New potential inhibitors of DNA topoisomerase. Part II: Design and synthesis of α-lapachone derivatives under microwave irradiation

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 3, 2009, Pages 828-830

  Wei, Ping ^a   Zhang, Xiaohong ^b   Tu, Shujiang ^b   Yan, Shu ^b   Ying, Hanjie ^a   Ouyang, Pingkai ^a  

^a NANJING TECH UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Lapachone; DNA topoisomerase II; Microwave irradiation; Potential inhibitors

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA LAPACHONE DERIVATIVE; DNA TOPOISOMERASE INHIBITOR; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; MICROWAVE IRRADIATION; QUANTUM YIELD;

ANTINEOPLASTIC AGENTS; CHEMISTRY, PHARMACEUTICAL; DNA TOPOISOMERASES, TYPE I; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MICROWAVES; MODELS, BIOLOGICAL; MODELS, CHEMICAL; NEOPLASMS; SOLVENTS; TEMPERATURE; TIME FACTORS;

EID: 58549102691     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.12.006     Document Type: Article

References (28)

1. WHO Cancer. Available from: , .
2. Driscoll J.S., Hazard Jr. G.F., Wood Jr. H.B., and Goldin A. Cancer Chemother. Rep. 2 4 (1974) 1-27
3. Liu K.K.-C., Li J., and Sakya S. Mini-Rev. Med. Chem. 4 (2004) 1105
4. Thomson R.H. Naturally Occurring Quinones IV: Recent Advances (1997), Blackie Academic and Professional, London
5. Thomson R.H. Naturally Occurring Quinones III: Recent Advances (1987), Chapman and Hall, London
6. Hudson A.T. Spec. Publ. R. Soc. Chem. 65 (1988) 266
7. Elleff S., Kennaway N.G., Buis N.R.M., Darley-Usmar U.M., Capaldi R.A., Bank W.J., and Chance B. Proc. Natl. Acad. Sci. USA 81 (1984) 3529
8. Powis G. Pharmacol. Ther. 35 (1987) 57
9. Ravelo A., Estévez-Braun A., Chávez-Orellana H., Pérez-Sacau E., and Mesa-Silverio D. Curr. Top. Med. Chem 4 (2004) 241
10. Guiraud P., Steiman R., Campos-Takaki G.M., Seigle-Murandi F., and Simeon de Buochberg M.S. Planta Med. 60 (1994) 373
11. de Andrade-Neto V.F., Goulart M.O.F., da Silva Filho J.F., da Silva M.J., Pinto M.C.F.R., Pinto A.V., Zalis M.G., Carvalho L.H., and Krettli A.U. Bioorg. Med. Chem. Lett. 14 (2004) 1145
12. Pérez-Sacau E., Estévez-Braun A., Ravelo A.G., Gutiérrez D., and Giménez A. Chem. Biodiversity 2 (2005) 264
13. Goulart M.O., Zani C.I., Tonholo J., Freitas de Abreu F.C., Oliveira A.B., Raaslan D.S., Starling S., and Chiari E. Bioorg. Med. Chem. Lett. 7 (1997) 2043
14. Ferreira V., Jorqueira A., Souza A., da Silva M., de Souza M., Gouvea R., Rodrigues C., Pinto A., Castro H., Santos D., Araujo H., and Bourguignon S. Bioorg. Med. Chem. 14 (2006) 5459
15. Fujiwara A., Mori T., Lida A., Ueda S., Nomura T., Tokuda H., and Nishino H. J. Nat. Prod. 61 (1998) 629
16. Krishnan P., and Bastow K.F. Biochem. Pharmacol. 60 (2000) 1367
17. Pérez-Sacau E., Estévez-Braun A., Ravelo A.G., Ferro E.A., Tokuda H., Mukainaka T., and Nishino H. Bioorg. Med. Chem. 11 (2003) 483
18. Suzuki M., Amano M., Choi J., Park H.J., Williams B.W., Ono K., and Song C.W. Radiat. Res. 165 (2006) 525
19. Lee J.I., Choi D.Y., Chung H.S., Seo H.G., Woo H.J., Choi B.T., and Choi Y.H. Exp. Oncol. 28 (2006) 30
20. Woo H.J., Park K.-Y., Rhu C.-H., Lee W.H., Choi B.T., Kim G.Y., Park Y.-M., and Choi Y.H. J. Med. Food 9 (2006) 161
21. Sacau E.P., Esteveg-Braun A., Ravelo A.G., Ferro E.A., Tokuda H., Mukainaka T., and Nishino H. Bioorg. Med. Chem. 11 (2003) 483
22. Evans B.E., Rittle K.E., Bock M.G., Di Pardo R.M., Freindinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S.L., Lotte V.J., Cerino D.J., Chen T.B., Kling P.J., Kimkel K.A., Springer J.P., and Hirshfield J. J. Med. Chem. 31 (1988) 2235
23. Mason J.S., Morize I., Menard P.R., Cheney D.L., Hulme C., and Labandiniere R.F. J. Med. Chem. 42 (1999) 3251
24. Itoigawa M., Ito C., Tan H.T.-W., Okuda M., Tokuda H., Nishino H., and Furukawa H. Cancer Lett. 174 (2001) 135
25. Kapadia G.J., Balasubramanian V., Tokuda H., Konoshima T., Takasaki M., Koyama J., Tagahaya K., and Nishino H. Cancer Lett. 113 (1997) 47
26. Krishnan P., and Bastow K.F. Cancer Chemother. Pharmacol. 47 (2001) 187
27. Krishnan P., and Bastow K.F. Biochem. Pharmacol. 60 (2000) 1367
28. 4: C, 59.55; H, 2.89. Found: C, 59.74; H, 2.92.