Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 6, 2013, Pages 1255-1260

  Abdul Rahim, Aisyah Saad ^a   Muhamad Salhimi, Salizawati ^a   Arumugam, Natarajan ^a   Pin, Lim Chung ^a   Yee, Ng Shy ^a   Muttiah, Nithya Niranjini ^a   Keat, Wong Boon ^a   Abd Hamid, Shafida ^b   Osman, Hasnah ^c   Mat, Ishak B ^c  

^a SCHOOL OF PHARMACEUTICAL SCIENCES   (Malaysia)

^b SCHOOL OF PHYSICS   (Malaysia)

^c ADVANCED MEDICAL AND DENTAL INSTITUTE   (Malaysia)

Author keywords

2 Arylbenzimidazole; Antiproliferative activity; Breast cancer; Microwave synthesis; MTS assay

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; SEC 2 ARYLBENZIMIDAZOLE DERIVATIVE; TERT 2 ARYLBENZIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MELTING POINT; MICROWAVE RADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MCF-7 CELLS; MICROWAVES; MOLECULAR STRUCTURE; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84887464776     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2012.729828     Document Type: Article

References (38)

1. World Health Organisation -Breast Cancer: Prevention and Control. Available at http://www.who.int/ cancer/detection/breastcancer/ en/. Accessed 23 June 2012
2. Varmus H. The new era in cancer research. Science. 2006;312:1162-1165
3. Rosen ST. Cancer chemoprevention. Bergan RC, ed. New York: Academic Publisher; 2001:137-154
4. Jordan VC. Chemoprevention of breast cancer with selective oestrogen-receptor modulators. Nat Rev Cancer 2007;7:46-53
5. Clarke R, Skaar TC, Bouker KB, Davis N, Lee YR, Welch JN et al. Molecular and pharmacological aspects of antiestrogen resistance. J Steroid Biochem Mol Biol 2001;76:71-84
6. Harrison MR, Holen KD, Liu G. Beyond taxanes: A review of novel agents that target mitotic tubulin and microtubules, kinases, and kinesins. Clin Adv Hematol Oncol 2009;7:54-64
7. Komlodi-Pasztor E, Sackett DL, Fojo AT. Inhibitors targeting mitosis: Tales of how great drugs against a promising target were brought down by a flawed rationale. Clin Cancer Res 2012;18:51-63
8. Green KA, Carroll JS. Oestrogen-receptor-mediated transcription and the influence of co-factors and chromatin state. Nat Rev Cancer 2007;7:713-722
9. Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL et al. Methods for drug discovery: Development of potent, selective, orally effective cholecystokinin antagonists. J Med Chem 1988;31:2235-2246
10. Nicolaou KC, Pfefferkorn JA, Roecker AJ, Cao GQ, Barluenga S, Mitchell HJ. Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans. J Am Chem Soc 2000;122:9939-9953
11. Dettmann S, Szymanowitz K, Wellner A, Schiedel A, Müller CE, Gust R. 2-phenyl-1-[4-(2-piperidine-1-yl-ethoxy)benzyl]-1H-benzimidazoles as ligands for the estrogen receptor: Synthesis and pharmacological evaluation. Bioorg Med Chem 2010;18:4905-4916
12. Bradshaw TD, Stevens MF, Westwell AD. The discovery of the potent and selective antitumour agent 2-(4-Amino-3-methylphenyl) benzothiazole (DF 203) and related compounds. Curr Med Chem 2001;8:203-210
13. Shi DF, Bradshaw TD, Wrigley S, McCall CJ, Lelieveld P, Fichtner I et al. Antitumor benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl) benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J Med Chem 1996;39:3375-3384
14. Romero-Castro A, León-Rivera I, Avila-Rojas LC, Navarrete-Vázquez G, Nieto-Rodríguez A. Synthesis and preliminary evaluation of selected 2-Aryl-5(6)-nitro-1H-benzimidazole derivatives as potential anticancer agents. Arch Pharm Res 2011;34:181-189
15. Abonia R, Cortés E, Insuasty B, Quiroga J, Nogueras M, Cobo J. Synthesis of novel 1,2,5-Trisubstituted benzimidazoles as potential antitumor agents. Eur J Med Chem 2011;46:4062-4070
16. Spasov A, Yozhitsa I, Bugaeva L, Anisimova V. Benzimidazole derivatives: Spectrum of pharmacological activity and toxicological properties (a review). Pharm Chem J 1999;33:232-243
17. Roth T, Morningstar ML, Boyer PL, Hughes SH, Buckheit RW Jr, Michejda CJ. Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Arylsubstituted benzimidazoles. J Med Chem 1997;40:4199-4207
18. Zhu Z, Lippa B, Drach JC, Townsend LB. Design, synthesis, and biological evaluation of tricyclic nucleosides (dimensional probes) as analogues of certain antiviral polyhalogenated benzimidazole ribonucleosides. J Med Chem 2000;43:2430-2437
19. Keurulainen L, Salin O, Siiskonen A, Kern JM, Alvesalo J, Kiuru P et al. Design and synthesis of 2-Arylbenzimidazoles and evaluation of their inhibitory effect against Chlamydia pneumoniae. J Med Chem 2010;53:7664-7674
20. Kim JS, Gatto B, Yu C, Liu A, Liu LF, LaVoie EJ. Substituted 2,5'-Bi-1H-benzimidazoles: Topoisomerase I inhibition and cytotoxicity. J Med Chem 1996;39:992-998
21. Kohara Y, Kubo K, Imamiya E, Wada T, Inada Y, Naka T. Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres. J Med Chem 1996;39:5228-5235
22. Thimmegowda NR, Nanjunda Swamy S, Kumar CS, Kumar YC, Chandrappa S, Yip GW et al. Synthesis, characterization and evaluation of benzimidazole derivative and its precursors as inhibitors of MDA-MB-231 human breast cancer cell proliferation. Bioorg Med Chem Lett 2008;18:432-435
23. Kadri H, Matthews CS, Bradshaw TD, Stevens MF, Westwell AD. Synthesis and antitumour evaluation of novel 2-phenylbenzimidazoles. J Enzyme Inhib Med Chem 2008;23:641-647
24. Camacho J, Barazarte A, Gamboa N, Rodrigues J, Rojas R, Vaisberg A et al. Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents. Bioorg Med Chem 2011;19:2023-2029
25. Starcevic K, Kralj M, Ester K, Sabol I, Grce M, Pavelic K et al. Synthesis, antiviral and antitumor activity of 2-substituted-5-Amidino- benzimidazoles. Bioorg Med Chem 2007;15:4419-4426
26. Narendra Babu SN, Abdul Rahim AS, Osman H, Razak IA, Fun HK. Ethyl 4-fluoro-3-nitro-benzoate. Acta Crystallogr Sect E Struct Rep Online 2009;65:o556
27. Arumugam N, Abdul Rahim AS, Abd Hamid S, Rosli MM, Fun HK. Ethyl 3-Amino-4-[(2-hydroxyethyl)-Amino]benzoate. Acta Crystallogr Sect E Struct Rep Online 2010;66:o2141
28. Yet L. Progress in Heterocyclic Chemistry. Gribble GW, Joule JA, eds. Oxford: Elsevier; 2011:231-266
29. Wright JB. The Chemistry of the Benzimidazoles. Chem Rev. 1951;48:397-541
30. Gogoi P, Konwar D. An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water. Tetrahedron Lett. 2006;47:79-82
31. Navarrete-Vázquez G, Moreno-Diaz H, Aguirre-Crespo F, León-Rivera I, Villalobos-Molina R, Muñoz-Muñiz O et al. Design, microwave-Assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres. Bioorg Med Chem Lett 2006;16:4169-4173
32. Lin S, Yang L. A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett 2005;46(25):4315-4319
33. Abonía R, Castillo J, Cuervo P, Insuasty B, Quiroga J, ortã z A, et al. A Simple One-Pot Synthesis of New Imidazol-2-yl-1 H-quinolin-2-ones from the Direct Reaction of 2-Chloroquinolin-3-carbaldehyde with Aromatic o-Diamines. Eur J Org Chem 2010;2:317-325
34. Refaat HM. Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives. Eur J Med Chem 2010;45:2949-2956
35. Ramla MM, Omar MA, El-Khamry AM, El-Diwani HI. Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles. Bioorg Med Chem 2006;14: 7324-7332
36. Elzahabi HS. Synthesis, characterization of some benzazoles bearing pyridine moiety: Search for novel anticancer agents. Eur J Med Chem 2011;46:4025-4034
37. Rashid M, Husain A, Mishra R. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents Eur. J. Med. Chem. 2012;1-38
38. Shaharyar M, Abdullah MM, Bakht MA, Majeed J. Pyrazoline bearing benzimidazoles: Search for anticancer agent. Eur J Med Chem 2010;45:114-119