating and by comparison of some of the malonates with malonates that had previously been identified in red bell pepper and parsley...
- Nucleocytoplasmic-localized acyltransferases catalyze the malonylation of 7-O-glycosidic (iso)flavones in Medicago truncatula
Xiao Hong Yu
Biology Department, Brookhaven National Laboratory, Upton, NY 11973, USA
Plant J 55:382-96. 2008
..Such C-terminal polypeptide deletion or deletion of the DFGWG motif alone led to improper folding of the transiently expressed GFP fusion protein in living cells, and impaired nuclear localization of the enzyme...
- Inhibitory effects of KAT-681, a liver-selective thyromimetic, on development of hepatocellular proliferative lesions in rats induced by 2-acetylaminofluorene and partial hepatectomy after diethylnitrosamine initiation
Toxicology Laboratories, Research and Development, Kissei Pharmaceutical Co Ltd, 2320 1 Maki, Hotaka, Minamiazumi gun, 399 8305 Nagano, Japan
Arch Toxicol 78:460-6. 2004
..25 mg/kg per day KAT (by 64%). The results of the present study thus suggest that KAT inhibits the development of altered hepatocellular foci and might be a promising chemopreventive agent for hepatocarcinogenesis...
- The thyromimetic T-0681 protects from atherosclerosis
Department of Internal Medicine, Innsbruck Medical University, Innsbruck, Austria
J Lipid Res 50:938-44. 2009
..Our data suggest that liver-selective thyromimetics, such as T-0681, may prove to be useful therapeutic agents against the development of atherosclerosis in humans...
- Enzymic and genetic basis for bacterial growth on malonate
Mikrobiologisches Institut, Eidgenossische Technische Hochschule, ETH Zentrum, Zurich, Switzerland
Mol Microbiol 25:3-10. 1997
..The genetic evidence firmly supports the idea that malonate decarboxylation is carried out by the two different decarboxylases, as deduced from the biochemical studies of the enzymes...
- Malonate metabolism: biochemistry, molecular biology, physiology, and industrial application
Yu Sam Kim
Department of Biochemistry, College of Science, Protein Network Research Center, Yonsei University, Seoul 120 749, Korea
J Biochem Mol Biol 35:443-51. 2002
..In addition to these, the genes matB and matC have been successfully used for generation of the industrial strain of Streptomyces for the production of antibiotics...
- Nephrotoxicity of heptaplatin: a randomized comparison with cisplatin in advanced gastric cancer
Jin Hee Ahn
Section of Hematology Oncology, Department of Internal Medicine, Asan Medical Center, University of Ulsan College of Medicine, Seoul, 138 736, Korea
Cancer Chemother Pharmacol 50:104-10. 2002
..Heptaplatin is a newly developed platinum derivative which has been reported to be less toxic than cisplatin. This study was designed to evaluate the nephrotoxicity of heptaplatin in comparison with that of cisplatin...
- Characterization of novel astragaloside malonates from Radix Astragali by HPLC with ESI quadrupole TOF MS
Key Laboratory of Modern Chinese Medicines China Pharmaceutical University, Ministry of Education, Nanjing, P R China
J Sep Sci 33:570-81. 2010
..With the strategy of target precursor ions scan, a total of 22 astragalosides including 8 astragaloside malonates were screened and characterized from the methanolic extract of Radix Astragali by HPLC-Q-TOF/MS...
- Adenosinergic protection of dopaminergic and GABAergic neurons against mitochondrial inhibition through receptors located in the substantia nigra and striatum, respectively
Peter D Alfinito
Levine Neuroscience Laboratory, Department of Neurology, University of Medicine and Dentistry of New Jersey Robert Wood Johnson Medical School, Piscataway, New Jersey 08854, USA
J Neurosci 23:10982-7. 2003
..Interestingly, these effects are mediated by A1 and A2a receptors located in the substantia nigra for DAergic neurons and in the striatum for GABAergic neurons...
- Mitochondrial toxin inhibition of [(3)H]dopamine uptake into rat striatal synaptosomes
William F Maragos
Department of Neurology, Kentucky Clinic, Room L 445, University of Kentucky Medical Center, Lexington, KY 40536, USA
Biochem Pharmacol 63:1499-505. 2002
..e. noncompetitive inhibition of the DAT...
- Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis. Part II. Scope and applications
B M Trost
Department of Chemistry, Stanford University, Stanford, CA 94305, USA
J Am Chem Soc 123:3687-96. 2001
..In conjunction with the subsequent reactions that occur with high stereospecificity, allylic gem-dicarboxylates serve as synthons for a double allylic transformation...
- Striatal damage and oxidative stress induced by the mitochondrial toxin malonate are reduced in clorgyline-treated rats and MAO-A deficient mice
William F Maragos
University of Kentucky, Department of Neurology, USA
Neurochem Res 29:741-6. 2004
..These findings indicate that normal levels of MAO-A participate in expression of malonate toxicity by a mechanism involving oxidative stress...
- Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate
W L Nixdorf
Program in Basic and Clinical Neuroscience, Department of Psychiatry, Case Western Reserve University, Cleveland, USA
J Neurochem 77:647-54. 2001
..Overall, these results highlight the importance of energy balance to the function of DA and 5-HT neurons and to the toxic effects of MDMA...
- Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance
Séamus H McCooey
Centre for Synthesis and Chemical Biology, Department of Chemistry, Trinity College, University of Dublin, Dublin 2, Ireland
Angew Chem Int Ed Engl 44:6367-70. 2005
- Mitochondrial stress-induced dopamine efflux and neuronal damage by malonate involves the dopamine transporter
Lily Y Moy
Department of Neurology, University of Medicine and Dentistry of New Jersey, Robert Wood Johnson Medical School, Piscataway, NJ 08854, USA
J Pharmacol Exp Ther 320:747-56. 2007
- Mechanisms of the interaction of nitroxyl with mitochondria
Department of Pathology, University of Alabama at Birmingham, Birmingham, AL 35294, USA
Biochem J 379:359-66. 2004
- Organocatalytic conjugate addition of malonates to alpha,beta-unsaturated aldehydes: asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
The Danish National Research Foundation Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark
Angew Chem Int Ed Engl 45:4305-9. 2006
- Catalytic asymmetric Michael reactions with enamides as nucleophiles
Graduate School of Pharmaceutical Sciences and Department of Chemistry, School of Science, The University of Tokyo, The HFRE Division, ERATO, JST, Hongo, Bunkyo ku, Tokyo 113 0033, Japan
Angew Chem Int Ed Engl 46:7803-5. 2007
- Ternary phase diagram for the Belousov-Zhabotinsky reaction-induced mechanical oscillation of intelligent PNIPAM colloids
Artie McFerrin Department of Chemical Engineering, Texas A and M University, College Station, Texas 77843, USA
J Phys Chem A 111:12081-5. 2007
- Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation
Organisch Chemisches Institut der Universitat Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Angew Chem Int Ed Engl 45:2466-9. 2006
- Practical synthesis of optically active alpha,alpha-disubstituted malonamic acids through asymmetric hydrolysis of malonamide derivatives with Rhodococcus sp. CGMCC 0497
Zhong Liu Wu
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
J Org Chem 68:2479-82. 2003
..The enantioselectivity originated from the effects of a highly enantioselective amidase. The products could be converted to valuable (R)- or (S)-alpha,alpha-dialkylated amino acids after routine conversions...
- Strontium-catalyzed highly enantioselective Michael additions of malonates to enones
Department of Chemistry, School of Science, The University of Tokyo, The HFRE Division, ERATO, JST, Hongo, Bunkyo ku, Tokyo 113 0033, Japan
J Am Chem Soc 130:2430-1. 2008
- A general organocatalytic enantioselective malonate addition to alpha,beta-unsaturated enones
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
Chemistry 14:6155-65. 2008
A general enantioselective organocatalytic conjugate addition procedure of a variety of malonates to alpha,beta-unsaturated enone systems is presented. The reaction is efficiently catalysed by the pyrrolidinyl tetrazole catalyst 1...
- Desymmetrization-like catalytic enantioselective fluorination of malonates and its application to pharmaceutically attractive molecules
Dhande Sudhakar Reddy
Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa Ku, Nagoya 466 8555, Japan
Angew Chem Int Ed Engl 47:164-8. 2008
- Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine
Peter S Hynes
School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom
Org Lett 10:1389-91. 2008
- Manganese(III)-catalyzed free radical reactions on trimetallic nitride endohedral metallofullerenes
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24060 0212, USA
J Am Chem Soc 129:15710-7. 2007
..These are the highest levels of substitution of TNT metallofullerenes reported so far...
- Neurodegeneration in methylmalonic aciduria involves inhibition of complex II and the tricarboxylic acid cycle, and synergistically acting excitotoxicity
Jürgen G Okun
Department of Pediatrics, Division of Metabolic and Endocrine Diseases, Im Neuenheimer Feld 150, Federal Republic of Germany
J Biol Chem 277:14674-80. 2002
..We propose that neuropathogenesis of methylmalonic aciduria may involve an inhibition of complex II and the tricarboxylic acid cycle by accumulating toxic organic acids, and synergistic secondary excitotoxic mechanisms...
- N-Acetylaspartate, a marker of both cellular dysfunction and neuronal loss: its relevance to studies of acute brain injury
, Laboratoire de Pharmacodynamie, , Dijon, France Service de Neurologie, Centre Hospitalier Universitaire, Dijon, France
J Neurochem 77:408-15. 2001
..Overall results show that cellular dysfunction can cause higher reductions in NAA level than neuronal loss, thus making of NAA quantification a potential tool for visualizing the penumbra area in stroke patients...
- Spectrophotometric study of fluorescence sensing and selective binding of biochemical substrates by 2,2'-bridged bis(beta-cyclodextrin) and its water-soluble fullerene conjugate
Department of Chemistry, State Key Laboratory of Elemento organic Chemistry, Nankai University, Tianjin 300071, P R China
J Phys Chem B 109:23739-44. 2005
- Lack of evidence of direct mitochondrial involvement in the neuroprotective effect of minocycline
Ipsen Institut Henri Beaufour, 5 Avenue du Canada, 91966 Les Ulis, France
Eur J Pharmacol 505:111-9. 2004
..From these experiments, the neuroprotective activity of minocycline appears more related to its antiinflammatory activity than to a direct beneficial action on mitochondria...
- Protection of malonate-induced GABA but not dopamine loss by GABA transporter blockade in rat striatum
Gail D Zeevalk
Department of Neurology, University of Medicine and Dentistry of New Jersey, Piscataway, New Jersey 08854, USA
Exp Neurol 176:193-202. 2002
..These findings also point to fundamental differences between immature and adult neurons in the downstream involvement of GABA receptors during metabolic insult...
- A novel systemically active caspase inhibitor attenuates the toxicities of MPTP, malonate, and 3NP in vivo
Department of Neurology and Neuroscience, Weill Medical College of Cornell University, New York, NY 10021, USA
Neurobiol Dis 17:250-9. 2004
..These findings suggest that systematically active broad-spectrum caspase inhibitors maybe useful in the treatment of neurodegenerative diseases such as PD and HD...
- Role of corticostriatal and nigrostriatal inputs in malonate-induced striatal toxicity
Centre for Brain Repair, Cambridge University, UK
Neuroreport 12:89-93. 2001
..These data suggest that malonate-induced toxicity in the striatum depends upon the integrity of interactive influences from both glutamatergic and dopaminergic afferents...
- In vivo quantification of localized neuronal activation and inhibition in the rat brain using a dedicated high temporal-resolution beta +-sensitive microprobe
Institut de Physique Nucleaire, Interface Physique Biologie, 91406 Orsay, France
Proc Natl Acad Sci U S A 99:10807-12. 2002
- Neuroprotective effects mediated by dopamine receptor agonists against malonate-induced lesion in the rat striatum
Laboratory of Functional Neurochemistry, IRCCS C Mondino, Pavia, Italy
Neurol Sci 24:180-1. 2003
..Our data suggest that malonate- induced striatal toxicity can be attenuated by systemic administration of dopamine agonists, with D1 and D2 agonists showing different profiles of efficacy...
- Time course of oxidative stress, lesion and edema after intrastriatal injection of malonate in rat: effect of alpha-phenyl-N-tert-butylnitrone
Laboratoire de Pharmacologie, UPRES EA2510, Universite Rene Descartes, 4 avenue de l Observatoire, 75006 Paris, France
Fundam Clin Pharmacol 19:57-64. 2005
..Taken together, these results show that malonate induced a severe oxidative stress leading to the rapid development of the lesion. PBN demonstrates anti-edematous properties that are not sufficient to reduce the lesion...
- Biphasic modulation by nitric oxide of caspase activation due to malonate injection in rat striatum
Laboratoire de Pharmacologie, Universite Rene Descartes, 4 avenue de l Observatoire, 75006 Paris, France
Eur J Pharmacol 483:259-65. 2004
..Thus NO production by the neuronal isoform of NO-synthase is not the major event leading to caspase activation due to malonate. However, NO seems to have pro- and anti-caspase effects that neutralize each other...
- Dopamine receptor agonists mediate neuroprotection in malonate-induced striatal lesion in the rat
Marie Therese Armentero
Laboratory of Functional Neurochemistry, IRCCS, C Mondino, Pavia, Italy
Exp Neurol 178:301-5. 2002
..Our data suggest that malonate-induced striatal toxicity can be attenuated by systemic administration of dopamine agonists, with D(1) and D(2) agonists showing different profiles of efficacy...
- Mitochondrial permeability transition in neuronal damage promoted by Ca2+ and respiratory chain complex II inhibition
Evelise N Maciel
Departamento de Patologia Clinica, Faculdade de Ciencias Medicas, Universidade Estadual de Campinas, Campinas, Brazil
J Neurochem 90:1025-35. 2004
..We propose that under conditions in which mitochondrial complex II is partially inhibited in the CNS, neuronal cell death involves the induction of PT...
- Methylmalonate inhibits succinate-supported oxygen consumption by interfering with mitochondrial succinate uptake
S R Mirandola
Departamento de Patologia Clinica, Faculdade de Ciencias Medicas, Universidade Estadual de Campinas, Campinas, SP 13083 887, Brazil
J Inherit Metab Dis 31:44-54. 2008
- Effect of oxygen on activation state of complex I and lack of oxaloacetate inhibition of complex II in Langendorff perfused rat heart
Molecular Biology Division, VA Medical Center, 4150 Clement Street, San Francisco, CA 94121, USA
FEBS Lett 556:64-8. 2004
..In addition, these studies show that complex II is fully active in the mitochondrion and not inhibited by OAA regardless of the oxygen concentration...
- The endogenous mitochondrial complex II inhibitor malonate regulates mitochondrial ATP-sensitive potassium channels: implications for ischemic preconditioning
Andrew P Wojtovich
Department of Pharmacology and Physiology, University of Rochester Medical Center, Rochester, NY 14642, USA
Biochim Biophys Acta 1777:882-9. 2008
..Together, these observations suggest that complex II inhibition by endogenously formed malonate may represent an important activation pathway for mK(ATP) channels during IPC...
- Cooperative interaction between ascorbate and glutathione during mitochondrial impairment in mesencephalic cultures
Department of Neurology, University of Medicine and Dentistry of New Jersey, Robert Wood Johnson Medical School, Piscataway, New Jersey, USA
J Neurochem 86:1487-97. 2003
..It is speculated that these events are linked by glutaredoxin, an enzyme shown to contain both dehydroascorbate reductase as well as glutathione thioltransferase activities...
- Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis. Part I. Asymmetric addition of malonate nucleophiles
B M Trost
Department of Chemistry, Stanford University, Stanford, California 94305, USA
J Am Chem Soc 123:3671-86. 2001
Asymmetric alkylations of allylic geminal dicarboxylates with dialkyl malonates have been investigated...
- 3-Aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase inhibitors
Department of Chemistry, Merck Research Laboratories, Boston, MA 02115, USA
Bioorg Med Chem Lett 16:4620-3. 2006
..Starting from a derivative with an IC(50) = 1.4 microM, SAR studies led to compounds with more than 70-fold increase in potency (IC(50) < 20 nM)...
- Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands
Neil A Beare
Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
J Org Chem 67:541-55. 2002
..reactions of aryl bromides and chlorides with two common stabilized carbanions-enolates of dialkyl malonates and alkyl cyanoesters-are reported...
- Catalytic relationships between type I and type II iterative polyketide synthases: The Aspergillus parasiticus norsolorinic acid synthase
School of Chemistry, University of Bristol, Cantock s Close, Clifton, Bristol, BS8 1TS, UK
Chembiochem 7:1951-8. 2006
..The NSAS holo-ACP was also active in actinorhodin minimal PKS assays, but only in the presence of exogenous malonyl transferases...
- Improved reagent for electrophilic amination of stabilized carbanions
Jason A Smulik
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA
Org Lett 5:4187-90. 2003
..Reagent 2 reacts efficiently with stabilized sodium or potassium enolates derived from malonates, phenylacetates, and phenylacetonitriles and is sufficiently soluble for use in solution at -78 degrees C.
- The decarboxylative Blaise reaction
Jae Hoon Lee
Chemical Development Division, LG Life Sciences, Ltd R and D, 104 1 Moonji dong, Yusong gu, Daejeon 305 380, Korea
J Org Chem 72:10261-3. 2007
..Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lacrimatory reagent, and is possible with 0.5-1.0 equiv of zinc chloride...
- Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals
Dennis P Curran
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
J Org Chem 68:2972-4. 2003
Reduction of allyl 2-iodobenzyl malonates with triphenyltin hydrides generates aryl radicals that partition between 6-exo cyclization, 7-endo cyclization, and 1,5-hydrogen atom transfer...
- Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: a one-pot synthesis of methylenetetrahydrofurans
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo ku, Tokyo 113 0033, Japan
Org Lett 6:2015-7. 2004
..In the presence of catalytic amounts of zinc triflate [Zn(OTf)(2)] and triethylamine (Et(3)N), various 2-alkylidene-1,3-dicarbonyl compounds reacted with propargyl alcohol to give 3- or 4-methylene tetrahydrofurans in excellent yields...
- Boc-protected amines via a mild and efficient one-pot Curtius rearrangement
Departement de Chimie, Universite de Montreal, P O Box 6128, Station Downtown, Montreal, Quebec, Canada H3C 3J7
Org Lett 7:4107-10. 2005
..These reaction conditions are compatible with a variety of substrates, including malonate derivatives, which provide access to protected amino acids...
- Synthesis of indenes by the transition metal-mediated carboannulation of alkynes
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA
J Org Chem 72:251-62. 2007
..The third method involves intermolecular palladium-catalyzed arylation of the arylalkynes formed in the first step of the second method...
- ESI-MS studies on the mechanism of Pd0-catalyzed three-component tandem double addition-cyclization reaction
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P R China
J Am Chem Soc 127:13060-4. 2005
..characterized by the high-resolution ESI-FTMS technology, on the basis of which a mechanism was proposed for the Pd0-catalyzed three-component tandem double addition cyclization of organic halides, 2-(2,3-allenyl)malonates, and imines.
- Conformations, energies, and intramolecular hydrogen bonds in dicarboxylic acids: implications for the design of synthetic dicarboxylic acid receptors
Thanh Ha Nguyen
Faculty of Pharmacy, University of Sydney, NSW 2006, Australia
J Comput Chem 26:1233-41. 2005
..Intramolecular H-bond redshifts of 170-250 cm(-1) have been estimated from the results of the harmonic frequency analyses...
- A convenient method for the efficient removal of ruthenium byproducts generated during olefin metathesis reactions
Y M Ahn
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66044, USA
Org Lett 3:1411-3. 2001
..Treatment of the crude reaction products with triphenylphosphine oxide or dimethyl sulfoxide, followed by filtration through silica gel, was found to be a practical and effective method to remove colored ruthenium byproducts...
- Efficient removal of ruthenium byproducts from olefin metathesis products by simple aqueous extraction
Soon Hyeok Hong
The Arnold and Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA
Org Lett 9:1955-7. 2007
..Simple aqueous extraction removed ruthenium byproducts efficiently from ring-closing metathesis (RCM) reactions catalyzed by a poly(ethylene glycol) (PEG) supported N-heterocyclic carbene-based ruthenium complex...
- Novel autoxidation and Michael addition of a butenolide-containing sugar leading to a C-branched-chain glucopyranosidulose, and X-ray structure of intermediates
Hong Min Liu
Department of Chemistry, Zhengzhou University, Daxue Road, Zhengzhou 450052, PR China
Carbohydr Res 338:1737-43. 2003
..The autoxidations are also performed in weakly basic, neutral and weakly acidic medium, respectively...
- Michael addition of ortho-lithiated aryloxiranes to alpha,beta-unsaturated malonates: synthesis of tetrahydroindenofuranones
Dipartimento Farmaco Chimico, Universita di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi, Via E Orabona 4, I 70125 Bari, Italy
Org Lett 10:1947-50. 2008
..of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described...
- Convenient syntheses and transformations of 2-C-malonyl carbohydrates
Department of Chemistry, University of Potsdam, Karl Liebknecht Strasse 24 25, 14476 Potsdam, Germany
Chemistry 13:10152-67. 2007
2-C-malonyl carbohydrates were synthesized in only few steps and high yields by radical additions of malonates to glycals...
- Regioselective tandem dimethylsulfonium methylide addition-eliminative olefination of diendioates: a novel route to 1,3-butadien-2-ylmalonates
Bio Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India
Org Lett 9:5071-4. 2007
- Enantioselective syntheses of tremulenediol A and tremulenolide A
Brandon L Ashfeld
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA
Org Lett 7:4535-7. 2005
..This strategy was applied to the first enantioselective syntheses of tremulenediol A and tremulenolide A...
- Preparation of pyrrolidine-based PDE4 inhibitors via enantioselective conjugate addition of alpha-substituted malonates to aromatic nitroalkenes
Paul J Nichols
Department of Process Chemistry Research, Array BioPharma, 3200 Walnut Street, Boulder, Colorado 80301, USA
Org Lett 8:1495-8. 2006
reaction: see text] The enantioselective conjugate addition of alpha-substituted malonates to aromatic nitroalkenes generates a stereocenter at the carbon bearing the aromatic group and an adjacent prochiral center from the alpha-..
- A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core
Paul R Blakemore
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331 4003, USA
Org Lett 7:4721-4. 2005
..Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to alpha-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography...
- gem-Dibromomethylarenes: a convenient substitute for noncommercial aldehydes in the knoevenagel-doebner reaction for the synthesis of alpha,beta-unsaturated carboxylic acids
John Kallikat Augustine
Syngene International Ltd, Biocon Park, Plot Nos 2 and 3, Bommasandra IV Phase, Jigani Link Road, Bangalore 560 100, India
J Org Chem 72:9854-6. 2007
..gem-Dibromomethylarenes are employed for the first time in the Knoevenagel-Doebner reaction as aldehyde equivalents for the efficient synthesis of alpha,beta-unsaturated carboxylic acids...
- LC/UV/ESI-MS analysis of isoflavones in Edamame and Tofu soybeans
New Use Agriculture and Natural Plant Products Program, Department of Plant Biology and Pathology, Cook College, Rutgers University, 59 Dudley Road, New Brunswick, New Jersey, USA
J Agric Food Chem 52:2763-9. 2004
..a total 16 isoflavones, including three aglycones, three glycosides, two glycoside acetates, and eight glycoside malonates. The major isoflavones in soybean seeds were daidzein and genistein glycoside and their malonate conjugates...
- Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection
New Use Agriculture and Natural Plant Products Program, Department of Plant Biology and Pathology, Cook College, Rutgers University, 59 Dudley Road, New Brunswick, NJ 08901, USA
J Chromatogr A 1016:195-209. 2003
..The separated isoflavones including aglycones, glycosides and glycoside malonates, were individually analyzed and identified by their molecular ions and characteristic fragment ion peaks using ..
- Flavonoids in Leguminosae: analysis of extracts of T. pratense L., T. dubium L., T. repens L., and L. corniculatus L. leaves using liquid chromatography with UV, mass spectrometric and fluorescence detection
Eva de Rijke
Department of Analytical Chemistry and Applied Spectroscopy, Free University, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
Anal Bioanal Chem 378:995-1006. 2004
..In T. pratense and T. repens, the main constituents were flavonoid glucoside-(di)malonates, while T. dubium and L. corniculatus mainly contained flavonoid (di)glycosides...
- Variation in the composition of the essential oils, phenolic compounds and mineral elements of Hypericum perforatum L. growing in Estonia
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Nat Prod Res 25:496-510. 2011
..to the earlier published polyphenols, several new phenolic acids and flavonoids, such as quercetin hexoside malonates and an A-type catechin-epicatechin trimer were identified in this Hypericum for the first time...
- Phosphoramidites are efficient, green organocatalysts for the Michael reaction. Mechanistic insights into the phosphorus-catalyzed Michael reaction of alkynones and implications for asymmetric catalysis
Robert B Grossman
Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506 0055, USA
J Org Chem 68:871-4. 2003
..phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, alpha-cyano esters, beta-keto esters, and nitro compounds...
- LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)
L Z Lin
Research Laboratory of Natural Products Chemistry, A M Todd Botanicals, Eugene, Oregon 97402, USA
J Agric Food Chem 48:354-65. 2000
..ionization-mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense)...
- Phenolic compounds and chromatographic profiles of pear skins (Pyrus spp.)
Long Ze Lin
Food Composition and Methods Development Laboratory, Beltsville Human Nutrition Research Center, Agricultural Research Service, U S Department of Agriculture, Beltsville, Maryland 20705 3000, USA
J Agric Food Chem 56:9094-101. 2008
..Peckham, Red, Red D'Anjou, and Seckel) contained significant quantities of isorhamnetin glycosides and their malonates and lesser quantities of quercetin glycosides...
- Catalytic asymmetric ring-opening of meso-aziridines with malonates under heterodinuclear rare earth metal Schiff base catalysis
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo ku, Tokyo 113 0033, Japan
J Am Chem Soc 133:5791-3. 2011
Catalytic asymmetric ring-opening of meso-aziridines with malonates is described. The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction...
- Enantioselective Friedel-Crafts alkylation of indoles with trifluoroethylidene malonates by copper-bis(oxazoline) complexes: construction of trifluoromethyl-substituted stereogenic tertiary carbon center
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Rd, Shanghai, 200032, China
J Org Chem 76:2282-5. 2011
An enantioselective alkylation of indoles with trifluoroethylidene malonates catalyzed by copper(II)-bis (oxazoline) complexes has been developed...
- Mechanistic studies on the catalytic asymmetric Mannich-type reaction with dihydroisoquinolines and development of oxidative Mannich-type reactions starting from tetrahydroisoquinolines
Synthetic Organic Chemistry Laboratory, RIKEN 2 1 Hirosawa, Wako, Saitama 351 0198, Japan
J Org Chem 73:5859-71. 2008
Detailed mechanistic studies on our recently reported asymmetric addition reactions of malonates to dihydroisoquinolines (DHIQs) catalyzed by chiral Pd(II) complexes were carried out...
- Enantioselective and regioselective organocatalytic conjugate addition of malonates to nitroenynes
Xiao Jiao Li
Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 China
Chem Asian J 6:220-5. 2011
..Notably, the protocol worked well with both aryl- and alkyl-substituted alkynyl substrates...
- Synthesis of Dibenz[b,f]oxepins via Manganese(III)-Based Oxidative 1,2-Radical Rearrangement
Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2 39 1, Kumamoto 860 8555, Japan
J Org Chem 74:3978-81. 2009
The oxidation of monoalkyl 2-(9H-xanthenyl)malonates 1 with Mn(OAc)(3) gave the 9- or 10-dibenz[b,f]oxepincarboxylates 2 in good yields...
- Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-h oxaziridines derived from camphor and fenchone
Philip C Bulman Page
Department of Chemistry, Loughborough University, Leicestershire LE11 3TU, England
J Org Chem 67:7787-96. 2002
..Nitrogen is transferred, together with the camphor/fenchone unit, when deprotonated esters, malonates, and nitriles are used as nucleophiles...
- Lewis Base-Promoted Hydrosilylation of Cyclic Malonates: Synthesis of beta-Substituted Aldehydes and gamma-Substituted Amines
Christopher G Frost
Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom
J Org Chem 74:3599-602. 2009
The Lewis base-promoted hydrosilylation of cyclic malonates provides a convenient synthesis of beta-substituted aldehydes...
- High-performance liquid chromatography (HPLC) analysis of phenolic compounds in berries with diode array and electrospray ionization mass spectrometric (MS) detection: ribes species
Kaisu R Määttä
Institute of Applied Biotechnology and Food and Health Research Centre, University of Kuopio, PO Box 1627, FIN 70211 Kuopio, Finland
J Agric Food Chem 51:6736-44. 2003
..However, cyanidin 3-O-sambubioside and quercetin hexoside-malonate were notable phenolic compounds in red currant. Flavonol hexoside-malonates were identified and quantified in the berries of currants for the first time.
- Ytterbium-catalyzed conjugate allylation of alkylidene malonates
EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King s Buildings, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom
J Org Chem 76:4112-8. 2011
Alkylidene malonates undergo efficient conjugate allylation upon treatment with allylstannanes or allylsilanes under the action of ytterbium catalysis.
- Stereoselective synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates by tandem oxidative cyclization and neighboring group-assisted decarboxylation
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China
J Org Chem 75:6994-7. 2010
..neighboring group-assisted decarboxylation of the Michael adducts of 2-cyanoacetamides with α,β-unsaturated malonates. This method affords the desired highly functionalized cyclopropanes in moderate to good yields and with ..
- Synthesis of new C2- symmetric fluoren-9-ylidene malonate derived bis(oxazoline) ligands and their application in Friedel-Crafts reactions
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
Molecules 15:8582-92. 2010
..Their asymmetric catalytic properties in the Friedel-Crafts reactions of indoles with arylidene malonates were evaluated, and the Cu(OTf)2 complex of a fluoren-9-ylidene malonate-derived bis(oxazoline) bearing a phenyl ..
- A new reactivity pattern for vinyl bromides: cine-substitution via palladium catalysed C-N coupling/Michael addition reactions
Michael C Willis
Department of Chemistry, University of Bath, Bath BA2 7AY, UK
Org Biomol Chem 3:3094-5. 2005
..can be used to convert vinyl bromides to the corresponding enamines, which are reacted in situ with alkylidene malonates to provide Michael adducts. The overall transformation results in cine-substitution of the starting vinyl bromide...
- Development of microwave assisted extraction for the simultaneous determination of isoflavonoids and saponins in radix astragali by high performance liquid chromatography
Jing Zheng Song
Chinese Medicine Laboratory, Hong Kong Jockey Club Institute of Chinese Medicine, Shatin, Hong Kong, China
J Sep Sci 30:819-24. 2007
..It was found that flavonoid glycoside malonates were converted into their related glycosides during the prolonged conventional extraction, thus affecting the ..
- Highly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization
Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Seoul 151 742, Korea
J Am Chem Soc 133:4924-9. 2011
A novel enantioselective synthetic method for the construction of a quaternary carbon center from malonates via phase-transfer catalytic (PTC) alkylation has been developed...
- Water-compatible iminium activation: highly enantioselective organocatalytic Michael addition of malonates to α,β-unsaturated enones
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000 China
J Org Chem 75:7428-30. 2010
The highly enantioselective Michael addition of malonates to α,β-unsaturated ketones in water was reported to be catalyzed by a primary-secondary diamine catalyst containing a long alkyl chain...
- Hydrogen bond directed highly regioselective palladium-catalyzed allylic substitution
Gregory R Cook
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105 5516, USA
J Am Chem Soc 125:5115-20. 2003
..to be directed to the internal carbon (branched:linear, 75:25 to >98:2), whereas sulfonamides, amines, and malonates added only to the terminal carbon of the allyl complex...
- Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates
Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China
Bioorg Med Chem Lett 21:3381-3. 2011
..were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature...
- Enantioselective organocatalytic Michael addition of aldehydes to trifluoroethylidene malonates
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PRC
Org Lett 12:4655-7. 2010
..highly enantioselective, organocatalytic Michael addition reaction of aldehydes with trifluoroethylidene malonates is described...
- Palladium-catalyzed cyclocarbonylation-decarboxylation of diethyl(2-iodoaryl)malonates with vinyl ketones affording functionalized enolic 2-acyl-3,4-dihydronaphthalenones
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada
Org Lett 11:3278-81. 2009
..moderate to excellent yields by the palladium-catalyzed cyclocarbonylation-decarboxylation of diethyl(2-iodoaryl)malonates with vinyl ketones and carbon monoxide...
- Highly enantioselective Michael addition of malonates to beta,gamma-unsaturated alpha-ketoesters catalyzed by chiral N,N'-dioxide-Yttrium(III) complexes with convenient procedure
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China
Chem Commun (Camb) 46:3601-3. 2010
Highly enantioselective Michael addition of malonates to beta,gamma-unsaturated alpha-ketoesters has been promoted by chiral N,N'-dioxide-Yttrium(iii) complexes, providing the corresponding products in excellent yields with 94-99% ee ..
- Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones
Stephen G Davies
Department of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
Org Biomol Chem 5:1405-15. 2007
..Asymmetric three-component couplings of alpha,beta-unsaturated esters and alkylidene malonates initiated by lithium amide conjugate addition proceeds with high levels of 2,3-anti stereoselectivity, with ..