623588-79-4Relevant articles and documents
Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents
Kongkathip, Ngampong,Pradidphol, Narathip,Hasitapan, Komkrit,Grigg, Ronald,Kao, Wei-Chun,Hunte, Carola,Fisher, Nicholas,Warman, Ashley J.,Biagini, Giancarlo A.,Kongsaeree, Palangpon,Chuawong, Pitak,Kongkathip, Boonsong
scheme or table, p. 1211 - 1221 (2010/08/07)
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.
TYPE 1, 4-NAPHTOQUINONE COMPOUNDS, COMPOSITIONS COMPRISING THEM AND USE OF THESE COMPOUNDS AS ANTI-CANCER AGENTS
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Page/Page column 25, (2009/10/06)
This invention relates to compounds with the formula (I) given below or one of their pharmaceutically acceptable salts, as a medicine; Formula (I) of pharmaceutical compositions comprising one or more compounds with Formula (I) as active constituent, use
Microwave-assisted solid-phase D?tz benzannulation reaction: A facile synthesis of 2,3-disubstituted-1,4-naphthoquinones
Shanmugasundaram, Muthian,Garcia-Martinez, Israel,Li, Qingyi,Estrada, Abril,Martinez, Nancy E.,Martinez, Luis E.
, p. 7545 - 7548 (2007/10/03)
A microwave-assisted solid-supported D?tz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1, 4-naphthoquinone derivatives in good to moderate yields with high purities.
Synthesis of novel rhinacanthins and related anticancer naphthoquinone esters
Kongkathip, Ngampong,Luangkamin, Suwaporn,Kongkathip, Boonsong,Sangma, Chak,Grigg, Ronald,Kongsaeree, Palangpon,Prabpai, Samran,Pradidphol, Narathip,Piyaviriyagul, Suratsawadee,Siripong, Pongpun
, p. 4427 - 4438 (2007/10/03)
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 naphthoi
Potent antitumor activity of synthetic 1,2-naphthoquinones and 1,4-naphthoquinones
Kongkathip, Ngampong,Kongkathip, Boonsong,Siripong, Pongpun,Sangma, Chak,Luangkamin, Suwaporn,Niyomdecha, Momad,Pattanapa, Suppachai,Piyaviriyagul, Suratsawadee,Kongsaeree, Palangpon
, p. 3179 - 3191 (2007/10/03)
Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG2) with IC50 values of 0.92-9.63 μM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC50 values of 7.61-24.13 μM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with similar cytotoxicity as 1,2-pyranonaphthoquinones. In comparison to 1,2-naphthoquinones, six 1,4-naphthoquinones derivatives fused with pyran ring (8-10) and furan ring (11-13) were synthesized and they showed less cytotoxicity or inactive to the cancer cell lines. Moreover, compound 13 had significant cytotoxicity against HeLa cell line (IC50 value of 9.25 μM) while it showed no toxic to vero cell.
