Synthesis, stereochemistry and antimicrobial studies of novel oxime ethers of aza/diazabicycles

被引：51

作者：

Parthiban, Paramasivam ^{[1
,2
]}

Aridoss, Gopalakrishnan ^{[1
,2
]}

Rathika, Paramasivam ^{[3
]}

Ramkumar, Venkatachalam ^{[4
]}

Kabilan, Senthamaraikannan ^{[1
]}

机构：

[1] Annamalai Univ, Dept Chem, Annamalainagar 608002, Tamil Nadu, India

[2] Pukyong Natl Univ, Div Image Sci & Informat Engn, Pusan 608739, South Korea

[3] Annamalai Univ, Dept Microbiol, Annamalainagar 608002, Tamil Nadu, India

[4] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 24期

关键词：

3-ABN; 3,7-DABN; Oxime ether; Single crystal XRD; Stereochemistry; Antibacterial activity; Antifungal activity; NOSOCOMIAL INFECTION; SURVEILLANCE SYSTEM; ANTIFUNGAL ACTIVITY; RISK-FACTORS; OXICONAZOLE; DERIVATIVES;

D O I：

10.1016/j.bmcl.2009.10.042

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two series of bicyclic oxime ethers viz, 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one O-benzyloximes 13-24 and 2,4,6,8-tetraaryl-3,7-diazabicyclo[3.3.1]nonan-9-one O-benzyloximes 31-36 were synthesized and stereochemistry was established by their spectral (1D and 2D NMR) and crystal studies. Synthesized oxime ethers were screened for their in vitro antimicrobial activity against a set of pathogenic bacteria (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi, Escherichia coli and Klebsiella pneumoniae) and fungi (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger and Aspergillus flavus) by twofold serial dilution method, respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the molecules expressed promising antimicrobial profile against the tested pathogens and even a few compounds 16, 21, 22, 33 and 34 were better than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6981 / 6985

页数：5