New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA
Open Access
- 6 March 2015
- Vol. 20 (3) , 4307-4318
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.Keywords
This publication has 21 references indexed in Scilit:
- Recent Developments in the Synthesis and Application of SultonesChemical Reviews, 2012
- Synthesis and Biological Evaluation of New Ligustrazine Derivatives as Anti-Tumor AgentsMolecules, 2012
- Extracts of Lycoris aurea Induce Apoptosis in Murine Sarcoma S180 CellsMolecules, 2012
- From β‐Amino‐γ‐sultone to Unusual Bicyclic Pyridine and Pyrazine Heterocyclic Systems: Synthesis and Cytostatic and Antiviral ActivitiesChemMedChem, 2011
- Anti-angiogenic activity of heparin-like polysulfonated polymeric drugs in 3D human cell cultureBiomaterials, 2010
- 4-Benzyloxy-γ-Sultone Derivatives: Discovery of a Novel Family of Non-Nucleoside Inhibitors of Human Cytomegalovirus and Varicella Zoster VirusJournal of Medicinal Chemistry, 2009
- 4′′-Benzoylureido-TSAO Derivatives as Potent and Selective Non-Nucleoside HCMV Inhibitors. Structure−Activity Relationship and Mechanism of Antiviral ActionJournal of Medicinal Chemistry, 2008
- Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultoneChemical Communications, 2000
- γ-Propoxy-sulfo-lichenin, an antitumor polysaccharide derived from licheninPharmaceutica Acta Helvetiae, 1995
- Determination of reaction rate constants for alkylation of 4-(p-Nitrobenzyl) pyridine by different alkylating agentsToxicology Letters, 1980