Synthesis and structure-activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 24, 2009, Pages 8234-8240

  Morita, Hiroshi ^a   Tomizawa, Yuichiro ^a   Deguchi, Jun ^a   Ishikawa, Tokio ^a   Arai, Hiroko ^a   Zaima, Kazumasa ^a   Hosoya, Takahiro ^a   Hirasawa, Yusuke ^a   Matsumoto, Takayuki ^a   Kamata, Katsuo ^a   Ekasari, Wiwied ^b   Widyawaruyanti, Aty ^b   Wahyuni, Tutik Sri ^b   Zaini, Noor Cholies ^b   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

^b AIRLANGGA UNIVERSITY   (Indonesia)

Author keywords

Antimalarial activity; Cassia siamea; Cassiarin A; Nitric oxide; Plasmodium falciparum; SAR; Vasorelaxant activity

Indexed keywords

2,4,5 TRIMETHYLPYRANO[2,3,4 IJ]ISOQUINOLIN 8 (4H) ONE; 2,4,5 TRIMETHYLPYRANO[2,3,4 IJ]ISOQUINOLIN 8 (4H) ONE BENZYL ETHER BUTYL ETHER METHYL ETHER; 2,5 DIMETHYLPYRANO[2,3,4 IJ]ISOQUINOLIN 8 YLTRIFLUOROMETHANESULFONATE; 2,5 DIMETHYLPYRANO[2,3,4 IJ]ISOQUINOLIN 8 YLTRIFLUOROMETHANESULFONATE BENZYL ETHER BUTYL ETHER METHYL ETHER; 7 DEHYDROXYCASSIARIN A; ACETYLCASSIARIN A; ANTIMALARIAL AGENT; BENZOYLCASSIARIN A; BUTYROYLCASSIARIN A; CASSIARIN A; CASSIARIN A BENZYL ETHER; CASSIARIN A BUTYL ETHER; CASSIARIN A METHYL ETHER; NITRIC OXIDE; NITROGEN; UNCLASSIFIED DRUG; VASODILATOR AGENT;

ANIMAL TISSUE; AORTA; ARTICLE; CELL ADHESION; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; ERYTHROCYTE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; RAT; STRUCTURE ACTIVITY RELATION; VASCULAR ENDOTHELIUM; VASCULAR RING; VASODILATATION;

ANIMALS; ANTIMALARIALS; BINDING, COMPETITIVE; CELL ADHESION MOLECULES; CELL SEPARATION; ENDOTHELIAL CELLS; ENDOTHELIUM; HETEROCYCLIC COMPOUNDS, 3-RING; MALARIA, FALCIPARUM; MICROCIRCULATION; MOLECULAR STRUCTURE; NITRIC OXIDE; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; VASODILATION;

FABACEAE; PLASMODIUM FALCIPARUM; RATTUS; SENNA SIAMEA;

EID: 72149117971     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.013     Document Type: Article

References (32)

1. Wiesner J., Ortmann R., Jomaa H., and Schlitzer M. Angew. Chem., Int. Ed. 42 (2003) 5274
2. Greenwood B., and Mutabingwa T. Nature 415 (2002) 670
3. Wyler D.J. Clin. Infect. Dis. 16 (1993) 449
4. Taylor W.R.J., and White N.J. Drug Safety 27 (2004) 25
5. Gelb M.H., and Hol W.G.J. Science 297 (2002) 343
6. Talisuna A.O., Bloland P., and D'Alessandro U. Clin. Microbiol. Rev. 17 (2004) 235
7. Gelb M.H. Curr. Opin. Chem. Biol. 11 (2007) 440
8. Delhaes L., Benoit-Vical F., Camus D., Capron M., and Meunier B. Drugs 6 (2003) 674
9. Muhammad I., and Samoylenko V. Expert Opin. Drug. Discov. 2 (2007) 1065
10. Dunbar D.C., Li X.-C., and Muhammad I. Biomater. Aquat. Terr. Org. (2006) 207
11. Ghigo D., Todde R., Ginsburg H., Costamagna C., Gautret P., Bussolino F., Ulliers D., Giribaldi G., Deharo E., Gabrielli G., Pescarmona G., and Bosia A. J. Exp. Med. 182 (1995) 677
12. Sobolewski P., Gramaglia I., Frangos J., Intaglietta M., and van der Heyde H.C. Trends Parasitol. 21 (2005) 415
13. Yeo T.W., Lampah D.A., Gitawati R., Tjitra E., Kenangalem E., McNeil Y.R., Darcy C.J., Granger D.L., Weinberg J.B., Lopansri B.K., Price R.N., Duffull S.B., Celermajer D.S., and Anstey N.M. J. Exp. Med. 204 (2007) 2693
14. Serirom S., Raharjo W.H., Chotivanich K., Loareesuwan S., Kubes P., and Ho M. Am. J. Pathol. 162 (2003) 1651
15. Weinberg J.B., Lopansri B.K., Mwaikambo E., and Granger D.L. Curr. Opin. Infect. Dis. 21 (2008) 468
16. Yeo T.W., Lampah D.A., Gitawati R., Tjitra E., Kenangalem E., McNeil Y.R., Darcy C.J., Granger D.L., Weinberg J.B., Lopansri B.K., Price R.N., Duffull S.B., Celermajer D.S., and Anstey N.M. J. Infect. Dis. 198 (2008) 602
17. Morita H., Oshimi S., Hirasawa Y., Koyama K., Honda T., Ekasari W., Indrayanto G., and Zaini N.C. Org. Lett. 9 (2007) 3691
18. Oshimi S., Tomizawa Y., Hirasawa Y., Honda T., Widyawaruyanti A., Rudyanto M., Ekasari W., Indrayanto G., Zaini N.C., and Morita H. Bioorg. Med. Chem. Lett. 18 (2008) 3761
19. Rudyanto M., Tomizawa Y., Morita H., and Honda T. Org. Lett. 10 (2008) 1921
20. Oshimi, S.; Deguchi, J.; Hirasawa, Y.; Ekasari, W.; Wahyuni, T. S.; Zaini, N. C.; Shirota, O.; Morita, H. J. Nat. Prod. 2009, 72, 1899-1901.
21. Mbatchi S.F., Mbatchi B., Banzouzi J.T., Bansimba T., Nsonde Ntandou G.F., Ouamba J.M., Berry A., and Benoit-Vical F. J. Ethnopharmacol. 104 (2006) 168
22. Sanon S., Ollivier E., Azas N., Mahiou V., Gasquet M., Ouattara C.T., Nebie I., Traore A.S., Esposito F., Balansard G., Timon-David P., and Fumoux F. J. Ethnopharmacol. 86 (2003) 143
23. Ekasari W., Widyawaruyanti A., Zaini N.C., Syafruddin D., Honda T., and Morita H. Heterocycles 78 (2009) 1831
24. Yao Y.S., and Yao Z.J. J. Org. Chem. 73 (2008) 5221
25. Murti V.V.S., and Seshadri T.R. Proc. Indian Acad. Sci. Sect. A 30A (1949) 107
26. Sonogashira K., Tohda Y., and Hagihara N.A. Tetrahedron Lett. 16 (1975) 4467
27. Muller B., Kleschyov A.L., Gyorgy K., and Stoclet J.-C. Physiol. Res. 49 (2000) 19
28. Sofola O.A., Raji I., Ladipo C., and Coker H.A.B. Niger. Q. J. Hosp. Med. 18 (2008) 50
29. Wang Y.X., Poon C.I., and Pang C.C. J. Pharmacol. Exp. Ther. 267 (1993) 1091
30. Trager W., and Jensen J.B. Science 193 (1976) 673
31. Budimulja A.S., Syafruddin T.P., Wilariat P., and Marzuki S. Mol. Biochem. Parasitol. 84 (1997) 137
32. Morita H., Iizuka T., Choo C.Y., Chan K.L., Takeya K., and Kobayashi J. Bioorg. Med. Chem. Lett. 16 (2006) 4609