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

Medicinal Chemistry Research

Volumn 18, Issue 3, 2009, Pages 221-230

  Gaonkar, S L ^a   Lokanatha Rai, K M ^a   Suchetha Shetty, N ^b  

^a UNIVERSITY OF MYSORE   (India)

^b NITTE DEEMED TO BE UNIVERSITY   (India)

Author keywords

Anti inflammatory; Imidazole carbaldehyde; Microwave irradiation

Indexed keywords

2 BUTYL 5 CHLORO 3 (3,5 DIMETHYLISOXAZOL 4 YLMETHYL) 3H IMIDAZOLE 4 CARBALDEHYDE; 2 BUTYL 5 CHLORO 3 (4 NITROBENZYL) 3H IMIDAZOLE 4 CARBALDEHYDE; 2 BUTYL 5 CHLORO 3H IMIDAZOLE 4 CARBALDEHYDE DERIVATIVE; ANTIINFLAMMATORY AGENT; BENZYL DERIVATIVE; CARRAGEENAN; FUNCTIONAL GROUP; IBUPROFEN; IMIDAZOLE DERIVATIVE; ISOXAZOLE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; MALE; MICROWAVE RADIATION; NONHUMAN; PAW EDEMA; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SUBSTITUTION REACTION;

EID: 68849088802     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9121-4     Document Type: Article

References (23)

1. 2-3-imidazolepropionic acid Tetrahedron Lett 35 3045 10.1016/S0040-4039(00)76823-7 (Pubitemid 24162668)
2. DJ Carini JV Duncia PE Aldrich AT Chiu 1991 Nonpeptide angiotensin II receptor antagonists: the discovery of a series of N-(biphenylylmethyl) imidazoles as potent, orally active antihypertensives J Med Chem 34 2525 10.1021/jm00112a031
3. R Dagani 1988 Polymer technology in ceramics Chem Eng News 66 7
4. SL Gaonkar HS Yathirajan B Nagaraj RS Narasegowda 2004 2-Butyl-4-chloro-1-(4-nitrobenzyl)-1H-imidazole-5-carboxaldehyde Acta Crystallogr E 60 2520 10.1107/S1600536804031162 (Pubitemid 40649194)
5. A Gourdenne AH Maassarani P Manchaux S Aussudre 1979 Applications of microwave in polymer technology Polm Prepr 20 471
6. GJ Griffiths MB Hauck R Imwinkelried J Kohr 1999 Novel Syntheses of 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde: a key Intermediate for the synthesis of the angiotensin II antagonist Losartan J Org Chem 64 8084 10.1021/jo9824910 (Pubitemid 29529211)
7. DE Griswold PJ Marshall JC Lee EF Webb 1991 Pharmacology of the pyrroloimidazole, SK&F 105809-II: antiinflammatory activity and inhibition of mediator production in vivo Biochem Pharmacol 42 825 10.1016/0006-2952(91) 90042-4
8. NS Günay GN Ulusoy N Ergenç G Ötük 1999 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents Farmaco 54 826 10.1016/S0014-827X(99)00109-3 (Pubitemid 30009675)
9. P Gupta S Hameed R Jain 2004 Ring-substituted imidazoles as a new class of anti-tuberculosis agents Eur J Med Chem 39 805 10.1016/j.ejmech.2004.05.005 (Pubitemid 39165165)
10. RM Keenan J Weinstock JA Finkelstein RG Franz 1993 Potent nonpeptide angiotensin II receptor antagonists J Med Chem 38 1880 10.1021/jm00065a011
11. Khabnadideh S, Rezaei Z, Khalafi-Nezhad A, Bahrinajafi R et al (2003) Synthesis of N-alkylated derivatives of imidazole as antibacterial agents. Bioorg Med Chem Lett 13:2863. doi: 10.1016/S0960-894X(03)00591-2 (Pubitemid 37386239)
12. S Knapp J Albaneze HJ Schugar 1993 The beneficial effect of imidazole ligands on (.pi.-allyl)nickel coupling J Org Chem 58 997 10.1021/jo00057a006
13. SA Laufer HG Striegel GK Wagner 1993 Imidazole inhibitors of cytokine release: probing substituents in the 2 position J Med Chem 45 4695 10.1021/jm020873z
14. BH Lipshutz 1986 Five-membered heteroaromatic rings as intermediates in organic synthesis Chem Rev 86 795 10.1021/cr00075a005
15. A Miyazaki C Yokouchi M Takada 1989 External control of drug release. Controlled release of 5-fluorouracil from a hydrophilic polymer matrix by microwave irradiation Chem Pharma Bull Jpn 37 208
16. P Schiatti D Selva G Galliani E Baldoli 1986 Highly selective antiinflammatory and analgesic activity of 3-(1-methylethyl)-2-(4-methoxyphenyl) -3H-naphth[1, 2-d]imidazole, a new non-acidic molecule Arzneimittelforschung 36 102
17. DH Slee SJ Romano J Yu TN Nguyen 2001 Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with antiinflammatory activity J Med Chem 44 2094 10.1021/jm000508c (Pubitemid 32861770)
18. Z Soyer F Sultan KK Erol V Pabuçcuolu 2004 Synthesis and anticonvulsant activity of some ω-(1H-imidazol-1-yl)-N-phenylacetamide and propionamide derivatives Farmaco 59 595 10.1016/j.farmac.2003.07.011 (Pubitemid 38950766)
19. Kakinuma H Toshio H Umemiya H Amada 2004 Imidazole derivatives as new potent and selective 20-HETE synthase inhibitors Bioorg Med Chem Lett 14 333 10.1016/j.bmcl.2003.11.005 (Pubitemid 38045117)
20. MY Tse MC Depew JK Wan 1990 Highly effective methane conversion to aromatic hydrocarbons Res Chem Intermed 13 221 10.1163/156856790X00102
21. U Ümit G Nalan lhan I Karaburun 2001 Synthesis and analgesic activity of some 1-benzyl-2-substituted-4, 5-diphenyl-1H-imidazolederivatives Farmaco 56 285 10.1016/S0014-827X(01)01076-X (Pubitemid 32463311)
22. Vanelle P, Meuche J, Maldonado J, Crozet MP et al (2000) [1,3]dioxol-5-yl-1-methyl-1H-imidazole-2-carbaldehyde and evaluation of leishmanicidal activity. Eur J Med Chem 35:157. doi: 10.1016/S0223-5234(00) 00106-9 (Pubitemid 30136697)
23. CA Winter EA Risley GW Nuss 1962 Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs Proc Soc Exp Biol NY 111 544