1,1-二氧化物-6-氯-3-(氯甲基)-3,4-二氢-2H-1,2,4-苯并噻二嗪 | 847997-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 中文名称: 1,1-二氧化物-6-氯-3-(氯甲基)-3,4-二氢-2H-1,2,4-苯并噻二嗪
• 英文名称: 6-chloro-3-chloromethyl-3,4-dihydro-2H-1,2,4-benzothiadiazin 1,1-dioxide
• 英文别名: 6-Chloro-3-(chloromethyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；6-chloro-3-(chloromethyl)-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 847997-88-0
• 化学式: C₈H₈Cl₂N₂O₂S
• 分子量: 267.136
• InChiKey: OSYCZTIVGAQZCW-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 沸点：
  445.2±55.0 °C(Predicted)
• 密度：
  1.489±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1,1-二氧化物-6-氯-3-(氯甲基)-3,4-二氢-2H-1,2,4-苯并噻二嗪 、 邻硝基苯甲醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以37%的产率得到6-Chloro-3-chloromethyl-2-(2-nitro-benzyl)-3,4-dihydro-2H-benzo[1,2,4]thiadiazine 1,1-dioxide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors

  摘要：

  A series of 2,1,3- and 1,2,4-benzothiadiazine derivatives (BTDs) were synthesized and evaluated for their inhibitory activity versus enzymatic isoforms PDE3, PDE4 and PDE7. The compounds characterized by the 3,5-di-tert-butyl-4-hydroxybenzyl moiety at NI position of 2,1,3-benzothiadiazine core (8, 13, 18), were found active and selective at micromolar level versus PDE4 and could be studied as new leads for the treatment of asthma and COPD (Chronic Obstructive Pulmonary Disease). The antioxidant activity evaluation on the same compounds highlighted 13 as the most significative. Molecular modelling studies gave further support to biological results and suggested targeted modifications so as to improve their potency. (C)2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.055
• 作为产物：
  描述：

  氯乙醛 、 2-氨基-4-氯苯磺胺 在 氯化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95%的产率得到1,1-二氧化物-6-氯-3-(氯甲基)-3,4-二氢-2H-1,2,4-苯并噻二嗪
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors

  摘要：

  A series of 2,1,3- and 1,2,4-benzothiadiazine derivatives (BTDs) were synthesized and evaluated for their inhibitory activity versus enzymatic isoforms PDE3, PDE4 and PDE7. The compounds characterized by the 3,5-di-tert-butyl-4-hydroxybenzyl moiety at NI position of 2,1,3-benzothiadiazine core (8, 13, 18), were found active and selective at micromolar level versus PDE4 and could be studied as new leads for the treatment of asthma and COPD (Chronic Obstructive Pulmonary Disease). The antioxidant activity evaluation on the same compounds highlighted 13 as the most significative. Molecular modelling studies gave further support to biological results and suggested targeted modifications so as to improve their potency. (C)2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.055