3-acetylthio-4-aminocarbonylpiperidine-1-carboxylic acid methyl ester | 654666-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-acetylthio-4-aminocarbonylpiperidine-1-carboxylic acid methyl ester
• 英文别名: methyl 3-acetylsulfanyl-4-carbamoylpiperidine-1-carboxylate
• CAS: 654666-63-4
• 化学式: C₁₀H₁₆N₂O₄S
• 分子量: 260.314
• InChiKey: AWOACSUAUZLHGH-UHFFFAOYSA-N

物化性质

• 沸点：
  462.0±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  89.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-acetylthio-4-aminocarbonylpiperidine-1-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 methyl 4-carbamoyl-3-sulfanylpiperidine-1-carboxylate
  参考文献：
  名称：

  Aza-THIP and related analogues of THIP as GABA C antagonists

  摘要：

  The potency of a series of eight compounds structurally related with 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol (THIP), a potent GABA(A) partial agonist exhibiting GABA(C) rho(1) antagonist effect (K-i = 25 muM), was determined electrophysiologically using homomeric human GABA(C) rho(1) receptors expressed in Xenopus oocytes. Protolytic properties (pK(a) values for the acidic bioisosteric groups) and the presence of steric bulk in the molecules appear to be structural parameters of importance for blockade of the GABA(C) rho(1) receptor. Within this series of moderately potent GABA(C) antagonists, only 4,5,6,7-tetrahydropyrazolo[5,4-c]pyridin-3-ol (Aza-THIP) does not interact delectably with GABA(A) receptors, and Aza-THIP has the potential of being a useful tool for molecular and behavioural pharmacological studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.016
• 作为产物：
  描述：

  4-吡啶甲酰胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 122.5h， 生成 3-acetylthio-4-aminocarbonylpiperidine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Aza-THIP and related analogues of THIP as GABA C antagonists

  摘要：

  The potency of a series of eight compounds structurally related with 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol (THIP), a potent GABA(A) partial agonist exhibiting GABA(C) rho(1) antagonist effect (K-i = 25 muM), was determined electrophysiologically using homomeric human GABA(C) rho(1) receptors expressed in Xenopus oocytes. Protolytic properties (pK(a) values for the acidic bioisosteric groups) and the presence of steric bulk in the molecules appear to be structural parameters of importance for blockade of the GABA(C) rho(1) receptor. Within this series of moderately potent GABA(C) antagonists, only 4,5,6,7-tetrahydropyrazolo[5,4-c]pyridin-3-ol (Aza-THIP) does not interact delectably with GABA(A) receptors, and Aza-THIP has the potential of being a useful tool for molecular and behavioural pharmacological studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.016