Conventional and microwave-assisted synthesis of imidazole and guanidine derivatives and their biological evaluation

Medicinal Chemistry Research

Volumn 20, Issue 7, 2011, Pages 887-897

  Sondhi, Sham M ^a   Singh, Jaiveer ^a   Roy, Partha ^a   Agrawal, S K ^b   Saxena, A K ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

^b CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Anti inflammatory; Anticancer; Guanidine; Imidazole; Microwave irradiation

Indexed keywords

1 (1H BENZO[D]IMIDAZOL 2 YL) 3 ((1 METHYL 1H PYRROL 2 YL)METHYLENE)GUANIDINE; 1 (1H BENZO[D]IMIDAZOL 2 YL) 3 ((2 HYDROXYNAPHTHALEN 1 YLMETHYLENE)GUANIDINE; 1 (1H BENZO[D]IMIDAZOL 2 YL) 3 ((3 METHYLTHIOPHEN 2 YL)METHYLENE)GUANIDINE; 1 (1H BENZO[D]IMIDAZOL 2 YL) 3 ((5 METHYLTHIOPHEN 2 YL)METHYLENE)GUANIDINE; 1 (1H BENZO[D]IMIDAZOL 2 YL) 3 (NAPHTHALEN 1 YLMETHYLENE)GUANIDINE; 1 (1H BENZO[D]IMIDAZOL 2 YL) 3 (NAPHTHALEN 2 YLMETHYLENE)GUANIDINE; 1 NAPHTHALDEHYDE; 2 (1 METHYL 1H PYRROL 2 YL) 1H ANTHRA[1,2 D]IMIDAZOLE 6,11 DIONE; 2 (1 METHYL 1H PYRROL 2 YL) 1H IMIDAZO[4,5 B]PHENAZINE; 2 (1H IMIDAZO[4,5 B]PHENAZIN 2 YL)NAPHTHALEN 2 OL; 2 (2 HYDROXYNAPHTHALEN 1 YL) 1H ANTHRA[1,2 D]IMIDAZOLE 6,11 DIONE; 2 (3 METHYLTHIOPHEN 2 YL) 1H IMIDAZO[4,5 B]PHENAZINE; 2 (3 METHYLTHIOPHEN 2YL) 1H ANTHRA[1,2 D]IMIDAZOLE 6,11 DIONE; 2 (5 METHYLTHIOPHEN 2 YL) 1H IMIDAZO[4,5 B]PHENAZINE; 2 (5 METHYLTHIOPHEN 2YL) 1H ANTHRA[1,2 D]IMIDAZOLE 6,11 DIONE; 2 (NAPHTHALEN 1 YL) 1H IMIDAZO[4,5 B]PHENAZINE; 2 (NAPHTHALEN 2 YL) 1H IMIDAZO[4,5 B]PHENAZINE; 2 (NAPHTHALENE 1 YL) 1H ANTHRA[1,2 D]IMIDAZOLE 6,11 DIONE; 2 (NAPHTHALENE 2 YL) 1H ANTHRA[1,2 D]IMIDAZOLE 6,11 DIONE; 2 GUANIDINOBENZIMIDAZOLE; 2 HYDROXY 1 NAPHTHALDEHYDE; 2 NAPHTHALDEHYDE; 3 METHYLTHIOPHEN 2 CARBOXALDEHYDE; 5 METHYLTHIOPHEN 2 CARBOXALDEHYDE; ALDEHYDE DERIVATIVE; GUANIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; N METHYLPYRROL 2 CARBOXALDEHYDE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; FEMALE; HEATING; HUMAN; HUMAN CELL; MALE; MICROWAVE IRRADIATION; NONHUMAN; RAT; SYNTHESIS;

EID: 80054726092     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9410-6     Document Type: Article

References (22)

1. Albrecht W, Hauser D, Laufer S, Striegel H-G, Tollmann K (2008) Imidazole derivatives as antiinflammatory agents and their preparation, pharmaceutical compositions and use in the treatment of inflammation associated with immune system impairment. PCT International Application WO 2008023066, Chem. Abstr. 148, 308343
2. Bevec D (2004) Pyrimidinium-guanidiniminoethylphenyl-guanidinoalkyl amines and guanidiniminoethylphenyl-guanidinoalkylamines as pharmaceutically active new substances for the treatment of viral infections and other conditions. European patent application EP 1413300, Chem. Abstr. 140, 350626
3. Brzozowski Z, Saczewski F, Slawinski J (2007) Synthesis of novel 3-amino-2-(4-chloro-2-mercaptobenzenesulfonyl)-guanidine derivatives as potential antitumor agents. Eur J Med Chem 42: 1218-1225. doi:10.1016/j.ejmech. 2007.01.020 (Pubitemid 47241265)
4. Courtney SM, Hay PA, Scopes DIC (2004) Preparation of benzoxazole, benzothiazole and benzimidazole acid derivatives for the treatment of cancer. PCT International Application WO 2004046122, Chem. Abstr. 141, 7114
5. Ersan S, Nacak S, Noyanalplan N, Yesilada E (1997) Studies on analgesic and antiinflammatory activities of 1-dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives. Arzneimittel-Forschung 47:834-836 (Pubitemid 27319884)
6. Gaonkar SL, Lokanatha RKM, Suchetha SN (2009) Microwaveassisted synthesis and evaluation of anti-inflammatory activity of new series of N-substituted 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde derivatives. Med Chem Res 18:221-230. doi: 10.1007/s00044-008-9121-4
7. Gislason GH, Rasmussen JN, Abildstrom SZ, Schramm TK, Hansen ML, Fosbol EL, Sorensen R, Folke F, Buch P, Gadsboll N, Rasmussen S, Poulsen HE, Kober L, Madsen M, Torp-Pedersen C (2009) Increased mortality and cardiovascular morbidity associated with use of nonsteroidal anti-inflammatory drugs in chronic heart failure. Arch Intern Med 169:141-149
8. Gupta P, Hameed S, Jain R (2004) Ring-substituted imidazoles as a new class of anti-tuberculosis agents. Eur J Med Chem 39:805-814. doi:10.1016/j.ejmech.2004.05.005 (Pubitemid 39165165)
9. Havaldar FH, Patil AR (2008) Synthesis of biologically active 1-[2-(2-methyl-5-nitroimidazol-1-yl)acetyl]-3-substituted phenyl-4-carbaldehyde- 1H-pyrazoles. Asian J Chem 20:97-101
10. Hensler ME, Bernstein G, Nizet V, Nefzi A (2006) Pyrrolidine biscyclic guanidines with antimicrobial activity against drugresistant Gram-positive pathogens identified from a mixturebased combinatorial library. Bioorg Med Chem Lett 16:5073-5079. doi:10.1016/j.bmcl.2006.07.037 (Pubitemid 44247706)
11. Herrero MA, Kremsner JM, Kappe CO (2008) Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry. J Org Chem 73:36-47
12. Matasova LV, Kryl'skii DV, Popova TN, Makeeva AV, Shikhaliev KS (2008) Cardioprotective properties of benzoxy(thia)azol guanidine derivatives. Farmatsevticheskoi Khimii 56
13. Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 83:757-766
14. Oezden S, Atabey D, Yildiz S, Goeker H (2005) Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5- carboxylatesderivatives carryingamide or amidine groups. Bioorg Med Chem 13:1587-1597. doi:10.1016/j.bmc.2004.12.025 (Pubitemid 40215246)
15. Pearce AN, Chia EW, Berridge MV, Maas EW, Page MJ, Harper JL, Webb VL, Copp BR (2008) Orthidines A-E, tubastrine, 3,4-dimethoxyphenethyl-b-guanidine, and 1,14-sperminedihomovanillamide: Potential anti-inflammatory alkaloids isolated from the New Zealand ascidian Aplidium orthium that act as inhibitors of neutrophil respiratory burst. Tetrahedron 64:5748-5755. doi: 10.1016/j.tet.2008.04.012
16. Sircar JC, Thomas RJ, Richards ML, Khatuya H (2004) Preparation of imidazole derivatives for treatment of allergic and hyperproliferative disorders. PCT International Application WO 2004091610, Chem. Abstr., 141, 395552
17. Skehan P, Storeng R, Scudiero D, Monks A, McMohan J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107-1112 (Pubitemid 20213250)
18. Sondhi SM, Rani R (2008) A convenient, solvent free and high yielding synthesis of bicyclo-heterocyclic compounds. Lett Org Chem 5:51-54. doi:10.2174/157017808783330180
19. Sondhi SM, Rani R, Gupta PP, Agrawal SK, Saxena AK (2009a) Synthesis, anticancer, and anti-inflammatory activity evaluation of methanesulfonamide and amidine derivatives of 3,4-diaryl-2-imino-4-thiazolines. Mol Divers 13:357-366
20. Sondhi SM, Rani R, Roy P, Agrawal SK, Saxena AK (2009b) Microwave-assisted synthesis of N-substituted cyclic imides and their evaluation for anticancer and anti-inflammatory activities. Bioorg Med Chem Lett 19:1534-1538. doi:10.1016/j.bmcl. 2008.07.048
21. Sondhi SM, Singh J, Kumar A, Jamal H, Gupta PP (2009c) Synthesis of amidine and amide derivatives and their evaluation for antiinflammatory and analgesic activities. Eur J Med Chem 44:1010-1015. doi:10.1016/j.ejmech.2008.06. 029
22. Winter CA, Risley EA, Nuss GW (1962) Carrageenin-induced edema in hind paw of rat as an assay for antiinflammatory drugs. Proc Soc Exp Biol Med 111:544-547