2-hexyl-3-methyl-1,1-dioxo-1,2-dihydro-1^λ6-1,2,6-thiadiazine-5-carboxylic acid ethyl ester | 936756-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-hexyl-3-methyl-1,1-dioxo-1,2-dihydro-1^λ6-1,2,6-thiadiazine-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 6-hexyl-5-methyl-1,1-dioxo-1,2,6-thiadiazine-3-carboxylate
• CAS: 936756-44-4
• 化学式: C₁₃H₂₂N₂O₄S
• 分子量: 302.395
• InChiKey: YCADXTVXSULEAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hexyl-3-methyl-1,1-dioxo-1,2-dihydro-1^λ6-1,2,6-thiadiazine-5-carboxylic acid ethyl ester 、 1-氨基哌啶 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以22%的产率得到6-hexyl-5-methyl-1,1-dioxo-N-piperidin-1-yl-1,2,6-thiadiazine-3-carboxamide
  参考文献：
  名称：

  Discovery of 1,1-dioxo-1,2,6-thiadiazine-5-carboxamide derivatives as cannabinoid-like molecules with agonist and antagonist activity

  摘要：

  A series of new 2-substituted 1,1-dioxo-1,2,6-thiadiazine-5-carboxylate derivatives have been prepared from monosubstituted sulfamides in order to obtain N-substituted1,1-dioxo-1,2,6-thiadiazine-5-carboxamides as novel cannabinoid derivatives, analogues of Rimonabant (SR141716A). Their potential functional activity on cannabinoid receptors has been evaluated in vitro and in vivo in mice, showing that two compounds (37 and 39) behave as cannabinoid agonists in vitro. Their potency is lower than that of the reference compound, WIN 55,212-2, but their efficacy is similar to that of this cannabinoid agonist, although no in vivo activity is observed. Another derivative (38) behaves as a cannabinoid antagonist both in vitro and in vivo, being its efficacy and potency similar to that of the well-known antagonist SR141716A. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.056
• 作为产物：
  描述：

  N-(hexyl)sulfamide 、 乙酰丙酮酸乙酯 在 盐酸 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 24.0h， 以50%的产率得到2-hexyl-3-methyl-1,1-dioxo-1,2-dihydro-1^λ6-1,2,6-thiadiazine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of 1,1-dioxo-1,2,6-thiadiazine-5-carboxamide derivatives as cannabinoid-like molecules with agonist and antagonist activity

  摘要：

  A series of new 2-substituted 1,1-dioxo-1,2,6-thiadiazine-5-carboxylate derivatives have been prepared from monosubstituted sulfamides in order to obtain N-substituted1,1-dioxo-1,2,6-thiadiazine-5-carboxamides as novel cannabinoid derivatives, analogues of Rimonabant (SR141716A). Their potential functional activity on cannabinoid receptors has been evaluated in vitro and in vivo in mice, showing that two compounds (37 and 39) behave as cannabinoid agonists in vitro. Their potency is lower than that of the reference compound, WIN 55,212-2, but their efficacy is similar to that of this cannabinoid agonist, although no in vivo activity is observed. Another derivative (38) behaves as a cannabinoid antagonist both in vitro and in vivo, being its efficacy and potency similar to that of the well-known antagonist SR141716A. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.056