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 1 H-NMR, 13 C-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.

Comparative analysis of the main active components and hypoglycemic effects after the compatibility of Scutellariae Radix and Coptidis Rhizoma

“…Previous studies have confirmed that the main acid‐base compositions of Huang‐Lian‐Jie‐Du‐Tang were baicalin and berberine, which were the major components from SR and CR, respectively. Besides, the baicalin‐berberine complex was obtained by crystallization . Recently, “multiple components against multiple targets” is continually proposed as the therapeutic principle of herb pair, and it has been experimentally verified by several cases .…”

Facile Synthesis and Anticancer Activity Study of Novel Series of Substituted and Fused Coumarin Derivatives

“…1). Furthermore, cinnamoyl-5-hydroxycoumarin derivative 12 was obtained through fusion of equivalent amounts of cinnamoyl chloride 11 [24] and compound 1. 5-Hydroxycoumarin derivative 1 upon heating under reflux with one equivalent of 3-(4-chlorophenyl)-1H-1,2,4-triazol-5-amine 9 [23] in dimethyl sulfoxide yielded the novel (1H-1,2,4-triazol-5-ylamino)coumarin derivative 10.…”

Progress in the synthesis of δ-sultones

“…A broad variety of enolate-type nucleophilic addition reactions to access differently ring-sized sultones have been reported in the past [ 12 , 13 , 88 – 95 ], either via cyclization/addition of sulfonate-based carbanions to an adjacent electrophilic position (e.g., an ester or an aldehyde) or by adding enolates to activated electrophilic sulfuric acid species. In 1972 already, Timoney et al carried out the base-mediated cyclization of mesylates 68 to access the bicyclic δ-sultones 69 , albeit in low yield [ 88 ].…”

“…Over the decades, these compounds have received considerable attention (for some earlier general reviews, please see [ 2 – 6 ]). The interest in these heterocycles is either due to their biological properties themselves (please refer to [ 7 – 13 ] for some selected case studies of sultones in medicinal chemistry) or because of their versatility as intermediates for further transformations, such as, e.g., sulfoalkylations or desulfurizations, to mention a few examples only (which is very nicely discussed in a recent review by Mondal [ 6 ]). Like lactones, these sulfur analogues can be classified according to their ring size as β-, γ-, δ-, or ε-sultones.…”