benzyl compounds


Summary: Benzene derivatives that contain a benzyl group with the general formula Phenyl-CH2-R.

Top Publications

  1. Liu Y, Pan S, Peng C, Huang D, Guh J, Chen C, et al. Moscatilin repressed lipopolysaccharide-induced HIF-1alpha accumulation and NF-kappaB activation in murine RAW264.7 cells. Shock. 2010;33:70-5 pubmed publisher
    ..7. Furthermore, the inhibition of moscatilin seemed to be dependent on the repression of HIF-1alpha accumulation and NF-kappaB activation. ..
  2. Paige J, Wu K, Jaffrey S. RNA mimics of green fluorescent protein. Science. 2011;333:642-6 pubmed publisher
    ..Spinach is markedly resistant to photobleaching, and Spinach fusion RNAs can be imaged in living cells. These RNA mimics of GFP provide an approach for genetic encoding of fluorescent RNAs. ..
  3. Chen T, Pan S, Guh J, Liao C, Huang D, Chen C, et al. Moscatilin induces apoptosis in human colorectal cancer cells: a crucial role of c-Jun NH2-terminal protein kinase activation caused by tubulin depolymerization and DNA damage. Clin Cancer Res. 2008;14:4250-8 pubmed publisher
  4. Paige J, Nguyen Duc T, Song W, Jaffrey S. Fluorescence imaging of cellular metabolites with RNA. Science. 2012;335:1194 pubmed publisher
    ..These RNAs constitute a versatile approach for fluorescence imaging of small molecules and have the potential to detect essentially any cellular biomolecule. ..
  5. Schlumpf M, Durrer S, Faass O, Ehnes C, Fuetsch M, Gaille C, et al. Developmental toxicity of UV filters and environmental exposure: a review. Int J Androl. 2008;31:144-51 pubmed publisher
    ..7 mg/kg for 4-MBC and 0.24/0.07 mg/kg for 3-BC. Molecular endpoints were affected by the lowest doses studied. Our data indicate that the potential risk posed by endocrine active UV filters warrants further investigations. ..
  6. Hillard C, Shi L, Tuniki V, Falck J, Campbell W. Studies of anandamide accumulation inhibitors in cerebellar granule neurons: comparison to inhibition of fatty acid amide hydrolase. J Mol Neurosci. 2007;33:18-24 pubmed
  7. Stein U, Greyer H, Hentschel H. Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre. Forensic Sci Int. 2001;118:87-90 pubmed
    ..In one of these cases, a myristicin blood level of 2 microg/ml was measured 8h after ingestion of two to three tablespoonful of nutmeg powder (approx. 14-21 g, or 280-420 mg/kg). ..
  8. Hallstrom H, Thuvander A. Toxicological evaluation of myristicin. Nat Toxins. 1997;5:186-92 pubmed
    ..It is, however, at present not possible to make a complete risk assessment, as studies regarding genotoxicity and chronic toxicity, including reproductive toxicity and carcinogenicity, are still lacking. ..
  9. Søeborg T, Basse L, Halling Sørensen B. Risk assessment of topically applied products. Toxicology. 2007;236:140-8 pubmed

More Information


  1. Beyer J, Ehlers D, Maurer H. Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. Ther Drug Monit. 2006;28:568-75 pubmed
  2. Amarapurkar D, Rane P. Randomised, double-blind, comparative study to evaluate the efficacy and safety of ganaton (itopride hydrochloride) and mosapride citrate in the management of functional dyspepsia. J Indian Med Assoc. 2004;102:735-7, 760 pubmed
    ..7%) (p < 0.05) and poor in 0 (0%) versus 6 (20%) patients respectively. It may be concluded that ganaton (itopride hydrochloride) is superior in efficacy and safety over mosapride citrate in the management of functional dyspepsia. ..
  3. Ho C, Chen C. Moscatilin from the orchid Dendrobrium loddigesii is a potential anticancer agent. Cancer Invest. 2003;21:729-36 pubmed
    ..Thus, the precise nature of its cytotoxic mechanism remains to be determined. Our results in this study imply that moscatilin is potentially efficacious for chemoprevention and/or chemotherapy against some types of cancer. ..
  4. Ortar G, Ligresti A, De Petrocellis L, Morera E, Di Marzo V. Novel selective and metabolically stable inhibitors of anandamide cellular uptake. Biochem Pharmacol. 2003;65:1473-81 pubmed
    ..Unlike other compounds of the same type, OMDM-1, OMDM-2, and OMDM-6 were very stable to enzymatic hydrolysis by rat brain homogenates. ..
  5. Tsubouchi T, Saito T, Mizutani F, Yamauchi T, Iwanaga Y. Stimulatory action of itopride hydrochloride on colonic motor activity in vitro and in vivo. J Pharmacol Exp Ther. 2003;306:787-93 pubmed
    ..Therefore, itopride may be a useful drug for the treatment of functional bowel disorders such as functional constipation. ..
  6. Holtmann G, Talley N, Liebregts T, Adam B, Parow C. A placebo-controlled trial of itopride in functional dyspepsia. N Engl J Med. 2006;354:832-40 pubmed
    ..63 percent, P=0.04). Itopride significantly improves symptoms in patients with functional dyspepsia. ( number, NCT00272103.). ..
  7. Oliva P, Berrino L, De Novellis V, Palazzo E, Marabese I, Siniscalco D, et al. Role of periaqueductal grey prostaglandin receptors in formalin-induced hyperalgesia. Eur J Pharmacol. 2006;530:40-7 pubmed
    ..These data show that periaqueductal grey prostaglandin receptor stimulation increased formalin-induced nociceptive response in the late phase by increasing glutamate release and by producing a biphasic change in GABA release. ..
  8. Łazewska D, Kurczab R, Więcek M, Kaminska K, Satała G, Jastrzebska Wiesek M, et al. The computer-aided discovery of novel family of the 5-HT6 serotonin receptor ligands among derivatives of 4-benzyl-1,3,5-triazine. Eur J Med Chem. 2017;135:117-124 pubmed publisher
    ..SAR-analysis on the basis of both, RBA and docking results, indicated that action on the receptor is related to the hydrophobicity and the size of aromatic moiety substituted by a methylene linker at the position 4 of 1,3,5-triazine. ..
  9. Yu S, Haight A, Kotecki B, Wang L, Lukin K, Hill D. Synthesis of a TRPV1 receptor antagonist. J Org Chem. 2009;74:9539-42 pubmed publisher
    ..A five-step synthesis of a TRPV1 receptor antagonist 1 is described. The key step involves a novel palladium-catalyzed amidation reaction of 4-chloro-1-methylindazole 8 with the benzyl urea 9 to form the unsymmetrically substituted urea 1. ..
  10. Nguyen H, Lavrenov S, Sundar S, Nguyen D, Tseng M, Marconett C, et al. 1-Benzyl-indole-3-carbinol is a novel indole-3-carbinol derivative with significantly enhanced potency of anti-proliferative and anti-estrogenic properties in human breast cancer cells. Chem Biol Interact. 2010;186:255-66 pubmed publisher
  11. Komala I, Ito T, Nagashima F, Yagi Y, Asakawa Y. Cytotoxic bibenzyls, and germacrane- and pinguisane-type sesquiterpenoids from Indonesian, Tahitian and Japanese liverworts. Nat Prod Commun. 2011;6:303-9 pubmed
    ..The structure of each isolated compound was elucidated by using spectroscopic methods and the cytotoxicity was determined by using the WST-8 colorimetric assay. ..
  12. Bird R, Nikolaev A, Pratt D. Microwave and UV excitation spectra of 4-fluorobenzyl alcohol at high resolution. S0 and S1 structures and tunneling motions along the low frequency -CH2OH torsional coordinate in both electronic states. J Phys Chem A. 2011;115:11369-77 pubmed publisher
    ..Possible reasons for these behaviors are discussed. ..
  13. Yu W, Mechawar N, Krantic S, Quirion R. ?7 Nicotinic receptor activation reduces ?-amyloid-induced apoptosis by inhibiting caspase-independent death through phosphatidylinositol 3-kinase signaling. J Neurochem. 2011;119:848-58 pubmed publisher
    ..These findings indicate that the ?7 nAChR activation and PI3K/Akt transduction signaling contribute to the neuroprotective effects of nicotine against A?-induced cell death by modulating caspase-independent death pathways. ..
  14. Vila A, Bugarín M, Mosquera R. Electronic interpretation of conformational preferences in benzyl derivatives and related compounds. J Phys Chem A. 2011;115:13088-95 pubmed publisher
    ..The electron density reorganization can be satisfactorily explained on the basis of these repulsive interactions, while no evidence of larger hyperconjugative delocalization is observed in the preferred conformations. ..
  15. Paul B, Guchhait N. Looking at the Green Fluorescent Protein (GFP) chromophore from a different perspective: a computational insight. Spectrochim Acta A Mol Biomol Spectrosc. 2013;103:295-303 pubmed publisher
    ..Our computations delineate the discernible differences in NLO properties between the neutral and anionic species of HBDI whereby indicating the possibility of development of photoswitchable NLO device. ..
  16. Kamimura A, Kotake T, Ishihara Y, So M, Hayashi T. Kinetic study of the 7-endo selective radical cyclization of N-tert-butyl-o-bromobenzylmethacryl amides: kinetic investigation of the cyclization and 1,7-hydrogen transfer of aromatic radicals. J Org Chem. 2013;78:3961-71 pubmed publisher
    ..Kinetic parameters for hydrogen abstraction from toluene by aryl radicals were also estimated. ..
  17. Jiang H, Yan L, Xu M, Lu W, Cai Y, Wan W, et al. Nucleophile-dependent regioselective reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazolines. J Org Chem. 2013;78:4261-9 pubmed publisher
  18. Llorente R, Llorente Berzal A, Petrosino S, Marco E, Guaza C, Prada C, et al. Gender-dependent cellular and biochemical effects of maternal deprivation on the hippocampus of neonatal rats: a possible role for the endocannabinoid system. Dev Neurobiol. 2008;68:1334-47 pubmed publisher
    ..We provide direct evidence for gender-dependent cellular and biochemical effects of MD on developmental hippocampus, including changes in the endocannabinoid system. ..
  19. Fang Q, Wang F, Zhao H, Liu X, Tu R, Wang D, et al. Strongly coupled excitonic states in H-aggregated single crystalline nanoparticles of 2,5-bis(4-methoxybenzylidene) cyclopentanone. J Phys Chem B. 2008;112:2837-41 pubmed publisher
    ..These results show a perspective that the ability to control the molecular structure and its arrangement in aggregates holds promise for creating novel optical properties in molecular materials. ..
  20. Veldhuyzen van Zanten S. Pitfalls in designing trials of functional dyspepsia: the ascent and demise of itopride. Gut. 2008;57:723-4 pubmed publisher
  21. Wu W, Peng Q, Dong D, Hou X, Wu Y. A dramatic switch of enantioselectivity in asymmetric heck reaction by benzylic substituents of ligands. J Am Chem Soc. 2008;130:9717-25 pubmed publisher
    ..Density functional theory calculations on the reaction mechanism as well as X-ray analysis of 1a-PdCl 2 and 2a-PdCl 2 complexes provide a rational explanation for the above observations. ..
  22. Zhao F, Tan Q, Xiao F, Zhang S, Deng G. Palladium-catalyzed desulfitative cross-coupling reaction of sodium sulfinates with benzyl chlorides. Org Lett. 2013;15:1520-3 pubmed publisher
    ..Various aromatic sodium sulfinates were used as aryl sources via extrusion of SO2 and gave the diarylmethanes in moderate to good yields. ..
  23. Petersen K, Dolan P, Kensler T, Peleg S, Posner G. Low-calcemic, highly antiproliferative, 23-oxa ether analogs of the natural hormone 1 alpha,25-dihydroxyvitamin D3: design, synthesis, and preliminary biological evaluation. J Med Chem. 2007;50:5824-32 pubmed
    ..One of these three 23-oxa analogs has transcriptional potency almost as high as that of calcitriol, even though it binds to the human vitamin D receptor only about 1% as well as calcitriol. ..
  24. Luszczki J, Swiader M, Swiader K, Paruszewski R, Turski W, Czuczwar S. Anticonvulsant and acute adverse effect profiles of picolinic acid 2-fluoro-benzylamide in various experimental seizure models and chimney test in mice. Fundam Clin Pharmacol. 2008;22:69-74 pubmed
    ..p. administration), deserves more attention as a potential antiepileptic drug for status epilepticus patients. ..
  25. Chen Y, Tang L, Feng B, Shi L, Wang H, Wang Y. New bibenzyl glycosides from leaves of Camellia oleifera Abel. with cytotoxic activities. Fitoterapia. 2011;82:481-4 pubmed publisher
    ..All the above 3 bibenzyl glycosides showed cytotoxic activities to Hela and hep2 cell lines. ..
  26. Alves C, Lima L, David J, Lima M, David J, Lima F, et al. In vitro acetylcholinesterase activity of peptide derivatives isolated from two species of Leguminosae. Pharm Biol. 2013;51:936-9 pubmed publisher
    ..Compound 1 is shown to be a potent inhibitor of AChE, with IC50 values similar to the physostigmine control (141.51 µM). ..
  27. Schaffer M, Gröger T, Putz M, Zimmermann R. Forensic profiling of sassafras oils based on comprehensive two-dimensional gas chromatography. Forensic Sci Int. 2013;229:108-15 pubmed publisher
    ..Discrimination of such samples was still possible even in the absence of characteristic main compounds...
  28. Ma J, Yuan L, Ding M, Zhang J, Zhang Q, Xu Q, et al. Determination of itopride hydrochloride in human plasma by RP-HPLC with fluorescence detection and its use in bioequivalence study. Pharmacol Res. 2009;59:189-93 pubmed publisher
    ..89-9.54%. The limit we have used (70-143%) is based on the local regulatory authority (SFDA). The developed method was validated and successfully applied to bioequivalence studies of itopride hydrochloride in healthy male volunteers. ..
  29. Lim H, Lee S, Chen J, Park H. Electrogastrography associated with symptomatic changes after prokinetic drug treatment for functional dyspepsia. World J Gastroenterol. 2012;18:5948-56 pubmed publisher
    ..To evaluate the effect of prokinetic drugs on electrogastrography (EGG) parameters according to symptomatic changes in patients with functional dyspepsia (FD)...
  30. Świąder M, Łuszczki J, Paruszewski R, Świąder K, Turski W. Protective action of nicotinic acid benzylamide in a variety of chemically-induced seizures in mice. Pharmacol Rep. 2016;68:297-300 pubmed publisher
    ..Additionally, Nic-BZA (in dosages of up to 100mg/kg) did not impair long-term memory in mice. Summing up, Nic-BZA has a wide anticonvulsant effect in different experimental epilepsy models. ..
  31. Daud N, Taha R. Plant regeneration and floral bud formation from intact floral parts of African violet (Saintpaulia ionantha H. Wendl.) cultured in vitro. Pak J Biol Sci. 2008;11:1055-8 pubmed
    ..e., stamens or pistils. All sterile or vegetative floral buds and abnormal flowers survived for 3 months in culture but failed to reach anthesis. ..
  32. Prawat U, Chairerk O, Phupornprasert U, Salae A, Tuntiwachwuttikul P. Two new C-benzylated dihydrochalcone derivatives from the leaves of Melodorum siamensis. Planta Med. 2013;79:83-6 pubmed publisher
    ..Compounds 1, 2, and 13 exhibited strong cytotoxicity against human tumor cell lines KB and NCI-H187, with IC50 values in the range of 0.66-7.16 µg/mL. ..
  33. Amiri H. Volatile constituents and antioxidant activity of flowers, stems and leaves of Nasturtium officinale R. Br. Nat Prod Res. 2012;26:109-15 pubmed publisher
    ..In the above tests, methanol extracts of leaves showed higher antioxidant activity than the oils and methanol extracts of stems and flowers...
  34. Harris M, Hanna L, Greene M, Moore C, Jarvo E. Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst. J Am Chem Soc. 2013;135:3303-6 pubmed publisher
    ..Tricyclohexylphosphine ligand provides the product with retention, while an N-heterocyclic carbene ligand provides the product with inversion. ..
  35. Borduas N, Powell D. Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds. J Org Chem. 2008;73:7822-5 pubmed publisher
    ..Kinetic isotope studies support a mechanism involving a benzylic hydrogen abstraction. ..
  36. Naumov P, Kowalik J, Solntsev K, Baldridge A, Moon J, Kranz C, et al. Topochemistry and photomechanical effects in crystals of green fluorescent protein-like chromophores: effects of hydrogen bonding and crystal packing. J Am Chem Soc. 2010;132:5845-57 pubmed publisher
  37. Barnett D, Refaei M, Curley R. Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: synthesis of protected (2S, 3S)-[3-(2)H, (15)N]-tyrosine. J Labelled Comp Radiopharm. 2013;56:6-11 pubmed publisher
    ..Key in the synthesis was the alkylation of (15)N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-?-d chloride. ..
  38. Manoj K, Gonnade R, Bhadbhade M, Shashidhar M. Different interaction motifs of dipolar S=O...C=O contacts that associate diastereomers of 2,4(6)-di-O-benzoyl-6(4)-O-{[(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-ylmethyl]sulfonyl}-myo-inositol 1,3,5-orthoacetate. Acta Crystallogr C. 2007;63:o555-8 pubmed
    ..C=O contacts bridging the former, whereas perpendicular S=O...C=O contacts occur in the latter. The title compound, C(32)H(34)O(11)S, is chiral, owing to the presence of the camphor moiety. ..
  39. Venkatesh V, Kulkarni K. Itopride and pantoprazole outcomes in diabetic gastroparesis trial (IPOD trial). J Indian Med Assoc. 2008;106:814-5 pubmed
    ..There were significant improvement in severity as well as the frequency of all the symptom parameters of the disease (p<0.001). The physicians' evaluation to the therapy was rated either excellent or good. ..
  40. Henrikson J, Hoover A, Joyner P, Cichewicz R. A chemical epigenetics approach for engineering the in situ biosynthesis of a cryptic natural product from Aspergillus niger. Org Biomol Chem. 2009;7:435-8 pubmed publisher
    ..A new fungal metabolite, nygerone A (), featuring a unique 1-phenylpyridin-4(1H)-one core that had previously not been reported from any natural source, has been obtained from Aspergillus niger using a chemical epigenetics methodology. ..
  41. Harper M, Londoño J, Quick K, Londoño J, Flockerzi V, Philipp S, et al. Transient receptor potential channels function as a coincidence signal detector mediating phosphatidylserine exposure. Sci Signal. 2013;6:ra50 pubmed publisher
  42. Abbasi B, Ali J, Ali M, Zia M, Bokhari S, Khan M. Free radical scavenging activity in in vitro-derived tissues of Eruca sativa. Toxicol Ind Health. 2016;32:98-105 pubmed publisher
    ..Investigation of radical scavenging activity showed that callus possesses higher levels of radical scavengers than other plant tissues tested. Phenolics and glucosides are reported to be active components of Eruca sativa phytochemistry. ..
  43. Johansson M, Swart M. Subtle effects control the polymerisation mechanism in ?-diimine iron catalysts. Dalton Trans. 2011;40:8419-28 pubmed publisher
  44. Kimura Y, Sumiyoshi M. Effects of Swertia japonica extract and its main compound swertiamarin on gastric emptying and gastrointestinal motility in mice. Fitoterapia. 2011;82:827-33 pubmed publisher
    ..These findings suggest that the powder and swertiamarin stimulate gastric emptying and gastrointestinal motility by inhibiting the dopamine D(2) receptor. ..
  45. Pilatova M, Varinska L, Perjesi P, Sarissky M, Mirossay L, Solar P, et al. In vitro antiproliferative and antiangiogenic effects of synthetic chalcone analogues. Toxicol In Vitro. 2010;24:1347-55 pubmed publisher
    ..In conclusion, the present study has assessed the in vitro antiproliferative/antiangiogenic potential of chalcone 3. This results generate a rationale for in vivo efficacy studies with this compound in preclinical cancer models. ..
  46. Vera Estrella R, Miranda Vergara M, Barkla B. Zinc tolerance and accumulation in stable cell suspension cultures and in vitro regenerated plants of the emerging model plant Arabidopsis halleri (Brassicaceae). Planta. 2009;229:977-86 pubmed publisher
    ..0 micromoles zinc g(-1) FW, and cell suspension cultures 30.9 micromoles zinc g(-1) DW. Together this work will provide the experimental basis for furthering our knowledge of A. halleri as a model heavy metal hyperaccumulating plant. ..
  47. Avila M, Zougagh M, Escarpa A, Rios A. Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography. J Chromatogr A. 2009;1216:7179-85 pubmed publisher
    ..The precision of the method, expressed as relative standard deviation values, was below 5% in all cases. The applicability of this methodology was tested by analyzing synthetic and real food samples. ..
  48. Fryer R, Muthukumarana A, Harrison P, Nodop Mazurek S, Chen R, Harrington K, et al. The clinically-tested S1P receptor agonists, FTY720 and BAF312, demonstrate subtype-specific bradycardia (S1P?) and hypertension (S1P?) in rat. PLoS ONE. 2012;7:e52985 pubmed publisher
  49. Lanni E, Bosscher M, Ooms B, Shandro C, Ellsworth B, Anderson C. Synthesis of substituted N-benzyl pyridones via an O- to N-alkyl migration. J Org Chem. 2008;73:6425-8 pubmed publisher
    ..This method serves as an efficient means for the preparation of N-benzyl pyridones, quinolones, and pyrimidones. ..
  50. Huang J, Han B, Xu S, Zhou M, Shen W. Heme oxygenase-1 is involved in the cytokinin-induced alleviation of senescence in detached wheat leaves during dark incubation. J Plant Physiol. 2011;168:768-75 pubmed publisher
    ..In contrast, HO-1 inducer hemin could partially mimic the effects of 6-BA. Together, the results suggest that HO-1 might be involved in the CTK-induced alleviation of senescence and lipid peroxidation in detached wheat leaves. ..
  51. Mijovilovich A, Pettersson L, de Groot F, Weckhuysen B. Functional groups and sulfur K-edge XANES spectra: divalent sulfur and disulfides. J Phys Chem A. 2010;114:9523-8 pubmed publisher
    ..It is shown that different ligand groups introduce significant differences in the absorption edge, which poses a problem for the speciation analysis when the ligand groups are not clearly defined. ..
  52. Yang K, Sun L, Liu J, Cui X, Piao H. Synthesis of 2-(4-substituted benzyl-1,4-diazepan-1-yl)-N-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamides and their positive inotropic evaluation. Bioorg Med Chem Lett. 2010;20:4464-7 pubmed publisher
    ..68+/-0.14% increased stroke volume (milrinone 2.38+/-0.05%) at 1 x 10(-5)M in our in vitro study. The chronotropic effects of compounds having significant inotropic effects were also evaluated. ..
  53. Wu D, Mennerich D, Arndt K, Sugiyama K, Ozaki N, Schwarz K, et al. The effects of microsomal prostaglandin E synthase-1 deletion in acute cardiac ischemia in mice. Prostaglandins Leukot Essent Fatty Acids. 2009;81:31-3 pubmed publisher
    ..We conclude that loss of mPGES-1 results in increased PGI(2) formation, and in contrast to inhibition of PGI(2), without worsening acute cardiac ischemic injury. ..