Topic
Bicyclic molecule
About: Bicyclic molecule is a research topic. Over the lifetime, 29587 publications have been published within this topic receiving 451252 citations. The topic is also known as: bicyclic molecule.
Papers published on a yearly basis
Papers
More filters
TL;DR: In this paper, the free-radical cyclization of unsaturated cyclic β-keto esters proceeds efficiently to give bicyclic adducts, including 4-alkenyl-2-methylcyclopentane-1,3-diones bicyclo.
Abstract: Oxidative free-radical cyclizations of unsaturated β-keto esters, 1,3-diketones, and malonate diesters with 2 equiv of Mn(OAc) 3 •2H 2 O and 1 equiv of Cu(OAc) 2 •H 2 O are described. Oxidative cyclization of unsaturated cyclic β-keto esters proceeds efficiently to give bicyclic adducts. Oxidative cyclizations of 4-alkenyl-2-methylcyclopentane-1,3-diones bicyclo[3.2.1]octanediones and bicyclo[3.3.1]nonanediones
77 citations
TL;DR: It was found that those which possess a homoveratrylamino moiety exhibited superior potency and the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1.
Abstract: Substituted 1,4-benzoxazines bearing an amino side chain at the 2-position were prepared and were found to have a moderate activity on intracellular calcium. Of the compounds studied it was found that those which possess a homoveratrylamino moiety exhibited superior potency. The chain length and the nature of the amine (4-fluorophenylpiperazine, 4-fluorobenzhydryloxyethylamine, N-substituted homoveratrylamine) is discussed. The 4-benzyl-3,4-dihydro-2-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-2H-1,4-benzoxazine (3c) is the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1. Under these test conditions a ratio near 1 indicates potential intracellular calcium activity while a ratio greater than 100 an action on extracellular calcium influx.
77 citations
Patent•
26 Feb 1993
TL;DR: In this paper, the authors describe a class of compounds for the treatment of glaucoma, where carbocyclic or heterocyclics are substituted with from 1 to about 3 of loweralkoxy, lower-alkyl, loweralkylthio, lower -alkyl sulfonyl, sulfinyl, lower acid sulfonyls, hydroxy, cyano, amino, lower amino acid, dilower-alkylamino or halo; or pharmaceutically acceptable acid addition salts thereof.
Abstract: Compounds of the formula ##STR1## wherein Alk is lower-alkylene; R1 is hydrogen, lower-alkyl, Ar or ArCOO; R2 is hydrogen or lower-alkyl; R3 and R4 are the same or different hydrogen, fluoro, chloro, bromo, hydroxy, lower-alkoxy, lower-alkyl, or trifluoromethyl; Ar is phenyl, naphthyl, anthryl, 2-phenylethenyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic fused aromatic heterocyclic ring containing carbon and one or two heteroatoms independently selected from oxygen, nitrogen and sulfur, or such carbocyclic or heterocyclic rings substituted with from 1 to about 3 of lower-alkoxy, lower-alkyl, lower-alkylthio, lower-alkyl sulfinyl, lower-alkyl sulfonyl, hydroxy, cyano, amino, lower-alkylamino, dilower-alkylamino or halo; or pharmaceutically acceptable acid addition salts thereof are useful as analgesics and in the treatment of glaucoma.
77 citations
TL;DR: A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaldehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo.
77 citations
TL;DR: Overall comparison of the results indicate that 1 is subject to considerable conformational freedom and suggests that the sigma receptor is not subject to rigid stereochemical restraints with 1.
Abstract: As a continuation of our earlier study (J. Med. Chem. 1992, 35, 4334-4343) we conformationally restricted the sigma-receptor ligand 2-(1-pyrrolidinyl)-N-[2-(3,4-dichlorophenyl)ethyl]-N-methylethylamine (1) by incorporating it into a series of homologous piperazines 3-9 and homopiperazines 10 and 11, diazabicyclononanes and decanes, bridgehead bicyclooctanes and nonanes as well as other miscellaneous compounds. sigma-Receptor binding affinities were obtained using [3H](+)-pentazocine in guinea pig brain membrane sigma 1 sites. The studies suggest that the nitrogen lone pair orientation found in the piperazines affords the strongest binding interaction. Other nitrogen lone pair orientations or compounds representing unlikely staggered conformations of 1 [ as in 4-[2-(3,4-dichlorophenyl)ethyl]-1,4-diazabicyclo[3.2.2]nonane (16)] show very weak sigma interaction. Comparison of the binding data of different N-substituted homologues of 1 with those of the 1-[2-(3,4-dichlorophenyl)ethyl]-4-alkylpiperazines suggests that the two nitrogen atoms of 1 are working in opposition to one another in terms of their sensitivity to steric bulk. The high binding affinity of the 1,4-diazabicyclo[4.3.0]nonanes 12 suggests that these may approximate the methyl and pyrrolidine ring conformations found in 1 when it is bound to the sigma receptor. Compound 12 exhibited a 4-fold enantioselectivity favoring (+)-12. The synthesis of 6,7-dichloro-2-[[2-(1-pyrrolidinyl)ethyl]amino]tetralin (19) and its desmethyl derivative 20 permitted constraint of the 3,4-dichlorophenyl and N-methyl moieties of 1 into a gauche orientation. The binding data suggests that this conformation in 1 favors strong binding interaction at sigma-receptors. sigma-Receptor Ki's ranged from 0.55 nM for 1-[2-(3,4-dichlorophenyl)ethyl]-4-n-butylpiperazine (7) to 654 nM for 16. Overall comparison of the results indicate that 1 is subject to considerable conformational freedom and suggests that the sigma receptor is not subject to rigid stereochemical restraints with 1. These results add to our earlier study where we restrained 1 using simple monocyclic heterocycles.
77 citations