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Research Article

Synthesis and anticancer activity of some 1,2,3-trisubstituted pyrazinobenzimidazole derivatives

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Pages 811-822 | Received 08 Jul 2013, Accepted 14 Oct 2013, Published online: 24 Jan 2014

References

  • Li X, Weng L, Gao X, et al. Antiproliferative and apoptotic sesquiterpene lactones from Carpesium faberi. Bioorg Med Chem Lett 2011;21:366–72
  • Siriwana D, Naruse T, Tamura H. Effect of epoxides and α-methylene-γ-lactone skeleton of sesquiterpenes from yacon (Smallanthus sonchifolius) leaves on caspase-dependent apoptosis and NF-κB inhibition in human cercival cancer cells. Fitoterapia 2011;82:1093–101
  • Ma G, Chong L, Li Z, et al. Anticancer activities of sesquiterpene lactones from Cyathocline purpurea in vitro. Cancer Chemother Pharmacol 2009;64:143–52
  • Basarić N, Cindro N, Bobinac D, et al. Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity. Photochem Photobiol Sci 2011;10:1910–25
  • Zhang Y, Tu Y, Gao X, et al. Strong inhibition of celastrol towards UDP-glucuronosyl transferase (UGT) 1A6 and 2B7 indicating potential risk of UGT-based herb-drug interaction. Molecules 2012;17:6832–9
  • Lee KH, Ibuka T, Kim SH, et al. Antitumor agents. 16. Steroidal .alpha.-methylene-.gamma.-lactones. J Med Chem 1975;18:812–17
  • Hernandez R, Velazquez SM, Suarez E. Synthesis of (+)-8-deoxyvernolepin. J Org Chem 1994;59:6395–403
  • Howie GA, Manni PE, Cassady JM. Synthesis of alkyl-substituted α,β-unsaturated γ-lactones as potential antitumor agents. J Med Chem 1974;17:840–3
  • Kupchan SM, Eakin MA, Thomas AM. Tumor inhibitores. 69. Structure–cytotoxicity relationships among the sesquiterpene lactones. J Med Chem 1971;14:1147–52
  • Rosowsky A, Papathanasopoulos N, Lazarus H, et al. Cysteine scavengers. 2. Synthetic α-methylenebutyrolactones as potential tumor inhibitors. J Med Chem 1974;17:672–6
  • Lin AJ, Cosby LA, Shansky CW, Sartorelli AC. Potential bioreductive alkylating agents. 3. Synthesis and antineoplastic activity of acetoxymethyl and corresponding ethyl carbamate derivatives of benzoquinones. J Med Chem 1974;17:558–61
  • Lin AJ, Pardini RS, Lillis BJ, Sartorelli AC. Potential bioreductive alkylating agents. 4. Inhibition of coenzyme Q enzyme systems by lipoidal benzoquinone and naphthoquinone derivatives. J Med Chem 1974;17:668–72
  • Moore HW. Bioactivation as a model for drug design bioreductive alkylation. Science 1977;197:527–32
  • Lee CH, Skibo EB. Active-site-directed reductive alkylation of xanthine oxidase by imidazo[4,5-g]quaninazoline-4,9-diones functionalized with a leaving group. Biochem 1987;26:7355–62
  • Lemus RH, Lee CH, Skibo EB. Studies of extended quinone methides. Synthesis and physical studies of purine-like monofunctional and bifunctional imidazo[4,5-g]quinazoline reductive alkylating agents. J Org Chem 1989;54:3611–18
  • Lemus RH, Skibo EB. Studies of extended quinone methides. Design of reductive alkylating agents based on the quinazoline ring system. J Org Chem 1988;53:6099–105
  • Skibo EB. Studies of extended quinone methides. The hydrolysis mechanism of 1-methyl-2-(bromomethyl)-4,7-dihydroxybenzimidazole. J Org Chem 1986;51:522–7
  • Pratt WB, Ruddon RW, Ensminger WD. (1994). The anticancer drugs. Part 2. New York: Oxford University Press
  • Rajski SC, Williams RM. DNA cross-linking agents as antitumor drugs. Chem Rev 1998;98:2723–95
  • Doria F, Nadai M, Folini M, et al. Hybrid ligand–alkylating agents targeting telomeric G-quadruplex structures. Org Biomol Chem 2012;10:2798–806
  • Avendaño C, Menendez JC. Medicinal chemistry of anticancer drugs. Hungary: Elsevier; 2008. Chapter 6
  • Demirayak S, Abu Mohsen U. Anticancer and anti-HIV activities of some pyrido/pyrazino-benzimidazole derivatives. Acta Pharm Turc 1998;40:9–12
  • Demirayak S, Mohsen UA, Karaburun AC. Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. Eur J Med Chem 2002;37:255–60
  • Demirayak S, Kayagil I, Yurttas L. Microwave supported synthesis of some novel 1,3-diarylpyrazino[1,2-a]benzimidazole derivatives and investigation of their anticancer activities. Eur J Med Chem 2011;46:411–16
  • Siegart WR, Day AR. Metabolit analogs. VII. Preparation of some benzimidazolyl analogs of ethyl pteroylglutamate. J Am Chem Soc 1957;79:4391–4
  • Cheeseman GW. 2-Acetylbenzimidazole. J Chem Soc 1964;4645–6
  • Demirayak S, Güven K. Synthesis of some pyrido- and pyrazino-benzimidazole derivatives and their antifungal activity. Pharmazie 1995;50:527–9
  • Boyd MR. Status of the NCI preclinical antitumor drug discovery screen. Princip Prac Oncol 1989;3:1–12
  • Monks A, Scudiero D, Skehan P, et al. Feasibility of a high-flux anticancer drug screen using a divers panel of cultured human tumor cell. J Natl Cancer Inst 1991;83:757–66
  • Boyd MR, Paull KD. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev Res 1995;34:91–109
  • Husain A, Rashid M, Shaharyar M, et al. Benzimidazole clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: new anticancer agents. Eur J Med Chem 2013;62:785–98
  • Kode N, Chen L, Murthy D, et al. New bis-N9-(methylphenylmethyl)purine derivatives: synthesis and antitumor activity. Eur J Med Chem 2007;42:327–33

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