title: New synthesis method for sultone derivatives: synthesis, crystal structure and biological evaluation of S-CA.
abstract: 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.
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. libimegan@163.com.
authors: Bi
authors: B
authors: Li
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. ywq3226925@163.com.
authors: Wenqiang
authors: W
authors: Yan
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. zcz920418@163.com.
authors: Chenze
authors: C
authors: Zhang
authors: School of Basic Medicine, Beijing University of Chinese Medicine, Beijing 100029, China. zyz100102@126.com.
authors: Yuzhong
authors: Y
authors: Zhang
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. mimi1111202@sina.com.
authors: Miao
authors: M
authors: Liang
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. chufhao@163.com.
authors: Fuhao
authors: F
authors: Chu
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. gongyan90@163.com.
authors: Yan
authors: Y
authors: Gong
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. weichenxubing@126.com.
authors: Bing
authors: B
authors: Xu
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. wpl581@126.com.
authors: Penglong
authors: P
authors: Wang
authors: School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China. hm_lei@126.com.
authors: Haimin
authors: H
authors: Lei
mesh_terms: D020533:Angiogenesis Inhibitors / Q000008:administration & dosage* / Q000009:adverse effects / Q000138:chemical synthesis*; D000818:Animals; D000970:Antineoplastic Agents / Q000008:administration & dosage* / Q000009:adverse effects / Q000138:chemical synthesis*; D001859:Bone Neoplasms / Q000188:drug therapy; D045744:Cell Line, Tumor; D002642:Chick Embryo; D049033:Chorioallantoic Membrane / Q000098:blood supply; D004305:Dose-Response Relationship, Drug; D007274:Injections, Intraperitoneal; D051379:Mice; D015394:Molecular Structure; D009368:Neoplasm Transplantation; D010075:Oxathiins / Q000008:administration & dosage* / Q000009:adverse effects / Q000138:chemical synthesis*; D012509:Sarcoma / Q000188:drug therapy
chemical_list: D020533:Angiogenesis Inhibitors; D000970:Antineoplastic Agents; D010075:Oxathiins