Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-Adenosyl-L-homocysteine hydrolase

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 22, 2003, Pages 3963-3965

  Kitade, Yukio ^a   Kojima, Hiroharu ^a   Zulfiqur, Fazila ^a   Kim, Hye Sook ^b   Wataya, Yusuke ^b  

^a GIFU UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUOROADENINE; 2 FLUORONORARISTEROMYCIN; 4 (6 AMINO 2 FLUORO 9H PURIN 9 YL)CYCLOPENT 2 EN 1 OL; 4 ACETOXY 2 CYCLOPENTEN 1 OL; 4 METHYLMORPHOLINE N OXIDE; ADENINE DERIVATIVE; ADENOSYLHOMOCYSTEINASE INHIBITOR; ANTIPROTOZOAL AGENT; CYCLOPENTENE DERIVATIVE; MICROBIAL ENZYME; MORPHOLINE DERIVATIVE; OSMIUM TETRAOXIDE; SODIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; NONHUMAN; PLASMODIUM FALCIPARUM;

PLASMODIUM FALCIPARUM;

EID: 0242365644     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.08.074     Document Type: Article

References (19)

1. (a) Keller, B. T.; Borchardt, R. T. In Biological Methylation and Drug Design: Experimental and Clinical Roles of S-Adenosylmethionine; Borchart, R. T., Creveling, C. R., Ueland, P. M., Eds.; Humana: Clifton, NJ, 1986; p 385
2. (b) Wolfe M.S., Borchardt R.T. J. Med. Chem. 34:1991;1521
3. (c) Chiang P.K. Pharmacol. Ther. 77:1998;115, and references cited therein.
4. Wolos J.A., Frondorf K.A., Babcock G.F., Stripp S.A., Bowlin T.L. Cell. Immunol. 149:1993;402.
5. (a) Bitonti A.J., Baumann R.J., McCann P.P. Biochem. Pharmacol. 40:1990;601
6. (b) Henderson D.M., Hanson S., Allen T., Wilson K., Coulter-Karis D.E., Grrenberg M.L., Hershfield M.S., Ullman B. Mol. Biochem. Parasitol. 53:1992;169
7. (c) Wolos J.A., Frondorf K.A., Esser R.E. J. Immunol. 151:1993;526.
8. Liu S., Wolfe M.S., Borchardt R.T. Antiviral Res. 19:1992;247.
9. Creedon K.A., Rathod P.K., Wellems T.E. J. Bol. Chem. 269:1994;16364.
10. Keller B.T., Borchardt R.T. Borchardt R.T., Creveling C.R., Ueland P.M. Biological Methylation and Drug Design. 1987;385 Hummana, Clifton: NJ.
11. Nakanishi M., Iwata A., Yatome C., Kitade Y. J. Biochem. 129:2001;101.
12. Kitade Y., Kozaki A., Miwa T., Nakanishi M. Tetrahedron. 58:2002;1271.
13. (a) Montgomery J.A. Cancer Res. 42:1982;3911
14. (b) Montgomery J.A. Med. Res. Rev. 2:1982;271.
15. Trost B.M., Kou G.H., Benneche T. J. Am. Chem. Soc. 110:1988;621.
16. 5O·1/5 EtOAc: C, 51.30; H, 4.62; N, 27.70, found: C, 51.47; H, 4.77; N, 27.90 (crystallization from EtOAc).
17. 2O: C, 43.64; H, 4.64; N, 25.44. Found: C, 43.88; H, 4.50; N, 25.09 (crystallization from EtOAc).
18. The enzyme was incubated with 100 μL adenosine, 5 mM DL-homocysteine and inhibitors in 0.2 mL of 10 mM potassium phosphate, pH 7.2, buffer at 30°C for 2 min in the standard assay ststem (see ref 8). The reaction was started by the addition of 5 μL of SAH hydrolase (human: 0.43 μg, P. falciparum: 0.54 μg) and terminated by the addition of 20 μL of 0.67 N HCl. The reaction mixture was kept on ice until the HPLC analysis. The mixture was analyzed for SAH by a Shimadzu LC-10A VP HPLC system. In the synthetic reaction, one unit of SAH hydrolase was defined as the amount synthesizing 1 μmol of SAH/min at 30°C.
19. Kim H.-S., Nagai Y., Ono K., Wataya Y., Tsuchiya K., Masuyama A., Nojima M., Mccullough K.J. J. Med. Chem. 44:2001;2357.