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.
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101 citations
TL;DR: Among the different heterocyclic rings, the N-substituted indole ring is shown to be more conducive to both the activities than any other ring, however, a 5-membered ring is indicated to be less effective than a 9- or 10- Membered ring for activity B.
101 citations
TL;DR: In this article, a simple enantioselective synthesis of sirenin (bioactive form) has been developed which depends on the intramolecular cycloaddition reaction of diazo ester 5 to form bicyclic ester 6 (95 : 5 enantiosity) using a new and remarkably stable monomeric chiral Cu(I) complex whose structure was proven by X-ray diffraction analysis.
101 citations
101 citations
TL;DR: Bicyclic analogues designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation may represent important new structural motifs for the development of p56lck inhibitors.
Abstract: A study was undertaken to prepare inhibitors of the lymphocyte protein-tyrosine kinase p56lck. Using the known p56lck inhibitor 3,4-dihydroxy-alpha-cyanocinnamamide (4) as a lead compound, bicyclic analogues were designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation. Such planarity was rationalized to be an important determinant for binding within a putative flat, cleftlike catalytic cavity. Bicyclic analogues were prepared using the naphthalene, quinoline, isoquinoline, and 2-iminochromene ring systems and examined for their ability to inhibit autophosphorylation of immunopurified p56lck. The most potent analogues were methyl 7,8-dihydroxyisoquinoline-3-carboxylate (12) (IC50 = 0.2 microM) and 7,8-dihydroxyisoquinoline-3-carboxamide (13) (IC50 = 0.5 microM). Inhibition by 12 was not competitive with respect to ATP. These compounds may represent important new structural motifs for the development of p56lck inhibitors.
101 citations