Publication: Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents
Issued Date
2010-03-01
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ISSN
15204804
00222623
00222623
Other identifier(s)
2-s2.0-77249142352
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Medicinal Chemistry. Vol.53, No.3 (2010), 1211-1221
Suggested Citation
Ngampong Kongkathip, Narathip Pradidphol, Komkrit Hasitapan, Ronald Grigg, Wei Chun Kao, Carola Hunte, Nicholas Fisher, Ashley J. Warman, Giancarlo A. Biagini, Palangpon Kongsaeree, Pitak Chuawong, Boonsong Kongkathip Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents. Journal of Medicinal Chemistry. Vol.53, No.3 (2010), 1211-1221. doi:10.1021/jm901545z Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/28775
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Title
Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents
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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 μM. 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 bc1 and no inhibition on rat cyt bc1. They showed IC50 values in the nanomolar range, providing full inhibition of cyt bc1 with one molecule inhibitor bound per cyt bc1 monomer at the Qo site. © 2010 American Chemical Society.