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Kongkathip, Ngampong, Pradidphol, Narathip, Hasitapan, Komkrit, Grigg, Ronald, Kao, Wei-Chun, Hunte, Carola, Fisher, Nicholas, Warman, Ashley, Biagini, Giancarlo 
ORCID: https://orcid.org/0000-0001-6356-6595, Kongsaeree, Palangpon, Chuawong, Pitak and Kongkathip, Boonsong
(2010)
'Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents.'. Journal of medicinal chemistry, Vol 53, Issue 3, pp. 1211-1221.
Abstract
Twenty-six novel naphthoquinone aliphatic esters were synthesized by esterification of 1,4-naphthoquinone alcohols with various aliphatic acids. The 1,4-naphthoquinone alcohols were prepared from 1-hydroxy-2-naphthoic acid in nine steps with excellent yields. Twenty-four of the novel synthetic naphthoquinone esters showed significant antimalarial activity with IC(50) values in the range of 0.03-16.63 microM. The length of the aliphatic chain and the presence of C-2' substituents on the propyl chain affected the activity. Interestingly, compounds 31 and 37 showed very good antimalarial activity and were not toxic to normal Vero cells, and the PTI values of 31 (>1990.38) and 37 (1825.94) are excellent. Both 31 and 37 showed potent inhibition against P. falciparum 3D7 cyt bc(1) and no inhibition on rat cyt bc(1). They showed IC(50) values in the nanomolar range, providing full inhibition of cyt bc(1) with one molecule inhibitor bound per cyt bc(1) monomer at the Q(o) site.
| Item Type: | Article |
|---|---|
| Subjects: | QV Pharmacology > Anti-Inflammatory Agents. Anti-Infective Agents. Antineoplastic Agents > QV 256 Antimalarials QV Pharmacology > QV 34 Experimental pharmacology (General) |
| Faculty: Department: | Groups (2002 - 2012) > Molecular & Biochemical Parasitology Group |
| Digital Object Identifer (DOI): | https://doi.org/10.1021/jm901545z |
| Depositing User: | Mary Creegan |
| Date Deposited: | 05 Jul 2010 10:34 |
| Last Modified: | 06 Feb 2018 13:00 |
| URI: | https://archive.lstmed.ac.uk/id/eprint/1032 |
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