In our development of drugs effective against Alzheimer's disease, we have researched a series of aromatic compounds having a characteristic cyclic amine, 1-azabicyclo[3.3.0]octane ring. In this report, we describe synthesis of a series of aromatic heterocycles with the 1-azabicyclo[3.3.0]octane ring and their pharmacological evaluation. 3-Amino-5-(1-azabicyclo[3.3.0]octan-5-yl)methyl-1,2,4-oxa...

A useful pharmaceutical intermediate, 5-nitromethyl-1-azabicyclo[3.3.0]octane (1), was prepared in one step from 1,7-dichloro-4-heptanone (4) under mild conditions. Catalytic hydrogenation of 1 over Raney Ni in the presence of sodium hydroxide afforded 5-aminomethyl-1-azabicyclo[3.3.0]octane (2) in high yield. Piracetam analogues 20-23, which were pyrrolidine derivatives involving a 1-azabicycl...

In order to develop drugs effective against Alzheimer's disease, we synthesized a series of aniline derivatives having a characteristic cyclic amine, 1-azabicyclo[3.3.0]octane ring, and evaluated their binding affinity for the central muscarinic cholinergic receptor. Among these compounds which showed high affinity to the M1 receptor, N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline (9...

This highlight review describes the syntheses of 2-azabicyclo[3.3.1]nonanes, focusing on synthetic studies macrocyclic diamine alkaloids, sarain A and madangamines. These alkaloids have a 2-azabicyclo[3.3.1]nonane that is fused with an N-heterocycle. Researchers employed unique strategies to construct different structures additional substituents functional groups in target molecule.

The halo-assisted intramolecular addition of silyl enol ethers with in situ activated lactams yielded (hydroxylated) 1-halo-8-azabicyclo[3,2,1]octane and 1-halo-9-azabicyclo[3,3,1]nonane ring systems, which provided an easy enantioselective access to 6β-silyloxytropane-3-one, 3α,6β-dihydroxytropane, and pervilleine B. The absolute configuration of the natural (-)-pervilleine B was determined to...

We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4''-nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate produc...

7-(D-5-Amino-5-carboxy-valeramido)-3-(acetylhydrazido)-8-oxo-5-thio-1-azabicyclo [4,2,0]-oct2-ene-2-carboxylic acid (1). 7-(D-5-Amino-5-carboxy-valeramido)-3-(substitutedarylacetylhydrazido)8-oxo-5-thio-1-azabicyclo[4,2,0]-oct-2-ene-2-carboxylic acid.(2-5). 7-(D-5Amino-5carboxyvaleramido)3(2'substituted aryl-3'-chloro-4'-oxo-azetidin-1'-yl)-acetylamino]-8-oxo-5-thio-1azabicyclo[4,2,0]-oct-2-ene...

We have optimized a synthetic approach to (±)-Ferrugine in 8 steps starting from 5-aminocyclohept-1-ene and using the Brønsted acid-catalyzed pseudotransannular ring-opening of epoxide derived this cycloheptene as key step for construction 8-azabicyclo[3.2.1]octane central core. While attempting enantioselective synthesis natural product enantiopure 2-hydroxy-8-azabicyclo[3.2.1]octane we found ...

The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane (4) with dimethyl dicyanofumarate ((E)-8) and dimethyl dicyanomaleate ((Z)-8) lead to the same mixture of cisand trans-4-phenyl-1-azabicyclo[2.1.1]hexane 2,3-dicarboxylates (cis-11 and trans-11, resp.; Scheme 3). This result of a formal cycloaddition to the central C-N bond of 4 is interpreted by a stepwise reaction mechanism via a relatively ...

In view of the biological activity associated with 1-azabicyclo[2.2.2]octan-3-ones, we have undertaken the synthesis and structural analysis of a series of 2-(substituted benzylidene/heteroaryl-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3ones (Sonar et al., 2003). In order to con®rm the double-bond geometry of title compound, (I), and to obtain more detailed information on the structural conformat...