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Open AccessCommunication
Molecules 2015, 20(3), 4307-4318; doi:10.3390/molecules20034307

New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China
School of Basic Medicine, Beijing University of Chinese Medicine, Beijing 100029, China
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 25 January 2015 / Revised: 26 February 2015 / Accepted: 27 February 2015 / Published: 6 March 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1525 KB, uploaded 13 March 2015]   |  


There has been no remarkable progress in the synthesis of sultones in recent years. To facilitate more detailed studies of this functional group, we found a new method to synthesize the sulfonic acid lactone derivatives and finish its ring-closing reaction. A new sultone derivative, (E)-ethyl 4-oxo-6-styryl-3,4-dihydro-1,2-oxathiine-5-carboxylate 2,2-dioxide (S-CA), was synthesized and structurally identified by 1H-NMR, 13C-NMR, HMQC and X-ray single crystal diffraction analysis. The new rapid synthesis extended the method of ring-closing reaction of sulfonic acid lactone derivatives. The angiogenesis activities of S-CA were evaluated by the chick chorioallantoic membrane (CAM) model. It could selectively suppress small angiogenesis in CAM, without influencing either middle and large angiogenesis. In addition, anticancer efficacy of S-CA was evaluated in vivo using a murine sarcoma S180 model. Reduction of the tumor weight and tumor HE staining regions demonstrated that S-CA (10 mg/kg, intraperitoneal injection) had potent inhibition effects and a 44.71% inhibitory rate in S180 mice. Moreover, an acute toxicity test showed that the LD50 value of S-CA via intraperitoneal injection was 25.624 mg/kg. View Full-Text
Keywords: sultone derivative; ring-closing reaction; CAM; acute toxicity; S180 sultone derivative; ring-closing reaction; CAM; acute toxicity; S180

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Li, B.; Yan, W.; Zhang, C.; Zhang, Y.; Liang, M.; Chu, F.; Gong, Y.; Xu, B.; Wang, P.; Lei, H. New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA. Molecules 2015, 20, 4307-4318.

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