Publication: Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters
Issued Date
2004-08-26
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ISSN
00222623
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2-s2.0-4143061295
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Medicinal Chemistry. Vol.47, No.18 (2004), 4427-4438
Suggested Citation
Ngampong Kongkathip, Suwaporn Luangkamin, Boonsong Kongkathip, Chak Sangma, Ronald Grigg, Palangpon Kongsaeree, Samran Prabpai, Narathip Pradidphol, Suratsawadee Piyaviriyagul, Pongpun Siripong Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters. Journal of Medicinal Chemistry. Vol.47, No.18 (2004), 4427-4438. doi:10.1021/jm030323g Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/21165
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Title
Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters
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Abstract
Rhinacanthin-M, -N and -Q, natural products isolated from the medicinal plant Rhinacanthus nasutus, and 39 novel naphthoquinone esters have been synthesized in excellent yield by esterification of naphthoquinone-3-(propan- 3′-ols) with benzoic or naphthoic acids. Almost all the naphthoquinone esters that contain a C-3 hydroxy group showed significant cytotoxicities against KB, HeLa, and HepG2 cell lines. In contrast, ester derivatives lacking the C-3 hydroxy group were inactive to the cancer cell lines. Two methyl substituents on the C-2′ of propyl chain conferred more potent cytotoxicity than when there is only one or no methyl group. Naphthoate esters exhibited greater cytotoxicity than benzoate esters. Computer modeling has been done to obtain a first look at the mode of action in connection with these observations.