New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA
AbstractThere 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
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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.
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(3):4307-4318.Chicago/Turabian Style
Li, Bi; Yan, Wenqiang; Zhang, Chenze; Zhang, Yuzhong; Liang, Miao; Chu, Fuhao; Gong, Yan; Xu, Bing; Wang, Penglong; Lei, Haimin. 2015. "New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA." Molecules 20, no. 3: 4307-4318.