Synthesis and anticancer activity of 5,6,8,13-tetrahydro-7H-naphtho[2,3-a][3]-benzazepine-8,13-diones

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• 作者：Weerachai Phutdhawong (1)
  Gedsirin Eksinitkun (2)
  Wanwikar Ruensumran (1)
  Thongchai Taechowisan (3)
  Waya S. Phutdhawong (2)
  
• 关键词：Naphthoquinones ; Aminonaphthoquinones ; Benzazepine ; Anticancer agents
• 刊名：Archives of Pharmacal Research
• 出版年：2012
• 出版时间：May 2012
• 年：2012
• 卷：35
• 期：5
• 页码：769-777
• 全文大小：408KB
• 参考文献：1. Camara, C. A., Pinto, A. C., Vargas, M. D., and Zukerman-Schpector, J., Azepines from the intramolecular Prins cyclization of an aminoderivative of lapachol. / Tetrahedron, 58, 6135-140 (2002). CrossRef
  2. Chaker, L., Pautet, F., and Fillion, H., Studies on the oxidative addition of / N, N-dimethylamine to bromojuglones and bromomethyljuglones. / Chem. Pharm. Bull. (Tokyo), 42, 2238-240 (1994). CrossRef
  3. Kim, J. S., Lee, H. J., Suh, M. E., Choo, H. Y., Lee, S. K., Park, H. J., Kim, C., Park, S. W., and Lee, C. O., Synthesis and cytotoxicity of 1-substituted 2-methyl-1H-imidazo[4, 5-g]phthalazine-4,9-dione derivatives. / Bioorg. Med. Chem., 12, 3683-686 (2004). CrossRef
  4. Kita, Y., Takada, T., Ibaraki, M., Gyoten, M., Mihara, S., Fujita, S., and Tohma, H., An intramolecular cyclization of phenol derivatives bearing aminoquinones using a hypervalent iodine reagent. / J. Org. Chem., 61, 223-27 (1996). CrossRef
  5. Kn?lker, H.-J. and O’sullivan, N., Indoloquinones-3. Palladiumpromoted synthesis of hydroxy substituted 5-cyano-5Hbenzo[b]carbazole-6,11-diones. / Tetrahedron, 50, 10893-0908 (1994). CrossRef
  6. Lee, H. J., Suh, M. E., and Lee, C. O., Synthesis and cytotoxicity evaluation of 2-amino-and 2-hidroxy-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives. / Bioorg. Med. Chem., 11, 1511-519 (2003). CrossRef
  7. Miguel del Corral, J. M., Castro, M. A., Gordaliza, M., Martín, M. L., Gualberto, S. A., Gamito, A. M., Cuevas, C., and San Feliciano, A., Synthesis and cytotoxicity of new aminoterpenylquinones. / Bioorg. Med. Chem., 13, 631-44 (2005). CrossRef
  8. Miguel del Corral, J. M., Castro, M. A., Gordaliza, M., Martín, M. L., Gamito, A. M., Cuevas, C., and Feliciano, A. S., Synthesis and cytotoxicity of new heterocyclic terpenylnaphthoquinones. / Bioorg. Med. Chem., 14, 2816-827 (2006a). CrossRef
  9. Miguel del Corral, J. M., Castro, M. A., Oliveira, A. B., Gualberto, S. A., Cuevas, C., and San Feliciano, A., New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones. / Bioorg. Med. Chem., 14, 7231-240 (2006b). CrossRef
  10. Nimgirawath, S., Udomputtimekakul, P., Taechowisan, T., Wanbanjob, A., and Shen, Y., First total syntheses of (±)-isopiline, (±)-preocoteine, (±)-oureguattidine and (±)-3-methoxynordomesticine and the biological activities of (±)-3-methoxynordomesticine. / Chem Pharm Bull. (Tokyo), 57, 368-76 (2009). CrossRef
  11. Park, B. M., Hong, S. S., Lee, C., Lee, M. S., Kang, S. J., Shin, Y. S., Jung, J. K., Hong, J. T., Kim, Y., Lee, M. K., and Hwang, B. Y., Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide. / Arch. Pharm Res., 33, 381-85 (2010). CrossRef
  12. Phutdhawong, W. S., Ruensamran, W., Phutdhawong, W., and Taechowisan, T., Synthesis of 1,6,7,8-tetrahydro-naphtho[2,3- / d]-azepino[4,5- / b]indole-9,14-diones and their inhibitory effects on pro-inflammatory cytokines. / Bioorg. Med. Chem. Lett., 19, 5753-756 (2009). CrossRef
  13. Ruensamran, W., Microwave-assisted synthesis and antimicrobial activity of heterocyclic naphthoquinones. M.S. Thesis, Department of Chemistry, Silpakorn University, Bangkok, Thailand (2009).
  14. Tandon, V. K., Singh, R. V., and Yadav, D. B., Synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antiviral, antifungal and anticancer agents. / Bioorg. Med. Chem. Lett., 14, 2901-904 (2004). CrossRef
  15. Valderrama, J. A., Leiva, H., Rodríguez, J. A., Theoduloz, C., and Schmeda-Hirshmann, G., Studies on quinones. Part 43: Synthesis and cytotoxic evaluation of polyoxyethylene-containing 1,4-naphthoquinones. / Bioorg. Med. Chem., 16, 3687-693 (2008). CrossRef
  16. Van, T. N. and Kimpe, N. D., Synthesis of 6H-naphtho[2,3- / c] chromene-7,12-diones via palladium-catalyzed intramolecular cyclization of 2-bromo-3-aryloxymethyl-1,4-naphthoquinones. / Tetrahedron, 59, 5941-946 (2003). CrossRef
  17. Yamashita, M., Kaneko, M., Iida, A., Tokuda, H., and Nishimura, K., Stereoselective synthesis and cytotoxicity of a cancer chemopreventive naphthoquinone from / Tabebuia avellanedae. / Bioorg. Med. Chem. Lett., 17, 6417-420 (2007). CrossRef
  
• 作者单位：Weerachai Phutdhawong (1)
  Gedsirin Eksinitkun (2)
  Wanwikar Ruensumran (1)
  Thongchai Taechowisan (3)
  Waya S. Phutdhawong (2)
  
  1. Department of Chemistry, Faculty of Liberal Arts and Science, Kasetsart University, Kampang Saen campus, Nakhon Pathom, 73140, Thailand
  2. Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom, 73000, Thailand
  3. Department of Microbiology, Faculty of Science, Silpakorn University, Nakhon Pathom, 73000, Thailand
  
• ISSN：1976-3786

文摘

A series of naphthoquinones fused benzazepines, 5,6,8,13-tetrahydro-7H-naphtho[2,3-a][3]-benzazepine-8,13-diones, were synthesized and evaluated for their anticancer activity against four cell lines; human breast carcinoma cell line, human cervix carcinoma cell line, human hepatocellular carcinoma cell line and human keratinocyte cell line. The results showed that 5,6,8,13-tetrahydro-2,3,4,9-tetramethoxy-7H-naphtho[2,3-a][3]benzazepine-8,13-dione 4g and 5,6,8,13-tetrahydro-2,3,9-trimethoxy-7H-naphtho[2,3-a][3]benzazepine-8,13-dione 4h have significant cytotoxicity against a hepatocellular carcinoma cell line with IC50 = 3.5 μg/mL and 3.0 μg/mL, respectively.