Synthesis and structure-activity relationships of novel furazan-3,4-diamide analogs as potent anti-cancer agents

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 1148-1152

  Li, Wen Shan ^a   More, Shivaji V ^a,b   Wang, Chie Hong ^a   Jen, Ya Ching ^a   Yao, Ching Fa ^b   Wang, Tein Fu ^a   Hung, Chin Chun ^c   Jao, Shu Chuan ^c  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^c INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

Anti cancer agents; Drug discovery; Structure activity relationship; Synthesis

Indexed keywords

3,4 DIAMINOFURAZAN; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; BENZOFURAZAN DERIVATIVE; FURAZAN 3,4 DIAMIDE; FURAZAN DERIVATIVE; UNCLASSIFIED DRUG; DIAMIDE; FURAN DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL GROWTH; CELL PROLIFERATION; CONTROLLED STUDY; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; ELECTRON; HUMAN; HUMAN CELL; RING OPENING; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; TUMOR CELL; ANALOGS AND DERIVATIVES; COMPARATIVE STUDY; DRUG EFFECTS; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DIAMIDE; FURANS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 74049164892     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.017     Document Type: Article

References (26)

1. Newman D.J., Cragg G.M., and Snader K.M. J. Nat. Prod. 66 (2003) 1022
2. Koehn F.E., and Carter G.T. Nat. Rev. Drug Disc. 4 (2005) 206
3. Haustedt L.O., Mang C., Siems K., and Schiewe H. Curr. Opin. Drug Discov. Devel. 9 (2006) 445
4. Baranczewski P., Stańczak A., Kautiainen A., Sandin P., and Edlund P.O. Pharmacol. Rep. 58 (2006) 341
5. Harvey A.L. Drug Discovery Today 13 (2008) 894
6. Li J.W., and Vederas J.C. Science 325 (2009) 161
7. Cragg G.M., Grothaus P.G., and Newman D.J. Chem. Rev. 109 (2009) 3012
8. Gross H. Curr. Opin. Drug Discov. Devel. 12 (2009) 207
9. Terracciano S., Aquino M., Rodriquez M., Monti M.C., Casapullo A., Riccio R., and Gomez-Paloma L. Curr. Med. Chem. 13 (2006) 1947
10. Barthomeuf C., Bourguet-Kondracki M.L., and Kornprobst J.M. Anticancer Agents Med. Chem. 8 (2008) 886
11. Schuffenhauer A., Ruedisser S., Marzinzik A.L., Jahnke W., Blommers M., Selzer P., and Jacoby E. Curr. Top Med. Chem. 5 (2005) 751
12. Janssens J.C., De Keersmaecker S.C., De Vos D.E., and Vanderleyden J. Curr. Med. Chem. 15 (2008) 2144
13. Vulpetti A., Hommel U., Landrum G., Lewis R., and Dalvit C. J. Am. Chem. Soc. 131 (2009) 12949
14. Cerecetto H., and Porcal W. Mini Rev. Med. Chem. 5 (2005) 57
15. Medana C., Di Stilo A., Visentin S., Fruttero R., Gasco A., Ghigo D., and Bosia A. Pharm. Res. 16 (1999) 956
16. Buonsanti M.F., Bertinaria M., Stilo A.D., Cena C., Fruttero R., and Gasco A. J. Med. Chem. 50 (2007) 5003
17. Turnbull C.M., Cena C., Fruttero R., Gasco A., Rossi A.G., and Megson I.L. Br. J. Pharmacol. 148 (2006) 517
18. Cena C., Lolli M.L., Lazzarato L., Guaita E., Morini G., Coruzzi G., McElroy S.P., Megson I.L., Fruttero R., and Gasco A. J. Med. Chem. 46 (2003) 747
19. Beebe X., Nilius A.M., Merta P.J., Soni N.B., Bui M.H., Wagner R., and Beutel B.A. Bioorg. Med. Chem. Lett. 13 (2003) 3133
20. LoGrasso P.V., and Feng Y. Curr. Top Med. Chem. 9 (2009) 704
21. Visentin S., Rolando B., Di Stilo A., Fruttero R., Novara M., Carbone E., Roussel C., Vanthuyne N., and Gasco A. J. Med. Chem. 47 (2004) 2688
22. Lolli M.L., Cena C., Medana C., Lazzarato L., Morini G., Coruzzi G., Manarini S., Fruttero R., and Gasco A. J. Med. Chem. 44 (2001) 3463
23. Sorba G., Gasco A., and Orsetti M. Arch. Pharm. 322 (1989) 579
24. Fernández E., García-Ochoa S., Huss S., Mallo A., Bueno J.M., Micheli F., Paio A., Piga E., and Zarantonello P. Tetrahedron Lett. 43 (2002) 4741
25. 2, 20% EtOAc/hexane) to afford compound 12 (262 mg, 85%).
26. 2, 20% EtOAc/hexane) to afford compound 27 (275 mg, 80%).