Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles

被引：64

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, Chidambaram, India

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

[3] Annamalai Univ, Dept Microbiol, Annamalainagar 608002, Chidambaram, India

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 11期

关键词：

Heterocycles; Oxime ethers; Stereochemistry; Antibacterial activity; Antifungal activity; ANTIFUNGAL ACTIVITY; OXICONAZOLE; STEREOCHEMISTRY; PIPERIDIN-4-ONE; ANTIBACTERIAL;

D O I：

10.1016/j.bmcl.2009.04.038

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2981 / 2985

页数：5

共 27 条

[1] Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies [J].

Aridoss, G. ;

Parthiban, R. ;

Ramachandran, R. ;

Prakash, M. ;

Kabilan, S. ;

Jeong, Yeon Tae .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (02) :577-592

[2] Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones [J].

Aridoss, G. ;

Balasubramanian, S. ;

Parthiban, P. ;

Kabilan, S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (06) :851-860

[3] A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives [J].

Aridoss, Gopalakrishnan ;

Amirthaganesan, Shanmugasundaram ;

Kumar, Nanjundan Ashok ;

Kim, Jong Tae ;

Lim, Kwon Taek ;

Kabilan, Senthamaraikannan ;

Jeong, Yeon Tae .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (24) :6542-6548

[4] SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].

BALIAH, V ;

JEYARAMAN, R ;

CHANDRASEKARAN, L .

CHEMICAL REVIEWS, 1983, 83 (04) :379-423

[5] 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

[6] GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].

CREMER, D ;

POPLE, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358

[7]

Dell CP, 1998, CURR MED CHEM, V5, P179

[8]

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

[9] (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

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

Fridkin, SK ;

Jarvis, WR .

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

← 1 2 3 →