The development of a methodical directional synthesis of complex organic molecules with the aim of obtaining the physiologically active substance with selective action takes a central position in modern synthetic organic chemistry. Imidazole derivatives are a key component in great many bioactive compounds of both natural and synthetic origin. Ðœany scientists in the field of pharmaceutical chemistry and pharmacology have been attracted to them in recent years. This is because of the exceptional chemical properties and biological activities that they demonstrate. It is a big challenge for the scientists to modify and synthesize new imidazole derivatives.
Romero DH, Heredia VET, GarcÃa-Barradas O, Lopez ME, Pavón ES. Synthesis of imidazole derivatives and their biological activities. J Chem Biochem. 2014, 2(2):45-83. doi: 10.15640/jcb.v2n2a3.
Lee JC, Laydon JT, McDonnell PC, Gallagher TF, Kumar S, Green D, et al. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature. 1994, 372(6508):739-46. doi: 10.1038/372739a0.
Takle AK, Brown MJ, Davies S, Dean DK, Francis G, Gaiba A, et al. The identification of potent and selective imidazole-based inhibitors of B-Raf kinase. Bioorg Med Chem Lett. 2006;16(2):378-81. doi: 10.1016/j.bmcl.2005.09.072.
Khanna IK, Weier RM, Yu Y, Xu XD, Koszyk FJ, Collins PW, et al. 1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase-2-selective, and orally active antiinflammatory agents. J Med Chem.1997; 40(11):1619-33.doi: 10.1021/jm970036a.
Lange JHM, Van Stuivenberg HH, Coolen HK, Adolfs TJP, McCreary AC, Keizer HG, et al. Bioisosteric Replacements Of The Pyrazole Moiety Of Rimonabant: Synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and imidazoles as potent and selective CB1 cannabinoid receptor antagonists. J Med Chem. 2005; 48(6):1823-38. doi: 10.1021/jm040843r.
Gallagher TF, Fier-Thompson SM, Garigipati RS, Sorenson ME, Smietana JM, Lee D, et al. 2,4,5- triarylimidazole inhibitors of IL-1 biosynthesis. Bioorg Med Chem Lett.1995; 5(11):1171-6. doi: 10.1016/0960-894X(95)00189-Z.
de Laszlo SE, Hacker C, Li B, Kim D, MacCoss M, Mantlo N, et al. Potent, orally absorbed glucagon receptor antagonists. Bioorg Med Chem Lett. 1999; 9(5):641-6. doi: 10.1016/S0960-894X(99)00081-5.
Eyers PA, Craxton M, Morrice N, Cohen P, Goedert M. Conversion of SB 203580-insensitive MAP kinase family members to drug-sensitive forms by a single amino-acid substitution. Chem Biol. 1998;5(6):321-8.doi: 10.1016/S1074-5521(98)90170-3.
Newman MJ, Rodarte JC, Benbatoul KD, Romano SJ, Zhang C, Krane S, et al. Discovery and characterization of OC144-093, a novel inhibitor of p-glycoprotein-mediated multidrug resistance. Cancer Res. 2000; 60(11):2964-72.
Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A. Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. Bioorg Med Chem Lett. 1999;9(7):1023-8. doi: 10.1016/S0960-894X(99)00112-2.
Fujioka H, Murai K, Ohba Y, Hiramastu A, Kita Y. A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes. Tetrahedron Lett. 2005; 46(13):2197-9. doi: 10.1016/j.tetlet.2005.02.025.
(a) Korshin EE, Sabirova LI, Akhadullin AG, Levin YA. Russian Chemistry Bulletin. 1994; 43:431-8. (b) Levesque G, Gressier JC, Proust M. 4,5-Dihydroimidazoles from dithiocarboxylic esters, thiocarboxamides, or nitriles. Synthesis.1981; 12:963-5. doi: 10.1055/s-1981-29659.
Vorbriiggen H, Krolikiewicz K. A simple synthesis of Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and Δ2-imidazolines. Tetrahedron Lett. 1981;22(45):4471-4.doi: 10.1016/S0040-4039(01)93017-5.
Hill AJ, Johnston JV. Amidines derived from ethylenediamine. I. Diamidines. J Am Chem Soc. 1954; 76(3): 920-2. doi: 10.1021/ja01632a092.
Boland NA, Casey M, Hynes SJ, Matthews JW, Smyth MP. A novel general route for the preparation of enantiopure imidazolines. J Org Chem. 2002; 67(11):3919-22.
Shin GI, Kim JH. A New synthetic route to poly(benzimidazole) and the related model reactions to imidazoline and benzimidazole. Bull Korean Chem Soc. 1996; 17(1):29-33. doi:
5012/bkcs
Davood A, Alipour E, Shafiee A. Efficient synthesis of imidazole derivatives: an important synthon for the preparation of biologically active compounds. Turk J Chem. 2008;32: 389 - 95.
Grimmett M. Imidazole and benzimidazole synthesis. 1st edition. Academic Press; 1997.
Lunt E, Newton CG, Smith C, Stevens GP, Stevens MF, Straw CG, et al. Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones. J Med Chem. 1987;30(2): 357- 66. doi: 10.1021/jm00385a018.
Hoffman K. Imidazoles and its derivatives. New York: Interscience; 1953. p. 143-5.
Bredereck H, Gompper R, Hayer D, Formamid -Reaktionen, XIII. Imidazole aus α-Diketonen. Chem Ber.1959; 92: 338. doi:10.1002/cber.19590920214.
Wallach O, Schuelze E. Ueber Basen der Oxalsäurereihe. Eur J Inorg Chem. 1881; 14:420-3. doi:10.1002/cber.18810140195.
Wallach O. Imidazole and its derivatives. Ber. 1876; 184:33-5.
Wallach O. Imidazole and its derivatives. Ber. 1881;14:735.
Marek A, Kulhanek J, Ludwig M, Bures F, Sirivennela B, Smarani S, et al. Facile synthesis of optically active imidazole derivatives. Molecules. 2007;12(5):1183-90. doi:10.3390/12051183.
Safari J, Khalili SD, Banitaba SH. A novel and an efficient catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles by using microwave irradiation under solvent-free conditions. J Chem Sci. 2010; 122(3):437-41. doi:10.1007/s12039-010-0051-6.
Nalage SV, Kalyankar MB, Patil VS, Bhosale SV, Deshmukh SU, Pawar RP. An efficient noncatalytic protocol for the synthesis of trisubstituted imidazole in polyethylene glycol using microwaves. Open Catalysis J. 2010; 3: 58-61. doi:10.1155/2013/512074.
Elderfield CR. Heterocyclic compounds.Vol.5. John Wiley & Sons; 1957. p.744.
Kaur N. Synthesis of fused five-membered N,N-heterocycles using microwave irradiation. Synthetic Commun Rev. 2013;45(12):1379-410. doi:10.1080/00397911.2013.828078.
Sarasin J, Wegmann E. Synthèse de l'hétéroxanthine à partir d'un dérivé de l'imidazol. Helv Chim Acta.1924; 7(1):713-9. doi:10.1002/hlca.19240070187.
Nalage SV, Kalyankar MB, Patil VS, Bhosale SV, Deshmukh SU, Pawar RP. An efficient noncatalytic protocol for the synthesis of trisubstituted imidazole in polyethylene glycol using microwaves. Open Catalysis J. 2010; 3:58-61. doi: 10.2174/1876214X01003010058.
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