Synthesis and preliminary evaluation of selected 2-aryl-5(6)-nitro- 1H-benzimidazole derivatives as potential anticancer agents

Archives of Pharmacal Research

Volumn 34, Issue 2, 2011, Pages 181-189

  Romero Castro, Aurelio ^a   León Rivera, Ismael ^b   Ávila Rojas, Laura Citlalli ^a   Navarrete Vázquez, Gabriel ^a   Nieto Rodríguez, Alejandro ^a  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MORELOS   (Mexico)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

Anticancer; Benzimidazole; Cytotoxicity; Nitrocompounds; PARP

Indexed keywords

2 (3,5 DINITROPHENYL) 5(6) NITRO 1H BENZIMIDAZOLE; 2 (4 CHLORO 3 NITROPHENYL) 5(6) NITRO 1H BENZIMIDAZOLE; 2 ARYL 5(6) NITRO1H BENZIMIDAZOLE DERIVATIVE; 3 AMINOBENZAMIDE; 5(6) NITRO 2 (2 NITROPHENYL) 1H BENZIMIDAZOLE; 5(6) NITRO 2 (3 NITROPHENYL) 1H BENZIMIDAZOLE; 5(6) NITRO 2 (4 NITROPHENYL) 1H BENZIMIDAZOLE; ANTINEOPLASTIC AGENT; CARBOPLATIN; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL ASSAY; CELL CYCLE ARREST; CELL CYCLE S PHASE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZAMIDES; BENZIMIDAZOLES; CELL CYCLE; CELL LINE; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; MOLECULAR TARGETED THERAPY; NITRO COMPOUNDS; NITROBENZENES; POLY(ADP-RIBOSE) POLYMERASES;

EID: 79953293187     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-011-0201-5     Document Type: Article

References (20)

1. Ashworth, A., A synthetic lethal therapeutic approach: poly (ADP) ribose polymerase inhibitors for the treatment of cancers deficient in DNA double-strand break repair. J. Clin. Oncol., 26, 3785-3790 (2008).
2. Bielawski, K., Bielawska, A., and Wolczynski, S., Synthesis, DNA-binding activity and cytotoxicity of carbamate derivatives of Hoechst 33258 in breast cancer MCF-7 cells. Biol. Pharm. Bull., 25, 916-919 (2002).
3. Cliby, W. A., Lewis, K. A., Lilly, K. K., and Kaufmann, S. H., S phase and G2 arrests induced by topoisomerase I poisons are dependent on ATR kinase function. J. Biol. Chem., 277, 1599-1606 (2002).
4. Curtin, N. J., Wang, L. Z., Yiakouvaki, A., Kyle, S., Arris, C. A., Canan-Koch, S., Webber, S. E., Durkacz, B. W., Calvert, H. A., Hostomsky, Z., and Newell, D. R., Novel poly(ADP-ribose) polymerase-1 inhibitor, AG14361, restores sensitivity to temozolomide in mismatch repair-deficient cells. J. Clin. Cancer Res., 10, 881-889 (2004).
5. Ghodousi, A., Huang, X., Cheng, Z., and Skibo, E., Pyrrolobenzimidazoles linked to heterocycles and peptides. Design of DNA base pair specific phosphate hydrolyzing agents and novel cytotoxic agents. J. Med. Chem., 47, 90-100 (2004).
6. Helsby, N. A., Wheeler, S. J., Pruijn, F. B., Palmer, B. D., Yang, S., Denny, W. A., and Wilson, W. R., Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: distinct mechanisms of bioreductive activation. Chem. Res. Toxicol., 16, 469-478 (2003).
7. Jagtap, P. and Szabó, C., Poly (ADP-ribose) polymerase and the therapeutic effects of its inhibitors. Nat. Rev. Drug Discov., 4, 421-440 (2005).
8. Karali. N., Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives. Eur. J. Med. Chem., 37, 909-918 (2002).
9. Kim, J. S., Yu. C., Liu, A., Liu, L. F., and LaVoie, E. J., Terbenzimidazoles: influence of 2″-, 4-, and 5-substituents on cytotoxicity and relative potency as topoisomerase I poisons. J. Med. Chem., 40, 2818-2824 (1997).
10. Min, J. K., Kim, H. M., Kim, D.-D., and Kim, J. S., The effect of 5-substitution on the cytotoxicity of 2-(p-methoxyphenyl)-1H-benzimidazoles in human cancer cell lines. Key Eng. Mater. Vols., 23, 277-279 (2005).
11. Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., and Vistica, D., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst., 83, 757 (1991).
12. Moree, W. J., Goldman, P., Demaggio, A. J., Christenson, E., Herendeen, D., Eksterowicz, J., Kesicki, E. A., McElligott, D. L., and Beaton, G., Identification of ring-fused pyrazolo pyridin-2-ones as novel poly(ADP-ribose)polymerase-1 inhibitors. Bioorg. Med. Chem. Lett., 18, 5126-5129 (2008).
13. Navarrete-Vázquez, G., Moreno-Diaz, H., Aguirre-Crespo, F., León-Rivera, I., Villalobos-Molina, R., Muñoz-Muñiz, O., and Estrada-Soto, S., Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1Hbenzimidazole derivatives as constrained stilbene bioisosteres. Bioorg. Med. Chem. Lett., 16, 4169-4173 (2006).
14. Özden, S., Atabey, D., Yildiz, S., and Göker, H., Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups. Bioorg. Med. Chem., 13, 1587-1597 (2005).
15. Ramla, M. M., Omar, M. A., El-Khamry, A. M., and El-Diwani, H. I., Synthesis and antitumor activity of 1-substituted-2-methyl-5- nitrobenzimidazoles. Bioorg. Med. Chem., 14, 7324-7332 (2006).
16. Stepanchikova, A. V., Lagunini, A. A., Filimonov, D. A., and Poroikov, V. V., Prediction of biological activity spectra for substances: evaluation on the diverse sets of drug-like structures. Curr. Med. Chem., 10, 225-233 (2003).
17. Tentori, L. and Graziani, G., Chemopotentiation by PARP inhibitors in cancer therapy. Pharmacol. Res., 52, 25-33 (2005).
18. White, A. W., Curtin, N. J., Eastman, B. W., Golding, B. T., Hostomsky, Z., Kyle, S., Li, J., Maegley, K. A., Skalitzky, D. J., Webber, S. E., Yu, X. H., and Griffin, R. J., Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors. Bioorg. Med. Chem. Lett., 14, 2433-2437 (2004).
19. Yun-Fei, L., Gui-Feng, W., Pei-Lan, H., Wei-Gang, H., Feng-Hua, Z., He-Yong, G., Wei, T., Yu, L., Chun-Lan, F., Li-Ping, S., Yu-Dan, R., Wei, L., and Jian-Ping, Z., Synthesis and anti-hepatitis B virus activity of novel benzimidazole derivatives. J. Med. Chem., 49, 4790-4794 (2006).
20. Zhu, G. D., Gandhi, V. B., Gong, J., Thomas, S., Luo, Y., Liu, X., Shi, Y., Klinghofer, V., Johnson, E. F., Frost, D., Donawho, C., Jarvis, K., Bouska, J., Marsh, K. C., Rosenberg, S. H., Giranda, V. L., and Penning, T. D., Synthesis and SAR of novel, potent and orally bioavailable benzimidazole inhibitors of poly(ADP-ribose) polymerase (PARP) with a quaternary methylene-amino substituent. Bioorg. Med. Chem. Lett., 18, 14, 3955-3958 (2008).