3-Butyl-5,5-dimethyl-2,2-dioxooxathiazolidin-4-one | 1422432-19-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 3-Butyl-5,5-dimethyl-2,2-dioxooxathiazolidin-4-one
• CAS: 1422432-19-6
• 化学式: C₈H₁₅NO₄S
• 分子量: 221.277
• InChiKey: YVFYYAQSLHBKKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3-Butyl-5,5-dimethyl-2,2-dioxooxathiazolidin-4-one
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of bioisosteres of trimethadione, N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides from α-hydroxyamides

  摘要：

  The synthesis and anticonvulsant activity of novel heterocycles N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides, bioisosteres of trimethadione (TMD, oxazolidine-2,4-dione) and phenytoin (PHE), are described. TMD is an anticonvulsant drug widely used against absences seizures in the early 80's and PHE is an antiepileptic drug with a wide spectrum activity. The intermediates of synthesis of N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides, alpha-hydroxyamides, were obtained using microwave assisted synthesis. Anticonvulsant screening was performed in mice after intraperitoneal administration in the maximal electroshock seizure test (MES) and subcutaneous pentylenetetrazole seizures test (scPTZ). These new compounds showed a wide spectrum activity and were no neurotoxic in the RotoRod test. alpha-Hydroxyamides and N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides were 3-4700 times more potent than valproic acid in the MES test. Quantification of anticonvulsant protection was calculated (ED50) for the most active candidates; alpha-hydroxyamides 3a-c and 3e, and N-derivative-oxathiazolidine-4-one-2,2-dioxides 5a-c with ED50 values of 9.1, 53.9, 44.6, 25.2, 15.1, 91.1 and 0.06 mg/kg, respectively, in the MES test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.033