Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives

European Journal of Medicinal Chemistry

Volumn 79, Issue , 2014, Pages 194-202

  Kalalbandi, Veerendra Kumar A ^a   Seetharamappa, J ^a   Katrahalli, Umesha ^a   Bhat, Kishore G ^b  

^a KARNATAK UNIVERSITY   (India)

^b Maratha Mandal's NGH Institute of Dental Sciences and Research Centre   (India)

Author keywords

1H benzimidazoles; Anti tuberculosis; Crystal structure; Cytotoxic activity

Indexed keywords

1 (1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 (2 (CHLOROMETHYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 (2 METHYL 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2EN 1 ONE; 1 (2 METHYL 6 NITRO 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 (5,6 DIMETHYL 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 (6 METHYL 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 (6 NITRO 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [ 3 PHENYLPROP 2 ENOYL] 1H BENZIMIDAZOLE DERIVATIVE; 1 [2 (2 CHLOROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (2 HYDROXYPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (2 NITROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (3 BROMOPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (3 CHLOROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (3 NITROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (3,4 DICHLOROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (4 CHLOROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (4 FLUOROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (4 HYDROXYPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (4 METHOXYPHENYL) 1H BENZO[D]IMIDAZOL 1 YL] 3 PHENYLPROP 2 EN 1 ONE; 1 [2 (4 NITROPHENYL) 1H BENZO[D]IMIDAZOL 1 YL) 3 PHENYLPROP 2 EN 1 ONE; 3 PHENYL 1 (2 PHENYL 1H BENZO[D]IMIDAZOL 1 YL)PROP 2 EN 1 ONE; 3 PHENYL 1 [2 (P TOLYL) 1H BENZO[D]IMIDAZOL 1 YL) PROP 2 EN 1 ONE; BENZIMIDAZOLE DERIVATIVE; CARBON; PYRAZINAMIDE; RIFAMPICIN; STREPTOMYCIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; CYTOTOXIN;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOLYSIS; DRUG CYTOTOXICITY; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; MOLECULE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RESAZURIN ASSAY; X RAY DIFFRACTION; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL CULTURE;

ANTITUBERCULAR AGENTS; CELL PROLIFERATION; CYTOTOXINS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84898649064     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.04.017     Document Type: Article

References (36)

1. World Health Organization, Global Tuberculosis Report 2012, http://www.who.int/tb/publications/global-report/gtbr12-executivesummary.pdf (last accessed on 21.10.13)
2. C. Dye Global epidemiology of tuberculosis The Lancet 367 2006 938 940
3. C. Dye, K. Lonnroth, E. Jaramillo, B.G. Williams, and M. Raviglione Trends in tuberculosis incidence and their determinants in 134 countries Bulletin of the World Health Organization 87 2009 683 691
4. H. Tomioka Current status of some antituberculosis drugs and the development of new antituberculous agents with special reference to their in vitro and in vivo antimicr (Pubitemid 44669760)
5. M.K. Spigelman New tuberculosis therapeutics: a growing pipeline Journal of Infectious Diseases 196 2007 28 34
6. A.M. Ginsberg, and M. Spigelman Challenges in tuberculosis drug research and development Natural Medicines 13 2007 290 294 (Pubitemid 46376672)
7. Z. Ma, C. Lienhardt, H. McIlleron, A.J. Nunn, and X. Wang Global tuberculosis drug development pipeline: the need and the reality Lancet 375 2010 2100 2109
8. C. Lienhardt, A. Vernon, and M.C. Raviglione New drugs and new regimens for the treatment of tuberculosis: review of the drug development pipeline and implications for national programmes Current Opinion in Pulmonary Medicine 16 2010 186 193
9. Beena, and D.S. Rawat Antituberculosis drug research: a critical overview Medicinal Research Reviews 33 2013 693 764
10. K. Kumar, D. Awasthi, S.Y. Lee, I. Zanardi, B. Ruzsicska, S. Knudson, P.J. Tonge, R.A. Slayden, and I. Ojima Novel trisubstituted benzimidazoles, targetting Mtb FtsZ, as a new class of antitubercular agents Journal of Medicinal Chemistry 54 2011 374 381
11. M.J. O'Niel, M. Smith, and P.E. Heckelman The Merck Index thirteenth ed. 2001 Merck & Co. Inc. New Jersey 1785
12. V.M. Reddy, and K.R. Reddy Synthesis and antimicrobial activity of some novel 4-(1H-benz[d]imidazol-2yl)-1,3-thiazol-2-amines Chemical and Pharmaceutical Bulletin 58 2010 953 956
13. V. Klimešova, J. Koci, K. Waisser, and J. Kaustova New benzimidazole derivatives as antimycobacterial agents Il Farmaco 57 2002 259 265 (Pubitemid 34257935)
14. M. Pieroni, S.K. Tipparaju, S. Lun, Y. Song, A.W. Sturm, W.R. Bishai, and A.P. Kozikowski Pyrido[1,2-a]benzimidazole-based agents active against tuberculosis (TB), multidrug-resistant (MDR) TB and extensively drug-resistant (XDR) TB ChemMedChem 6 2011 334 342 Special Issue: Rare & Neglected Diseases
15. M.M. Ramla, M.A. Omar, A.M.M. El-Khamry, and H.I. El-Diwani Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles Bioorganic & Medicinal Chemistry 14 2006 7324 7332 (Pubitemid 44403102)
16. M.M. Ramla, M.A. Omar, H. Tokuda, and H.I. El-Diwani Synthesis and inhibitory activity of new benzimidazole derivatives against Burkitt's lymphoma promotion Bioorganic & Medicinal Chemistry 15 2007 6489 6496 (Pubitemid 47212728)
17. S. Demirayak, U.A. Mohsen, and A.C. Karaburun Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives European Journal of Medicinal Chemistry 37 2002 255 260 (Pubitemid 34251188)
18. A.A.E. Rashedy, and H.Y.A. Enein Benzimidazoles derivatives as potential anticancer agents Mini-Reviews in Medicinal Chemistry 13 2013 399 407
19. K.D. Thomas, A.V. Adhikari, I.H. Chowdhury, E. Sumesh, and N.K. Pal New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents European Journal of Medicinal Chemistry 46 2011 2503 2512
20. S. Sharma, P.K. Sharma, N. Kumar, and R. Dudhe A review on various heterocyclic moieties and their antitubercular activity Biomedicine & Pharmacotherapy 65 2011 244 251
21. E.L. White, L.J. Ross, R.C. Reynolds, L.E. Seitz, G.D. Moore, and D.W. Borhani Slow polymerization of Mycobacterium tuberculosis FtsZ Journal of Bacteriology 182 2000 4028 4034 (Pubitemid 30436565)
22. A.D. Khoje, C. Charnock, B. Wan, S. Franzblau, and L.L. Gundersen Synthesis and antimycobacterial activities of non-purine analogs of 6-aryl-9-benzylpurines: imidazopyridines, pyrrolopyridines, benzimidazoles, and indoles Bioorganic & Medicinal Chemistry 19 2011 3483 3491
23. H. Xiangming, M. Huiqiang, and W. Yulu p-TsOH catalyzed synthesis of 2-arylsubstituted benzimidazoles Arkivoc (Archive for Organic Chemistry) 2007 150 154 xiii
24. T. Nemoto, T. Ohshima, and M. Shibasaki Catalytic asymmetric synthesis of α,β-epoxy esters, aldehydes, amides, and γ,δ-epoxy β-keto esters: unique reactivity of α, β-unsaturated carboxylic acid imidazolides Journal of the American Chemical Society 123 2001 9474 9475 (Pubitemid 32900330)
25. Oxfordshire, England Oxford Diffraction Ltd., Xcalibur CCD System, CrysAlis Software System Version 1.171.34.40 Abingdon 2008
26. G.M. Sheldrick A short history of SHELX Acta Crystallographica Section A 64 2008 112
27. M. Kratky, J. Vinsova, E. Novotna, J. Mandikova, V. Wsol, F. Trejtnar, V. Ulmann, J. Stolarikova, S. Fernandes, S. Bhat, and J.O. Liu Salicylanilide derivatives block Mycobacterium tuberculosis through inhibition of isocitrate lyase and methionine aminopeptidase Tuberculosis 92 2012 434 439
28. R.B. Pathak, P.T. Chovatia, and H.H. Parekh Synthesis antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives Bioorganic & Medicinal Chemistry Letters 22 2012 5129 5133
29. A. Garcia, V. Bocanegra-Garcia, J.P. Palma-Nicolas, and G. Rivera Recent advances in antitubercular natural products European Journal of Medicinal Chemistry 49 2012 1 23
30. P. de, G.K. Yoya, P. Constant, F. Bedos-Belval, H. Duran, N. Saffon, M. Daffe, and M. Baltas Design, synthesis and biological evaluation of new cinnamic derivatives as antituberculosis agents Journal of Medicinal Chemistry 54 2011 1449 1461
31. I.Y. Lee, T.D. Gruber, A. Samuels, M. Yun, B. Nam, M. Kang, K. Crowley, B. Winterroth, H.I. Boshoff, and C. Berry Structure-activity relationship of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling Bioorganic & Medicinal Chemistry 21 2013 114 126
32. R. Villar, E. Vicente, B. Solano, S. Perez-Silanes, I. Aldana, J.A. Maddry, A.J. Lenaerts, S.G. Franzblau, S.-H. Cho, A. Monge, and R.C. Goldman Invitro and invivo antimycobacterial activities of ketone and amide derivatives of quinoxaline 1,4-di-N-oxide Journal of Antimicrobial Chemotherapy 62 2008 547 554
33. E. Chew, A.A. Nagle, Y. Zhang, S. Scarmagnani, P. Palaniappan, T.D. Bradshaw, A. Holmgren, and A.D. Westwell Cinnamaldehydes inhibits thioredoxin reductase and induce Nrf2: potential candidates for cancer therapy and chemoprevention Free Radical Biology & Medicine 48 2010 98 111
34. A.B. Alloum, K. Bougrin, and M. Soufiaoui Synthèse chimio sélective des benzimidazoles sur silice traitée par le chlorure du thionyle Tetrahedron Letters 44 2003 5935 5937 (Pubitemid 36829242)
35. S.G. Franzblau, R.S. Witzig, J.C. McLaughlin, P. Torres, G. Madico, A. Hernandez, M.T. Degnan, M.B. Cook, V.K. Quenzer, R.M. Ferguson, and R.H. Gilman Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar blue assay Journal of Clinical Microbiology 36 1998 362 366 (Pubitemid 28060296)
36. A. Doyle, and J.B. Griffiths Cell and Tissue Culture for Medical Research first ed. 2000 John Wiley and Sons Ltd 409