Imidazole and its derivatives as potential candidates for drug development

Authors

  • Amara Mumtaz Department of Chemistry, COMSATS Institute of Information Technology Abbottabad
  • Aamer Saeed Department of Chemistry, Quaid-i-Azam University, Islamabad
  • Nighat Fatima Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad
  • Muhammad Dawood Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad
  • Hummera Rafique Department of Chemistry, University of Gujrat, Gujrat
  • Jamshed Iqbal Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad Centre for Drug Development, COMSATS Institute of Information Technology Abbottabad, Abbottabad 22-060

DOI:

https://doi.org/10.3329/bjp.v11i4.26835

Keywords:

Drug development, Imidazole, Review

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.

Downloads

Download data is not yet available.
Abstract
195
Download
111

Author Biographies

Amara Mumtaz, Department of Chemistry, COMSATS Institute of Information Technology Abbottabad

Assistant Professor

Aamer Saeed, Department of Chemistry, Quaid-i-Azam University, Islamabad

Professor

Google Scholar Citation

Nighat Fatima, Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad

Assistant Professor

Muhammad Dawood, Department of Pharmacy, COMSATS Institute of Information Technology Abbottabad

MS Scholar

Hummera Rafique, Department of Chemistry, University of Gujrat, Gujrat

Assistant Professor

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. Brønsted 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 LevenbergMarquardt 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 econo-mics. 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 anti-depressant drugs with ?2-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, Berrée 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. Anti-cancer 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 benzimidazolecoumarin 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, Müller-Bunz H, Mahal K, Münzner J, Tacke M, Mueller T, Schobert R. Gold(I)NHC complexes of antitumoral diarylimidazoles: Structures, cellular uptake routes and anti-cancer 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, characterisa-tion and electroluminescence behaviour of ?-conjugated imidazoleisoquinoline 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 imidazolecarbazole fluorophores. J Lumin. 2014b; 147: 111-20.

Özkay Y, I??kda? ?, ?ncesu Z, Akal?n 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 anti-cancer 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 deriva-tives using principal component factor analysis and genetic function approximation. Bioorgan Med Chem. 2005; 13: 2967-73.

Safari J, Gandomi-Ravandi S, Akbari Z. Sonochemical synthe-sis 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 integraseLEDGF/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 anti-oxidants 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, Müller-Bunz H, Paradisi F, Tacke M. Synthesis, cytotoxic and antibacterial studies of p-benzyl-substituted NHCsilver(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.

Uçucu Ü, Karaburun NG, I?ikda? ?. 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-?-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-iminobenzimida-zoles as potent hepatitis C virus inhibitors with a novel mechanism of action. Eur J Med Chem. 2014; 78: 35-42.

Wittine K, Stipkovi? Babi? M, Makuc D, Plavec J, Kraljevi? Paveli? S, Sedi? M, Paveli? K, Leyssen P, Neyts J, Balzarini J, Mintas M. Novel 1,2,4-triazole and imidazole derivatives of l-ascorbic and iminoascorbic 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 benzimidazole aminoesters. Eur J Med Chem. 2015; 93: 614-24.

Yurtta? L, Duran M, Demirayak ?, Gençer HK, Tunal? 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 trans-criptase 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-substi-tuted 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.

Zió?kowska 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.

Zöllinger 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.

Downloads

Published

2016-10-01

How to Cite

Mumtaz, A., A. Saeed, N. Fatima, M. Dawood, H. Rafique, and J. Iqbal. “Imidazole and Its Derivatives As Potential Candidates for Drug Development”. Bangladesh Journal of Pharmacology, vol. 11, no. 4, Oct. 2016, pp. 756-64, doi:10.3329/bjp.v11i4.26835.

Issue

Vol. 11 No. 4 (2016)

Section

Mini Review

License

Authors who publish with this journal agree to the following terms:

  1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
  2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
  3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).