Imidazole and its derivatives as potential candidates for drug development
Abstract
Imidazole and its derivatives are the pharmacological significant scaffolds with the broad spectrum of activities can be synthesized in the laboratory in the single step by the action of the catalyst. The current review summarizes the role of the imidazole and its derivatives during the last decade (2005-2014) for the treatment of many diseases. Review highlights their significant contribution towards the drug development for the treatment of some fatal diseases like HIV, cancer, tuberculosis and hepatitis C. As imidazole and its derivatives continue to play an important role for the treatment of many diseases so there is a need to trigger research in this field.
References
Anderson EB, Long TE. Imidazole- and imidazolium-containing polymers for biology and material science applications. Polymer 2010; 51: 2447-54.
Assadieskandar A, Amini M, Ostad SN, Riazi GH, Cheraghi-Shavi T, Shafiei B, Shafiee A. Design, synthesis, cytotoxic evaluation and tubulin inhibitory activity of 4-aryl-5-(3,4,5-trimethoxyphenyl)-2-alkylthio-1H-imidazole derivatives. Bioorgan Med Chem. 2013; 21: 2703-09.
Banothu J, Gali R, Velpula R, Bavantula R. Bronsted acidic ionic liquid catalyzed an efficient and eco-friendly protocol for the synthesis of 2, 4, 5-trisubstituted-1H-imidazoles under solvent-free conditions. Arabian J Chem. 2013.
Basu A, Jasu K, Jayaprakash V, Mishra N, Ojha P, Bhattacharya S. Development of CoMFA and CoMSIA models of cytotoxicity data of anti-HIV-1-phenylamino-1H-imidazole derivatives. Eur J Med Chem. 2009; 44: 2400-07.
Bellina F, Cauteruccio S, Rossi R. Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles. Tetrahedron 2007; 63: 4571-24.
Bhongade BA, Talath S, Gadad RA, Gadad AK. Biological activities of imidazo[2,1-b][1,3,4]thiadiazole derivatives: A review. J Saudi Chem Soc. 2013.
Camacho J, Barazarte A, Gamboa N, Rodrigues J, Rojas R, Vaisberg A, Gilman R, Charris J. Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents. Bioorgan Med Chem. 2011; 19: 2023-29.
Chamjangali M, Beglari M, Bagherian G. Prediction of cytotoxicity data (CC50) of anti-HIV 5-pheny-l-phenylamino-1H-imidazole derivatives by artificial neural network trained with Levenberg-Marquardt algorithm. J Mol Graph Model. 2007; 26:360-67.
Chen CL, Chang DM, Chen TC, Lee CC, Hsieh HH, Huang FC, Huang KF, Guh JH, Lin JJ, Huang HS. Structure-based design, synthesis and evaluation of novel anthra[1,2-d]imidazole-6,11-dione derivatives as telomerase inhibitors and potential for cancer polypharmacology. Eur J Med Chem. 2013a; 60: 29-41.
Chen TC, Yu DS, Huang KF, Fu YC, Lee CC, Chen CL, Huang FC, Hsieh HH, Lin JJ, Huang HS. Structure-based design, synthesis and biological evaluation of novel anthra[1,2-d]imidazole-6,11-dione homologues as potential antitumor agents. Eur J Med Chem. 2013b; 69: 278-93.
Chen X, Jia C, Wan Z, Yao X. Organic dyes with imidazole derivatives as auxiliary donors for dye-sensitized solar cells: Experimental and theoretical investigation. Dyes Pigments. 2014; 104: 48-56.
De Walque D. HIV/AIDS: Transmission, treatment, and prevention, Economics. In: Encyclopedia of health economics. Culyer AJ (ed). San Diego, Elsevier, 2014, pp 468-76.
Dostert P, Melloni P, Della Torre A, Varasi M, Merlini L, Bonsignori A, Ricciardi S. Research of potential antidepressant drugs with α2-adrenoreceptor antagonist and NA-uptake inhibiting properties: Synthesis of 2-(1-hydroxy-2-phenoxy-2-phenyl)ethyl-4,5-dihydro-1H-imidazole derivatives. Eur J Med Chem. 1990, 25: 757-63.
Fraser M, Berlin A, Ouellet V, Saad F, Bristow RG. Prostate cancer genomics as a driver of personalized medicine. In: Cancer genomics. Dellaire G, Berman JN, Arceci RJ (eds). Boston, Academic Press, 2014, pp 233-45.
Gamble C, Trotard M, Seyec JL, Abreu-Guerniou V, Gernigon N, Berree F, Carboni B, Felden B, Gillet R. Antiviral effect of ribonuclease conjugated oligodeoxynucleotides targeting the IRES RNA of the hepatitis C virus. Bioorg Med Chem Lett. 2009; 19: 3581-85.
Gong Y, Somersan Karakaya S, Guo X, Zheng P, Gold B, Ma Y, Little D, Roberts J, Warrier T, Jiang X, et al. Benzimidazole-based compounds kill Mycobacterium tuberculosis. Eur J Med Chem. 2014; 75: 336-53.
Guo J, Zhang Y, Zhang J, Liang J, Zeng L, Guo G. Anticancer effect of tert-butyl-2(4,5-dihydrogen-4,4,5,5-tetramethyl-3-O-1H-imidazole-3-cationic-1-oxyl-2)-pyrrolidine-1-carboxylic ester on human hepatoma HepG2 cell line. Chem Biol Interact. 2012; 199: 38-48.
Hwu JR, Singha R, Hong SC, Chang YH, Das AR, Vliegen I, De Clercq E, Neyts J. Synthesis of new benzimidazole-coumarin conjugates as anti-hepatitis C virus agents. Antivir Res. 2008; 77: 157-62.
Jadhav GR, Shaikh MU, Kale RP, Shiradkar MR, Gill CH. SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents. Eur J Med Chem. 2009; 44: 2930-35.
Kannan V, Sreekumar K. Clay supported titanium catalyst for the solvent free synthesis of tetrasubstituted imidazoles and benzimidazoles. J Mol Catal A Chem. 2013; 376: 34-39.
Kaps L, Biersack B, Muller-Bunz H, Mahal K, Munzner J, Tacke M, Mueller T, Schobert R. Gold(I)-NHC complexes of antitumoral diarylimidazoles: Structures, cellular uptake routes and anticancer activities. J Inorg Biochem. 2012; 106: 52-58.
Karthikeyan C, Solomon VR, Lee H, Trivedi P. Synthesis and biological evaluation of 2-(phenyl)-3H-benzo[d]imidazole-5-carboxylic acids and its methyl esters as potent anti-breast cancer agents. Arabian J Chem. 2013.
Kostakis IK, Pouli N, Marakos P, Kousidou OC, Roussidis A, Tzanakakis GN, Karamanos NK. Design, synthesis and cell growth inhibitory activity of a series of novel amino-substituted xantheno[1,2-d]imidazoles in breast cancer cells. Bioorgan Med Chem. 2008; 16: 3445-55.
Kumar R, Lown JW. Design, synthesis and in vitro cytotoxic studies of novel bis-pyrrolo[2,1][1,4] benzodiazepine-pyrrole and imidazole polyamide conjugates. Eur J Med Chem. 2005; 40: 641-54.
Li M, Kong LL, Gou Y, Yang F, Liang H. DNA binding, cytotoxicity and apoptosis induction activity of a mixed-ligand copper(II) complex with taurine Schiff base and imidazole. Spectrochim Acta A. 2014; 128: 686-93.
Li Y-F, Wang G-F, Luo Y, Huang W-G, Tang W, Feng C-L, Shi L-P, Ren Y-D, Zuo J-P, Lu W. Identification of 1-isopropyl-sulfonyl-2-amine benzimidazoles as a new class of inhibitors of hepatitis B virus. Eur J Med Chem. 2007; 42: 1358-64.
Linas BP, Hu H, Barter DM, Horberg M. Hepatitis C screening trends in a large integrated health system. Am J Med. 2014; 127: 398-405.
Liu T, Sun C, Xing X, Jing L, Tan R, Luo Y, Huang W, Song H, Li Z, Zhao Y. Synthesis and evaluation of 2-[2-(phenyl-thiomethyl)-1H-benzo[d] imidazol-1-yl)acetohydrazide derivatives as antitumor agents. Bioorg Med Chem Lett. 2012; 22: 3122-25.
Loksha YM, El-Barbary AA, El-Badawi MA, Nielsen C, Pedersen EB. Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel capravirine analogues. Bioorgan Med Chem. 2005; 13: 4209-20.
Lu X, Liu X, Wan B, Franzblau SG, Chen L, Zhou C, You Q. Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Eur J Med Chem. 2012; 49: 164-71.
Marrapu VK, Chaturvedi V, Singh S, Singh S, Sinha S, Bhandari K. Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv. Eur J Med Chem. 2011; 46: 4302-10.
May MM, Brohm D, Harrenga A, Marquardt T, Riedl B, Kreuter J, Zimmermann H, Ruebsamen-Schaeff H, Urban A. Discovery of substituted N-phenylbenzenesulphonamides as a novel class of non-nucleoside hepatitis C virus polymerase inhibitors. Antivir Res. 2012; 95: 182-91.
Mirjalili BF, Bamoniri AH, Zamani L. One-pot synthesis of 1,2, 4,5-tetrasubstituted imidazoles promoted by nano. Sci Iranica. 2012; 19: 565-68.
Moura KCG, Carneiro PF, Pinto MdCFR, da Silva JA, Malta VRS, de Simone CA, Dias GG, Jardim GAM, Cantos J, Coelho TS, et al. 1,3-Azoles from ortho-naphthoquinones: Synthesis of aryl substituted imidazoles and oxazoles and their potent activity against mycobacterium tuberculosis. Bioorgan Med Chem. 2012; 20: 6482-88.
Mungra DC, Kathrotiya HG, Ladani NK, Patel MP, Patel RG. Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]-quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents. Chinese Chem Lett. 2012; 23: 1367-70.
Nagarajan N, Prakash A, Velmurugan G, Shakti N, Katiyar M, Venuvanalingam P, Renganathan R. Synthesis, characterisation and electroluminescence behaviour of pi-conjugated imidazole-isoquinoline derivatives. Dyes Pigments. 2014a; 102: 180-88.
Nagarajan N, Vanitha G, Ananth DA, Rameshkumar A, Sivasudha T, Renganathan R. Bioimaging, antibacterial and antifungal properties of imidazole-pyridine fluorophores: Synthesis, characterization and solvatochromism. J Photoch Photobio B. 2013; 127: 212-22.
Nagarajan N, Velmurugan G, Prabhu G, Venuvanalingam P, Renganathan R. A combined experimental and theoretical investigation of imidazole-carbazole fluorophores. J Lumin. 2014b; 147: 111-20.
Ozkay Y, Isikdag I, Incesu Z, Akalin G. Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity. Eur J Med Chem. 2010; 45: 3320-28.
Park B, Awasthi D, Chowdhury SR, Melief EH, Kumar K, Knudson SE, Slayden RA, Ojima I. Design, synthesis and evaluation of novel 2,5,6-trisubstituted benzimidazoles targeting FtsZ as antitubercular agents. Bioorgan Med Chem. 2014; 22: 2602-12.
Patel HM, Noolvi MN, Sethi NS, Gadad AK, Cameotra SS. Synthesis and antitubercular evaluation of imidazo[2,1-b][1,3,4]thiadiazole derivatives. Arabian J Chem. 2013.
Premakumari C, Muralikrishna A, Padmaja A, Padmavathi V, Park SJ, Kim TJ, Reddy GD. Synthesis, antimicrobial and anticancer activities of amido sulfonamido methane linked bis heterocycles. Arabian J Chem. 2014; 7: 385-95.
Ranjith PK, Pakkath R, Haridas KR, Kumari SN. Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents. Eur J Med Chem. 2014; 71: 354-65.
Roy K, Leonard JT. QSAR by LFER model of cytotoxicity data of anti-HIV 5-phenyl-1-phenylamino-1H-imidazole derivatives using principal component factor analysis and genetic function approximation. Bioorgan Med Chem. 2005; 13: 2967-73.
Safari J, Gandomi-Ravandi S, Akbari Z. Sonochemical synthesis of 1,2,4,5-tetrasubstituted imidazoles using nano-crystalline MgAl2O4 as an effective catalyst. J Adv Res. 2013; 4: 509-14.
Saffari Jourshari M, Mamaghani M, Shirini F, Tabatabaeian K, Rassa M, Langari H. An expedient one-pot synthesis of highly substituted imidazoles using supported ionic liquid-like phase (SILLP) as a green and efficient catalyst and evaluation of their antimicrobial activity. Chinese Chem Lett. 2013; 24: 993-96.
Serrao E, Xu Z-L, Debnath B, Christ F, Debyser Z, Long Y-Q, Neamati N. Discovery of a novel 5-carbonyl-1H-imidazole-4-carboxamide class of inhibitors of the HIV-1 integrase–LEDGF/p75 interaction. Bioorgan Med Chem. 2013; 21: 5963-72.
Sharma D, Narasimhan B, Kumar P, Judge V, Narang R, De Clercq E, Balzarini J. Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. Eur J Med Chem. 2009; 44: 2347-53.
Sirisha K, Bikshapathi D, Achaiah G, Reddy VM. Synthesis, antibacterial and antimycobacterial activities of some new 4-aryl/heteroaryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyridines. Eur J Med Chem. 2011; 46: 1564-71.
Sorrenti V, Salerno L, Di Giacomo C, Acquaviva R, Siracusa MA, Vanella A. Imidazole derivatives as antioxidants and selective inhibitors of nNOS. Nitric Oxide. 2006; 14: 45-50.
Srivastava AK, Shukla N. Quantitative structure activity relationship (QSAR) studies on a series of imidazole derivatives as novel ORL1 receptor antagonists. J Saudi Chem Soc. 2013, 17: 321-28.
Streciwilk W, Cassidy J, Hackenberg F, Muller-Bunz H, Paradisi F, Tacke M. Synthesis, cytotoxic and antibacterial studies of p-benzyl-substituted NHC-silver(I) acetate compounds derived from 4,5-di-p-diisopropylphenyl- or 4,5-di-p-chlorophenyl-1H-imidazole. J Organomet Chem. 2014; 749: 88-99.
Tremblay M, Bonneau P, Bousquet Y, DeRoy P, Duan J, Duplessis M, Gagnon A, Garneau M, Goudreau N, Guse I, et al. Inhibition of HIV-1 capsid assembly: Optimization of the antiviral potency by site selective modifications at N1, C2 and C16 of a 5-(5-furan-2-yl-pyrazol-1-yl)-1H-benzimidazole scaffold. Bioorg Med Chem Lett. 2012; 22: 7512-17.
Ucucu U, Karaburun NG, Isikdag I. Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives. Il Farmaco 2001; 56: 285-90.
Ujjinamatada RK, Baier A, Borowski P, Hosmane RS. An analogue of AICAR with dual inhibitory activity against WNV and HCV NTPase/helicase: Synthesis and in vitro screening of 4-carbamoyl-5-(4,6-diamino-2,5-dihydro-1,3,5-triazin-2-yl)imidazole-1-beta-d-ribofuranoside. Bioorg Med Chem Lett. 2007; 17: 2285-88.
Windisch MP, Jo S, Kim H-Y, Kim S-H, Kim K, Kong S, Jeong H, Ahn S, No Z, Hwang JY. Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action. Eur J Med Chem. 2014; 78: 35-42.
Wittine K, Stipkovic Babic M, Makuc D, Plavec J, Kraljevic Pavelic S, Sedic M, Pavelic K, Leyssen P, Neyts J, Balzarini J, Mintas M. Novel 1,2,4-triazole and imidazole derivatives of l-ascorbic and imino-ascorbic acid: Synthesis, anti-HCV and antitumor activity evaluations. Bioorgan Med Chem. 2012; 20: 3675-85.
Xue W-J, Li H-Z, Gao F-F, Wu A. Synthesis of trisubstituted imidazoles via a convergent reaction network from methyl ketones and benzoins. Tetrahedron 2014; 70: 239-44.
Yang XD, Wan WC, Deng XY, Li Y, Yang LJ, Li L, Zhang HB. Design, synthesis and cytotoxic activities of novel hybrid compounds between 2-phenylbenzofuran and imidazole. Bioorg Med Chem Lett. 2012; 22: 2726-29.
Yoon YK, Ali MA, Wei AC, Choon TS, Ismail R. Synthesis and evaluation of antimycobacterial activity of new benzimi-dazole aminoesters. Eur J Med Chem. 2015; 93: 614-24.
Yurttas L, Duran M, Demirayak S, Gencer HK, Tunali Y. Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives. Bioorg Med Chem Lett. 2013; 23: 6764-68.
Zhan P, Liu X, Zhu J, Fang Z, Li Z, Pannecouque C, Clercq ED. Synthesis and biological evaluation of imidazole thio-acetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorgan Med Chem. 2009; 17: 5775-81.
Ziarani GM, Badiei A, Lashgari N, Farahani Z. Efficient one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetra-substituted imidazoles using SBA-Pr-SO3H as a green nano catalyst. J Saudi Chem Soc. 2013.
Ziarani GM, Dashtianeh Z, Nahad MS, Badiei A. One-pot synthesis of 1,2,4,5-tetra substituted imidazoles using sulfonic acid functionalized silica (SiO2-Pr-SO3H). Arabian J Chem. 2013.
Ziolkowska NE, Michejda CJ, Bujacz GD. Structure of HIV-1 nonnucleoside reverse transcriptase inhibitors derivatives of N-benzyl-benzimidazole with different substituents in position 4. J Mol Struct. 2010; 963: 188-93.
Zollinger M, Kelter G, Fiebig H-H, Lindel T. Antitumor activity of the marine natural product dibromophakellstatin in vitro. Bioorg Med Chem Lett. 2007; 17: 346-49.
Zoraghi R, Reiner NE. Protein interaction networks as starting points to identify novel antimicrobial drug targets. Curr Opin Microbiol. 2013; 16: 566-72.
