Microwave-assisted synthesis and evaluation of anti-inflammatory activity of new series of N-substituted 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde derivatives

被引:22
作者
Gaonkar, S. L. [1 ]
Rai, K. M. Lokanatha [1 ]
Shetty, N. Suchetha [2 ]
机构
[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India
[2] Justice KS Hegde Med Acad, Dept Biochem, Mangalore 574160, India
关键词
Anti-inflammatory; Imidazole-carbaldehyde; Microwave irradiation; IMIDAZOLE; ANTIBACTERIAL; POTENT;
D O I
10.1007/s00044-008-9121-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of N-substituted 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde derivatives bearing potentially bioactive substituents were synthesized by microwave irradiation method in good yield compared with conventional method. The synthesized compounds were screened for their anti-inflammatory activity and were compared with a standard drug. The compounds demonstrated potent to weak anti-inflammatory activity. Of the compounds studied, compounds 6i and 6d showed potent activity comparable to the standard drug ibuprofen at the same dose in carrageenan-induced paw edema in rat model.
引用
收藏
页码:221 / 230
页数:10
相关论文
共 23 条
[1]   NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - THE DISCOVERY OF A SERIES OF N-(BIPHENYLYLMETHYL)IMIDAZOLES AS POTENT, ORALLY ACTIVE ANTIHYPERTENSIVES [J].
CARINI, DJ ;
DUNCIA, JV ;
ALDRICH, PE ;
CHIU, AT ;
JOHNSON, AL ;
PIERCE, ME ;
PRICE, WA ;
SANTELLA, JB ;
WELLS, GJ ;
WEXLER, RR ;
WONG, PC ;
YOO, SE ;
TIMMERMANS, PBMWM .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2525-2547
[2]  
DAGANI R, 1988, CHEM ENG NEWS, V66, P7
[3]   2-Butyl-4-chloro-1-(4-nitrobenzyl)-1H-imidazole-5-carboxaldehyde [J].
Gaonkar, SL ;
Yathirajan, HS ;
Nagaraj, B ;
Narasegowda, RS ;
Lynch, DE .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 :O2520-O2521
[4]  
Gourdenne A., 1979, Polym. Prepr. (Am. Chem. Soc, V20, P471
[5]   Novel syntheses of 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde:: A key intermediate for the synthesis of the angiotensin II antagonist Losartan [J].
Griffiths, GJ ;
Hauck, MB ;
Imwinkelried, R ;
Kohr, J ;
Roten, CA ;
Stucky, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8084-8089
[6]   PHARMACOLOGY OF THE PYRROLOIMIDAZOLE, SK-AND-F-105809 .2. ANTIINFLAMMATORY ACTIVITY AND INHIBITION OF MEDIATOR PRODUCTION INVIVO [J].
GRISWOLD, DE ;
MARSHALL, PJ ;
LEE, JC ;
WEBB, EF ;
HILLEGASS, LM ;
WARTELL, J ;
NEWTON, J ;
HANNA, N .
BIOCHEMICAL PHARMACOLOGY, 1991, 42 (04) :825-831
[7]   5-Nitroimidazole derivatives as possible antibacterial and antifungal agents [J].
Günay, NS ;
Capan, G ;
Ulusoy, N ;
Ergenç, N ;
Ötük, G ;
Kaya, D .
FARMACO, 1999, 54 (11-12) :826-831
[8]   Ring-substituted imidazoles as a new class of anti-tuberculosis agents [J].
Gupta, P ;
Hameed, S ;
Jain, R .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (09) :805-814
[9]   GUANOSINE DERIVATIVES BEARING AN N-2-3-IMIDAZOLEPROPIONIC ACID [J].
HEEB, NV ;
BENNER, SA .
TETRAHEDRON LETTERS, 1994, 35 (19) :3045-3048
[10]   POTENT NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS .2. 1-(CARBOXYBENZYL)IMIDAZOLE-5-ACRYLIC ACIDS [J].
KEENAN, RM ;
WEINSTOCK, J ;
FINKELSTEIN, JA ;
FRANZ, RG ;
GAITANOPOULOS, DE ;
GIRARD, GR ;
HILL, DT ;
MORGAN, TM ;
SAMANEN, JM ;
PEISHOFF, CE ;
TUCKER, LM ;
AIYAR, N ;
GRIFFIN, E ;
OHLSTEIN, EH ;
STACK, EJ ;
WEIDLEY, EF ;
EDWARDS, RM .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (13) :1880-1892