bridged ring heterocyclic compounds
Summary: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms.
- Solé D, Urbaneja X, Bonjoch J. Synthesis of the 4-azatricyclo[184.108.40.206(4,8)]undecan-10-one core of daphniphyllum alkaloid calyciphylline A using a Pd-catalyzed enolate alkenylation. Org Lett. 2005;7:5461-4 pubmed
- Yamazaki S, Morikawa S, Miyazaki K, Takebayashi M, Yamamoto Y, Morimoto T, et al. Zinc-catalyzed reactions of ethenetricarboxylates with 2-(trimethylsilylethynyl)anilines leading to bridged quinoline derivatives. Org Lett. 2009;11:2796-9 pubmed publisher..The reaction of 1b with 2'-aminoacetophenone also gave the bridged quinoline derivative in 41% yield. Thermal reaction of bridged quinolines (180-190 degrees C) afforded indole derivatives in moderate to good yields. ..
- Pearson W, Mans D, Kampf J. Cycloadditions of 2-azaallyllithium species with conjugated polyenes. J Org Chem. 2004;69:1235-47 pubmed..The cycloadducts derived from cyclic 2-azaallyllithium species possess the 7-azabicyclo[2.2.1]heptane (tropane) or 8-azabicyclo[3.2.1]octane ring system and have been elaborated into cocaine-like analogues. ..
- Zhang L, Wang Y, Buckingham C, Herndon J. Synthesis of furan-bridged 10-membered rings through [8 + 2]-cycloaddition of dienylfurans and acetylenic esters. Org Lett. 2005;7:1665-7 pubmed..Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene. ..
- Denmark S, Gomez L. Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. The fused/bridged mode. J Org Chem. 2003;68:8015-24 pubmed..This method converts linear polyenes to functionalized polycyclic systems bearing up to six stereogenic centers. ..
- Sugano N, Koizumi Y, Hirai G, Oguri H, Kobayashi S, Yamashita S, et al. Enantioselective synthesis of the fully functionalized ABC ring of zoanthenol. Chem Asian J. 2008;3:1549-57 pubmed publisher..The key features of the synthesis are the enzymatic kinetic optical resolution and the Mizoroki-Heck/Simmons-Smith reaction strategy used to construct the congested asymmetric quaternary carbons. ..
- Pearson W, Stoy P, Mi Y. A three-component, one-pot synthesis of indolizidines and related heterocycles via the [3+2] cycloaddition of nonstabilized azomethine ylides. J Org Chem. 2004;69:1919-39 pubmed..The same (2-azaallyl)stannanes may be transmetalated by n-butyllithium to generate 2-azaallyllithiums, which also may undergo a [3+2] cycloaddition/N-alkylation cascade to form indolizidines. ..
- Wang G, Vedejs E. Stereocontrol in N-directed hydroboration: synthesis of amino alcohols related to the piperidine alkaloids. Org Lett. 2009;11:1059-61 pubmed publisher..Comparisons with acyclic model structures show that the source of regiocontrol with the terminal alkene is due to a steric effect of the axial piperidine C(3,5) hydrogens that destabilize the competing bridged bicyclic transition state...
- Mishra L, Vilaplana R, Singh V, Yadaw A, Gonzalez Vilchez F. Nitrate/nitrite reductase activity of sulfido/selenido bridged dinuclear ruthenium(III) complexes. J Inorg Biochem. 2001;86:581-5 pubmed..The electrochemical behaviour of the complexes showed irreversible oxidation peaks at +(1.04-1.40) V quite comparable to those reported for sulphido bridged complexes. ..
- Cheng X, Waters S. Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline. Org Lett. 2010;12:205-7 pubmed publisher..Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B. ..
- Kossakowski J, Wojciechowska A. Synthesis of oxiran-2-ylmethyl and oxiran-2-ylmethoxy derivatives of some 4-azatricyclo[220.127.116.11(2,6)]dec-8-ene-3,5-diones as potential beta-adrenolytics. Acta Pol Pharm. 2006;63:485-90 pubmed..2.1.0(2,6)]dec-8-ene-3,5-dione have been prepared. The pharmacological profile of selected compounds was evaluated for their affinities at beta-adrenoceptors. The investigated compounds exhibit modest affinity for these receptors. ..
- Bunnelle W, Daanen J, Ryther K, Schrimpf M, Dart M, Gelain A, et al. Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)-bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors. J Med Chem. 2007;50:3627-44 pubmed
- Fitch R, Spande T, Garraffo H, Yeh H, Daly J. Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi. J Nat Prod. 2010;73:331-7 pubmed publisher..After synthesis, this novel rigid agonist may serve as a selective probe for beta4-containing nicotinic receptors and potentially lead to useful pharmaceuticals. ..
- Cabrera G, Butler M, Rodriguez M, Godeas A, Haddad R, Eberlin M. A sorbicillinoid urea from an intertidal Paecilomyces marquandii. J Nat Prod. 2006;69:1806-8 pubmed..The absolute stereochemistry was deduced by comparison of the CD curves with those of known members of the bisorbicillinol family. This is the first report of the isolation of a ureido sorbicillinol derivative. ..
- Martinez Junza V, Rizzi A, Jolliffe K, Head N, Paddon Row M, Braslavsky S. Conformational and photophysical studies on porphyrin-containing donor-bridge-acceptor compounds. Charge separation in micellar nanoreactors. Phys Chem Chem Phys. 2005;7:4114-25 pubmed..The data obtained with the more flexible "supermolecule" 2 showed the predicted large conformation flexibility of these molecules. ..
- Tang Q, Yang C, Liu J, Ye W, Zhao S, Lu Y, et al. [A new hetisine-type alkaloid from the stems and leaves of Aconitum coreanum]. Yao Xue Xue Bao. 2005;40:640-3 pubmed..The new alkaloid was identified on the basis of spectral analysis. Two compounds were isolated and identified as: 13-dehydro-1beta-acetyl-2alpha,6beta-dihydroxyhetisine (I) and Guanfu base G (II). Compound I is a new alkaloid. ..
- Jayasuriya H, Guan Z, Dombrowski A, Bills G, Polishook J, Jenkins R, et al. Isolation, structure, and coccidiostat activity of coccidiostatin A. J Nat Prod. 2007;70:1364-7 pubmed..The isolation, structure elucidation, relative configuration, and activity of coccidiostatin A (2) are described. ..
- Edwards D, Pritchard R, Wallace T. Fine-tuning of biaryl dihedral angles: structural characterization of five homologous three-atom bridged biphenyls by X-ray crystallography. Acta Crystallogr B. 2005;61:335-45 pubmed
- Bertolini T, Nguyen Q, Harvey D. Construction of [4.3.1]propellanes via molybdenum fischer carbene complexes. J Org Chem. 2002;67:8675-8 pubmed..The range of dienyne substrates that participate in this reaction is explored and its mechanism is analyzed and discussed. ..
- Behenna D, Stockdill J, Stoltz B. Synthesis of the carbocyclic core of zoanthenol: implementation of an unusual acid-catalyzed cyclization. Angew Chem Int Ed Engl. 2007;46:4077-80 pubmed
- Machocho A, Kiprono P, Grinberg S, Bittner S. Pentacyclic triterpenoids from Embelia schimperi. Phytochemistry. 2003;62:573-7 pubmed..Three of the triterpenoids exhibited mild antibacterial properties against the gram-positive bacterial strain Rhodococcus sp...
- Castro Rodriguez I, Olsen K, Gantzel P, Meyer K. Uranium tris-aryloxide derivatives supported by triazacyclononane: engendering a reactive uranium(III) center with a single pocket for reactivity. J Am Chem Soc. 2003;125:4565-71 pubmed..The magnetism of the series of complexes with an [N3O3-N(ax)] core structure and oxidation states +III, +IV, and +V is discussed in context of the electronic structures. ..
- He H, Pei B, Chou H, Tian T, Chan W, Lee A. Camphor sulfonyl hydrazines (CaSH) as organocatalysts in enantioselective Diels-Alder reactions. Org Lett. 2008;10:2421-4 pubmed publisher..With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels-Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 degrees C to room temperature. ..
- González Gálvez D, Garcia Garcia E, Alibés R, Bayón P, de March P, Figueredo M, et al. Enantioselective approach to Securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine. J Org Chem. 2009;74:6199-211 pubmed publisher..Moreover, since the enantioselectivity was originated by a chiral phosphine ligand, the antipode of which is readily available, the same route is expected to give access to (+)-norsecurinine and virosecurinine. ..
- Bardají G, Cantó M, Alibés R, Bayón P, Busqué F, de March P, et al. Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide. J Org Chem. 2008;73:7657-62 pubmed publisher..Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide. ..
- Liu P, Hong S, Weinreb S. Total synthesis of the Securinega alkaloid (-)-secu'amamine A. J Am Chem Soc. 2008;130:7562-3 pubmed publisher..In addition, 1H NMR NOE studies and X-ray analysis on the synthetic alkaloid have established that the indolizidine moiety is trans-fused. ..
- Ohsaki A, Kobayashi Y, Yoneda K, Kishida A, Ishiyama H. Securinega alkaloids from the wood of Securinega suffruticosa var. amamiensis. J Nat Prod. 2007;70:2003-5 pubmed..amamiensis, together with five known analogues ( 4, 6- 9). The structures 1- 3 were elucidated by spectroscopic methods including 2D NMR, and all eight compounds were evaluated for cytotoxicity against two cancer cell lines. ..
- Szostak M, AUBE J. Direct synthesis of medium-bridged twisted amides via a transannular cyclization strategy. Org Lett. 2009;11:3878-81 pubmed publisher..The sequential RCM to construct a challenging medium-sized ring followed by a transannular cyclization across a medium-sized ring delivers previously unattainable twisted amides from simple acyclic precursors. ..
- Nilsson B, Overman L, Read de Alaniz J, Rohde J. Enantioselective total syntheses of nankakurines A and B: confirmation of structure and establishment of absolute configuration. J Am Chem Soc. 2008;130:11297-9 pubmed publisher..The syntheses are sufficiently concise that gram quantities of (+)-nankakurine A (2) and (+)-nankakurine B (3) will be available for further biological studies. ..
- Han Y, Giragossian C, Mierke D, Chorev M. Ni-to-Ni+ 3-ethylene-bridged partially modified retro-inverso tetrapeptide beta-turn mimetic: design, synthesis, and structural characterization. J Org Chem. 2002;67:5085-97 pubmed
- Hirai G, Koizumi Y, Moharram S, Oguri H, Hirama M. Construction of the benzylic quaternary carbon center of zoanthenol by intramolecular Mizoroki-Heck reaction of enone. Org Lett. 2002;4:1627-30 pubmed..The cis B/C ring system was stereoselectively converted to the trans-fused framework through a SmI2-promoted deoxygenation of the alpha-hydroxy ketone. ..
- Hirasawa Y, Morita H, Kobayashi J. Nankakurine A, a novel C16N2-type alkaloid from Lycopodium hamiltonii. Org Lett. 2004;6:3389-91 pubmed..3.1]nonane ring connected to a piperidine ring through a spiro carbon, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of spectroscopic data. ..
- Saulnier M, Langley D, Frennesson D, Long B, Huang S, Gao Q, et al. Novel 3',6'-anhydro and N12,N13-bridged glycosylated fluoroindolo[2,3-a]carbazoles as topoisomerase I inhibitors. Fluorine as a leaving group from sp3 carbon. Org Lett. 2005;7:1271-4 pubmed..A novel N12,N13-bridged sugar analogue 2 results from loss of 4'-fluorine from beta-N-glycosylated analogue 4. Both analogues 1 and 2 display topo I inhibitory potencies similar to camptothecin. ..
- Nelson H, Stoltz B. Progress toward the synthesis of the basiliolides and transtaganolides: an intramolecular pyrone Diels-Alder entry into a novel class of natural products. Org Lett. 2008;10:25-8 pubmed..A highly endo-selective intramolecular pyrone Diels-Alder (IMPDA) cycloaddition rapidly constructs the tricyclic core of the basiliolides and transtaganolides. ..
- Magnus P, Padilla A. Proposed biogenetic origin of secu'amamine A from allosecurinine: a model study to support the intermediacy of the putative aziridinium ion. Org Lett. 2006;8:3569-71 pubmed..reaction: see text] A model study to support the intermediacy of the aziridinium ion in the proposed biogenetic origin of secu'amamine A from allosecurinine is described. ..
- Marrero J, Rodriguez A, Barnes C. Intricarene, an unprecedented trispiropentacyclic diterpene from the Caribbean Sea plume Pseudopterogorgia kallos. Org Lett. 2005;7:1877-80 pubmed..The unprecedented carbon skeleton of 1 constitutes a new addition to the already impressive architectural diversity of the diterpene class of marine secondary metabolites. ..
- Bunyapaiboonsri T, Yoiprommarat S, Intereya K, Rachtawee P, Hywel Jones N, Isaka M. Isariotins E and F, spirocyclic and bicyclic hemiacetals from the entomopathogenic fungus Isaria tenuipes BCC 12625. J Nat Prod. 2009;72:756-9 pubmed publisher..1 microM and cytotoxic activities against cancer cell lines (KB, BC, and NCI-H187) and nonmalignant (Vero) cells with respective IC(50) values of 15.8, 2.4, 1.6, and 2.9 microM. ..
- Chauke V, Matemadombo F, Nyokong T. Remarkable sensitivity for detection of bisphenol A on a gold electrode modified with nickel tetraamino phthalocyanine containing Ni-O-Ni bridges. J Hazard Mater. 2010;178:180-6 pubmed publisher..The poly-70-Ni(OH)TAPc modified electrode could reliably detect bisphenol A in a concentration range of 7x10(-4) to 3x10(-2)mol L(-1) with a limit of detection of 3.68x10(-9)mol L(-1). The sensitivity was 3.26x10(-4)A mol(-1) L cm(-2). ..
- Kakehi A, Suga H, Okuno H, Okuhara M, Ohta A. Preparation of new nitrogen-bridged heterocycles. 60. Syntheses and conformational analyses of bis(indolizin-1-yl) disulfides. Chem Pharm Bull (Tokyo). 2007;55:1458-65 pubmed..These three types of gauche structures were confirmed by X-ray analyses. ..
- Dyatkin A, Hoekstra W, Hlasta D, Andrade Gordon P, de Garavilla L, Demarest K, et al. Bridged bicyclic vasopressin receptor antagonists with V(2)-selective or dual V(1a)/V(2) activity. Bioorg Med Chem Lett. 2002;12:3081-4 pubmed..g., 5) and balanced dual V(1a)/V(2) (e.g., 10) compounds. Data from receptor binding, cell-based functional, and in vivo assays are presented [corrected] ..
- Coucouvanis D, Han J, Moon N. Synthesis and characterization of sulfur-voided cubanes. Structural analogues for the MoFe(3)S(3) subunit in the nitrogenase cofactor. J Am Chem Soc. 2002;124:216-24 pubmed..On the basis of this argument, a possible N(2)-binding and reduction mechanism on the FeMoco-cofactor is proposed. ..
- Pearson W, Mans D, Kampf J. Cycloadditions of nonstabilized 2-azaallyllithiums with cycloheptatriene. Org Lett. 2002;4:3099-102 pubmed..The peri- and stereoselectivity of this process are discussed. ..
- Muthusamy S, Babu S, Gunanathan C, Ganguly B, Suresh E, Dastidar P. Tandem cyclization-cycloaddition behavior of rhodium carbenoids with carbonyl compounds: stereoselective studies on the construction of novel epoxy-bridged tetrahydropyranone frameworks. J Org Chem. 2002;67:8019-33 pubmed..The calculations further revealed that a severe steric interaction caused by the phenyl rings present in dipolarophile 34 with dipole 14a increases the activation barrier of the transition state during the cycloaddition process. ..
- Yao L, AUBE J. Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams. J Am Chem Soc. 2007;129:2766-7 pubmed
- Kossakowski J, Wojciechowska A, Kozioł A. Synthesis of amino derivatives of 10-(diphenylmethylene)-4-azatricyclo[18.104.22.168(2,6)]dec-8-ene-3,5-dione as potential psychotropic and/or anti HIV agents. Acta Pol Pharm. 2006;63:261-4 pubmed..These compounds are expected to have antipsychotic and/or anti HIV activity. Molecular structure of III was confirmed by an X-ray structure analysis. The cytotoxicity and anti HIV activity of derivatives I-IV were determined. ..
- Kakehi A, Ito S, Suga H, Sakurai S, Kobayashi T. Preparation of new nitrogen-bridged heterocycles. 51. Syntheses and structures of compounds having two indolizine nuclei in a molecule. Chem Pharm Bull (Tokyo). 2001;49:1401-5 pubmed