Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives

被引:215
作者
Sharma, Deepika [2 ]
Narasimhan, Balasubramanian [1 ]
Kumar, Pradeep [2 ]
Judge, Vikramjeet [2 ]
Narang, Rakesh [2 ]
De Clercq, Erik [3 ]
Balzarini, Jan [3 ]
机构
[1] Maharshi Dayanand Univ, Fac Pharmaceut Sci, Rohtak 124001, Haryana, India
[2] Guru Jambheshwar Univ Sci & Technol, Dept Pharmaceut Sci, Hisar 125001, Haryana, India
[3] Katholieke Univ Leuven, Rega Inst Med Res, Lab Virol & Chemotherapy, B-3000 Louvain, Belgium
关键词
Substituted imidazoles; Antibacterial activity; Antifungal activity; Antiviral activity; ANTIFUNGAL ACTIVITY; INHIBITORY-ACTIVITY; POTENT ACTIVITY; QSAR; ANTIBACTERIAL; DESIGN; ACID; PREDICTION;
D O I
10.1016/j.ejmech.2008.08.010
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In the present study, we have synthesized 2-(substituted phenyl)-1H-imidazole (1-12) and (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanone (13-26) analogues and screened them for their antimicrobial activity against Gram positive, Gram negative and fungal species. The results of antibacterial study indicated that compounds 15,17 and 24 showed appreciable antibacterial activity and compound 26 emerged as the most potential antifungal agent. The results of SAR studies indicated that the presence of electron withdrawing groups is necessary for the antimicrobial activity of the synthesized compounds. The results of the present study indicated that compounds 15, 17 and 24 might be of interest for the identification of new antimicrobial molecules as their antibacterial activity is equivalent to the standard drug norfloxacin. Further, the antiviral screening of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13-26) against a panel of viral strains indicated that compounds 16 and 19 can be selected as lead compounds for the development of novel antiviral agents. (C) 2008 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:2347 / 2353
页数:7
相关论文
共 41 条
[1]   Pyrimidinylimidazole inhibitors of p38: Cyclic N-1 imidazole substituents enhance p38 kinase inhibition and oral activity [J].
Adams, JL ;
Boehm, JC ;
Gallagher, TF ;
Kassis, S ;
Webb, EF ;
Hall, R ;
Sorenson, M ;
Garigipati, R ;
Griswold, DE ;
Lee, JC .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (21) :2867-2870
[2]   Substituted benzimidazoles with nanomolar activity against respiratory syncytial virus [J].
Andries, K ;
Moeremans, M ;
Gevers, T ;
Willebrords, R ;
Sommen, C ;
Lacrampe, J ;
Janssens, F ;
Wyde, PR .
ANTIVIRAL RESEARCH, 2003, 60 (03) :209-219
[3]  
[Anonymous], 2007, PHARM IND, VI, P37
[4]  
Bbizhayev MA., 2006, LIFE SCI, V78, P2343
[5]  
BHANDARI K, EUR J MED C IN PRESS
[6]  
Cappuccino J.G, 1999, Microbiology-a Laboratory Manual, V4th, P263
[7]   Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues [J].
Congiu, Cenzo ;
Cocco, Maria Teresa ;
Onnis, Valentina .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :989-993
[8]   Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes [J].
Crane, Louis ;
Anastassiadou, Maria ;
El Hage, Salome ;
Stigliani, Jean Luc ;
Baziard-Mouysset, Genevieve ;
Payard, Marc ;
Leger, Jean Michel ;
Bizot-Espiard, Jean-Guy ;
Ktorza, Alain ;
Caignard, Daniel-Henri ;
Renard, Pierre .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (22) :7419-7433
[9]   Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential [J].
Dahiya, Rajiv ;
Pathak, Devender .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (06) :772-798
[10]   Anti-enterovirus activity and structure-activity relationship of a series of 2,6-dihalophenyl-substituted 1H,3H-thiazolo[3,4-a]benzimidazoles [J].
De Palma, Armando M. ;
Heggermont, Ward ;
Leyssen, Pieter ;
Puerstinger, Gerhard ;
Wimmer, Eva ;
De Clercq, Erik ;
Rao, Angela ;
Monforte, Anna-Maria ;
Chimirri, Alba ;
Neyts, Johan .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2007, 353 (03) :628-632