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
Bhandari, Kalpana
Srinivas, Nagarapu
Keshava, G. B. Shiva
Shukla, Praveen K.
[J]. 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
Emami, S
Falahati, M
Banifatemi, A
Amanlou, M
Shafiee, A
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) : 3971 - 3976
[6] Epidemiology of nosocomial fungal infections
Fridkin, SK
Jarvis, WR
[J]. 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
Gastmeier, P.
Sohr, D.
Geffers, C.
Behnke, M.
Rueden, H.
[J]. 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)
Gastmeier, P
Sohr, D
Geffers, C
Behnke, M
Daschner, F
Rüden, H
[J]. 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
Karakurt, A
Dalkara, S
Özalp, M
Özbey, S
Kendi, E
Stables, JP
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (05) : 421 - 433
[10] Oxime and oxime ether derivatives of 1,4-benzothiazine related to oxiconazole
Milanese, Lara
Giacche, Nicola
Schiaffella, Fausto
Vecchiarelli, Anna
Macchiarulo, Antonio
Fringuelli, Renata
[J]. CHEMMEDCHEM, 2007, 2 (08) : 1208 - 1213

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