Abstract
An improved method for the synthesis of (6′R)-6′-C-methylneplanocin A (RMNPA, 2), a potent S-adenosyl-L-homocysteine (AdoHcy) hydrolase inhibitor, was developed via a chelation-controlled stereoselective addition of MeTiCl3 to the neplanocin A 6′-aldehyde derivative 6. Compound 2 effectively inhibited the growth of malaria parasites both in vitro and in vivo. The antimalarial EC50 value of 2 against Plasmodium berghei in mice was 1.0 mg/kg/day, which was superior to that of chloroquine (EC50 = 1.8 mg/kg/day).
| Original language | English |
|---|---|
| Pages (from-to) | 748-751 |
| Number of pages | 4 |
| Journal | Journal of medicinal chemistry |
| Volume | 45 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - Jan 31 2002 |
ASJC Scopus subject areas
- Molecular Medicine
- Drug Discovery
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Shuto, S., Minakawa, N., Niizuma, S., Kim, H. S., Wataya, Y., & Matsuda, A. (2002). New neplanocin analogues. 12. Alternative synthesis and antimalarial effect of (6′R)-6′-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor. Journal of medicinal chemistry, 45(3), 748-751. https://doi.org/10.1021/jm010374i