2-(3-pyridyl)-1,2-isothiazolidine-1,1-dioxide | 158089-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 2-(3-pyridyl)-1,2-isothiazolidine-1,1-dioxide
• 英文别名: 2-(Pyridin-3-yl)isothiazolidine 1,1-dioxide；2-pyridin-3-yl-1,2-thiazolidine 1,1-dioxide
• CAS: 158089-67-9
• 化学式: C₈H₁₀N₂O₂S
• 分子量: 198.246
• InChiKey: BTISFQUSQDHPRX-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±34.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-pyridyl)-1,2-isothiazolidine-1,1-dioxide 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.0h， 生成 2,6-ditert-butyl-4-[(E)-(1,1-dioxo-2-pyridin-3-yl-1,2-thiazolidin-5-ylidene)methyl]phenol
  参考文献：
  名称：

  Novel Antiarthritic Agents with 1,2-Isothiazolidine-1,1-dioxide (γ-Sultam) Skeleton: Cytokine Suppressive Dual Inhibitors of Cyclooxygenase-2 and 5-Lipoxygenase

  摘要：

  Various 1,2-isotkiazolidine-1,1-dioxide (gamma-sultam) derivatives containing an antioxidant moiety, 2i6-di-tert-butylphenol substituent, were prepared. Some compounds, which have a lower alkyl group at the 2-position of the gamma-sultam skeleton, showed potent inhibitory effects on both cyclooxygenase (COX)-2 and 5-lipoxygenase (5-LO), as well as production of interleukin (IL)-1 in in vitro assays. They also proved to be effective in several animal arthritic models without any ulcerogenic activities. Among these compounds, (E)-(5)-(3,5-di-tert-butyl-4-hydroxybenzyliclene)-2-ethyl-1,2-isothiazolidine-1, (S-2474) was selected as an antiarthritic drug candidate and is now under clinical trials. The structure-activity relationships (SAR) examined and some pharmacological evaluations are described.

  DOI：

  10.1021/jm9906015
• 作为产物：
  描述：

  3-溴吡啶 、 异噻唑烷 1,1-二氧化物 在 copper(l) iodide 、 potassium carbonate 、 1,3-二(2-吡啶基)-1,3-丙二酮 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以70%的产率得到2-(3-pyridyl)-1,2-isothiazolidine-1,1-dioxide
  参考文献：
  名称：

  Cross coupling of 3-bromopyridine and sulfonamides (R1NHSO2R2·R1=H, Me, alkyl; R2=alkyl and aryl) catalyzed by CuI/1,3-di(pyridin-2-yl)propane-1,3-dione

  摘要：

  N-(3-Pyridinyl)-substituted secondary and tertiary sulfonamides have been synthesized in good to excellent yields by the reaction of 3-bromopyridine with primary and secondary alkyl and aryl sulfonamides (MeSO2NH2, MeSO2NHMe, TolSO(2)NH(2), TolSO(2)NHMe, 1,3-propanesultam, and 1,4-butanesultam), catalyzed by CuI (20 mol %) and 1,3-di(pyridin-2-yl)propane-1,3-dione (20 mol %) with K2CO3 (200 mol %) in DMF (0.17 M for ArBr) at 110-120 degrees C over 36-40 h. 2-Bromopyridine, 4-bromopyridine, and a wide variety of substituted phenyl bromides can also be successfully coupled with sulfonamides under these reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.037