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

共 23 条

[1]

[Anonymous], PLANT ALKALOIDS

[2] Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials [J].

Bhandari, Kalpana ;

Srinivas, Nagarapu ;

Keshava, G. B. Shiva ;

Shukla, Praveen K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) :437-447

[3]

DHAR ML, 1968, INDIAN J EXP BIOL, V6, P232

[4]

Dzhakhangirov FN, 1997, KHIM PRIRODNYK SOEDI, P254

[5] (E)- and (Z)-1,2,4-triazolylchromanone oxime ethers as conformationally constrained antifungals [J].

Emami, S ;

Falahati, M ;

Banifatemi, A ;

Amanlou, M ;

Shafiee, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :3971-3976

[6] Epidemiology of nosocomial fungal infections [J].

Fridkin, SK ;

Jarvis, WR .

CLINICAL MICROBIOLOGY REVIEWS, 1996, 9 (04) :499-&

[7] Risk factors for death due to nosocomial infection in intensive care unit patients:: Findings from the krankenhaus infektions surveillance system [J].

Gastmeier, P. ;

Sohr, D. ;

Geffers, C. ;

Behnke, M. ;

Rueden, H. .

INFECTION CONTROL AND HOSPITAL EPIDEMIOLOGY, 2007, 28 (04) :466-472

[8] Mortality risk factors with nosocomial Staphylococcus aureus infections in intensive care units:: Results from the German Nosocomial Infection Surveillance System (KISS) [J].

Gastmeier, P ;

Sohr, D ;

Geffers, C ;

Behnke, M ;

Daschner, F ;

Rüden, H .

INFECTION, 2005, 33 (02) :50-55

[9] Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities [J].

Karakurt, A ;

Dalkara, S ;

Özalp, M ;

Özbey, S ;

Kendi, E ;

Stables, JP .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (05) :421-433

[10] Oxime and oxime ether derivatives of 1,4-benzothiazine related to oxiconazole [J].

Milanese, Lara ;

Giacche, Nicola ;

Schiaffella, Fausto ;

Vecchiarelli, Anna ;

Macchiarulo, Antonio ;

Fringuelli, Renata .

CHEMMEDCHEM, 2007, 2 (08) :1208-1213

← 1 2 3 →