ethyl 7-methyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazine-3-carboxylate | 1407487-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: ethyl 7-methyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazine-3-carboxylate
• 英文别名: ethyl 7-methyl-1,1-dioxo-4H-1λ6,2,4-benzothiadiazine-3-carboxylate
• CAS: 1407487-06-2
• 化学式: C₁₁H₁₂N₂O₄S
• 分子量: 268.293
• InChiKey: NLHPHPSPNRJFTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 7-methyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazine-3-carboxylate 、 6-溴-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-胺 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到N-(6-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-7-methyl-4H-1,2,4-benzothiadiazine-3-carboxamide 1,1-dioxide
  参考文献：
  名称：

  Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells

  摘要：

  N-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides were prepared and evaluated on rat uterus, rat aortic rings and rat pancreatic beta-cells. Pharmacological studies conducted on rat uterus indicated that several of these original hybrid compounds displayed a strong myorelaxant activity. The most active compounds hold a bromine atom at the 6-position of the dihydrobenzopyran ring. Moreover, the compounds failed to display a marked inhibitory effect on insulin secretion and vascular myogenic activity. These features suggest that the 6-bromo compounds could be relatively selective towards the uterine smooth muscle. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.011
• 作为产物：
  描述：

  N-(p-toluenyl)-N'-(chlorosulfonyl)-urea 在 aluminum (III) chloride 、 硫酸 、 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 ethyl 7-methyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazine-3-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells

  摘要：

  N-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides were prepared and evaluated on rat uterus, rat aortic rings and rat pancreatic beta-cells. Pharmacological studies conducted on rat uterus indicated that several of these original hybrid compounds displayed a strong myorelaxant activity. The most active compounds hold a bromine atom at the 6-position of the dihydrobenzopyran ring. Moreover, the compounds failed to display a marked inhibitory effect on insulin secretion and vascular myogenic activity. These features suggest that the 6-bromo compounds could be relatively selective towards the uterine smooth muscle. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.011

文献信息

• Synthesis and pharmacological activity of N-(2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides on rat uterus, rat aorta and rat pancreatic β-cells
  作者：Smail Khelili、Nadjib Kihal、Mohamed Yekhlef、Pascal de Tullio、Philippe Lebrun、Bernard Pirotte

  DOI：10.1016/j.ejmech.2012.05.011

  日期：2012.8

  N-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamides 1,1-dioxides were prepared and evaluated on rat uterus, rat aortic rings and rat pancreatic beta-cells. Pharmacological studies conducted on rat uterus indicated that several of these original hybrid compounds displayed a strong myorelaxant activity. The most active compounds hold a bromine atom at the 6-position of the dihydrobenzopyran ring. Moreover, the compounds failed to display a marked inhibitory effect on insulin secretion and vascular myogenic activity. These features suggest that the 6-bromo compounds could be relatively selective towards the uterine smooth muscle. (C) 2012 Elsevier Masson SAS. All rights reserved.