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Research Article

Synthesis and anticancer activity evaluation of N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives containing (benz)azole moiety

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Pages 175-184 | Received 11 Sep 2012, Accepted 31 Dec 2012, Published online: 07 Feb 2013

References

  • Liott LA, Steeg PS, Steller-Stevenson WG. Cancer metastasis and angiogenesis: an imbalance of positive and negative regulation. Cell 1991;64:327–36
  • Mignatti P, Rifkin DB. Biology and biochemistry of proteinases in tumor invasion. Physiol Rev 1993;73:161–5
  • Dudkin VY, Wang, C, Arrington KL, et al. Pyridyl aminothiazoles as potent Chk1 inhibitors: optimization of cellular activity. Bioorg Med Chem 2012;12:2613–9
  • Karikas GA, Schulpis KH, Reclos G, Kokotos G. Measurement of molecular interaction of aspartame and its metabolites with DNA. Clin Biochem 1998;31:405–7
  • Filosa R, Pedut A, Caprariis P, et al. Synthesis and antiproliferative properties of N3/8-disubstituted 3,8-diazabicyclo[3.2.1]octane analogues of 3,8-bis[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl-piperazine. Eur J Med Chem 2007;42:293–306
  • Earle MF, Glazer RI. Activity and metabolism of 2-β-d-Ribofuranosylthiazole-4 carboxamide in human lymphoid tumor cells in culture. Cancer Res 1983;43:133–7
  • Tricot GJ, Jayaram NH, Weber G, Hoffman RI. Tiazofurin: biological effects and clinical uses. Int J Cell Cloning 1990;8:161–70
  • Tricot GJ, Jayaram NH, Lapis E, et al. Biochemically directed therapy of leukemia with tiazofurin, a selective blocker of inosine 5'-phosphate dehydrogenase activity. Cancer Res 1989;49:3696–701
  • Zimmer C, Wahnert U. Nonintercalating DNA-binding ligands: specificity of the interaction and their use as tools in biophysical, biochemical and biological investigations of the genetic material. Prog Biophys Mol Biol 1986;47:31–112
  • Umezawa H, Suhara Y, Taketa T, Maeda K. Purification of bleomycins. J Antibiot 1966;19:210–5
  • Umezawa H, Takeuchi S, Hori T, et al. Studies on the mechanism of antitumor effect of bleomycin of squamous cell carcinoma. J Antibiot 1972;25:409–20
  • Plouvier B, Houssin R, Baily C, Henichart J. Synthesis and DNA-binding study of a thiazole-containing analog of netropsin. J Heterocyclic Chem 1989;26:1643–7
  • Lu Y, Li CM., Wang Z, et al. Discovery of 4-substitutedmethoxybenzoyl-aryl-thiazole as novel anticancer agents: synthesis, biological evaluation and structure–activity relationships. J Med Chem 2009;52:1701–11
  • Garuti L, Roberti M, Pession A, et al. Synthesis and antiproliferative activity of some thiazolylbenzimidazole-4,7-diones. Bioorg Med Chem Lett 2001;11:3147–9
  • Bolos CA, Papazisi KT, Kortsaris AH, Voyatzi S. Antiproliferative activity of mixed-ligand dien-Cu(II) complexes with thiazole, thiazoline and imidazole derivatives. J Inorg Biochem 2002;88:25–36
  • Yalowitz JA, Pankiewicz K, Patterson SE, Jayaram HN. Cytotoxicity and cellular differentiation activity of methylenebis(phosphonate) analogs of tiazofurin and mycophenolic acid adenine dinucleotide in human cancer cell lines. Cancer Lett 2002;181:31–8
  • Li Z, Yang Q, Qian X. Novel thiazonaphthalimides as efficient antitumor and DNA photocleaving agents: effects of intercalation, side chains, and substituent groups. Bioorg Med Chem 2005;13:4864–70
  • Cejudo R, Alzuet G, Gonzalez-Alvarez M, Garcia-Gimenez JL. DNA cleavage reaction induced by dimeric copper(II) complexes of N-substituted thiazole sulphonamides. J Inorg Biochem 2006;100:70–9
  • Aliabadi A, Shamsa F, Ostad SN, et al. Synthesis and biological evaluation of 2-phenylthiazole-4-carboxamide derivatives as anticancer agents. Eur J Med Chem 2010;45:5384–9
  • Fallah-Tafti A, Foroumadi A, Tiwari R, et al. Thiazolyl N-benzyl-substituted acetamide derivatives: synthesis, Src kinase inhibitory and anticancer activities. Eur J Med Chem 2011;46:4853–8
  • Gan L, Fang B, Zhou C. Synthesis of azole-containing piperazine derivatives and evaluation of their antibacterial, antifungal and cytotoxic activities. Bull Korean Chem Soc 2010;31:3684–92
  • Rodriguez RJ, Acosta DJ. Comparison of ketoconazole- and fluconazole-induced hepatotoxicity in a primary culture system of rat hepatocytes. Toxicology 1995;96:83–92
  • Boiani M, Gonzalez M. Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini-Rev Med Chem 2005;5:409–24
  • Ramla MM, Omar MA, Tokuda H, El-Diwani H. Synthesis and inhibitory activity of new benzimidazole derivatives against Burkitt’s lymphoma promotion. Bioorg Med Chem 2007;15:6489–96
  • Mann J, Baron A, Opoku-Boahen Y, et al. A new class of symmetric bis-benzimidazole-based DNA minor groove binding agents. J Med Chem 2001;44:138–44
  • Ören İ, Temiz Ö, Yalcın İ, et al. Synthesis and antimicrobial activity of some novel 2,5- and/or 6-substituted benzoxazole and benzimidazole derivatives. Eur J Pharm Sci 1999;7:153–60
  • Hisano T, Ichikawa M, Tsumoto K, Tasaki M. Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities. Chem Pharm Bull 1982;30:2996–3004
  • Nayyar A, Jain R. Recent advances in new structural classes of anti-tuberculosis agents. Curr Med Chem 2005;12:1873–86
  • Jimonet P, Audiau F, Barreau M, et al. Riluzole series. Synthesis and in vivo “antiglutamate” activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines. J Med Chem 1999;42:2828–43
  • Wood PM, Lawrence LW, Thomas MP, et al. Aromatase and dual aromatase-steroid sulfatase inhibitors from the Letrozole and Vorozole templates. Chem Med Chem 2011;6:1423–38
  • Trigg ME, Flanigan-Minnick A. Mechanisms of action of commonly used drugs to treat cancer. Commun Oncol 2011;8:358–69
  • Ojha H, Murari BM, Anand S, et al. Interaction of DNA minor groove binder Hoechst 33258 with bovine serum albumin. Chem Pharm Bull 2009;57:481–6
  • Kumar D, Jacob MR, Reynolds MB, Kerwina SM. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Bioorg Med Chem 2002;10:3997–4004
  • Fichtner I, Monks A, Hose C, et al. The experimental antitumor agents Phortress and Doxorubicin are equiactive against human-derived breast carcinoma xenograft models. Breast Canc Res Treat 2004;87:97–107
  • Özkay Y, Işıkdağ İ, İncesu Z, Akalın 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;45:3320–8
  • Peet NP, Sunder S, Barbuch RJ, et al. Reinvestigation of a 5H-dibenzo[d,h][1,3,6]triazonine synthesis. J Het Chem 1989;26:1611–7
  • Xing R, Pan L, Wen X, et al. A practical and efficient procedure for the α-bromination of arylethanones. J Chinese Pharm Sci 2010;19:400–2
  • Yurchenko RI, Malitskaya VP. Syntheses based on p-azido-ω-haloacetophenones. Z Organich Khim 1977;1:1980–7
  • Mossmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63
  • Wang GW, Klein JB, Kang YJ. Metallothionein inhibits doxorubicin-induced mitochondrial cytochrome C release and caspase-3 activation in cardiomyocytes. J Pharmacol Exp Ther 2001;298:461–8
  • Cotter TG, Martin SJ. Techniques in apoptosis (a user’s guide). London: Portland Press; 1996:107–20

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