3-Benzhydrylsulfanylpropan-1-ol | 908583-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Benzhydrylsulfanylpropan-1-ol
• 英文别名: 3-benzhydrylsulfanylpropan-1-ol
• CAS: 908583-32-4
• 化学式: C₁₆H₁₈OS
• 分子量: 258.384
• InChiKey: JHCXBGNMACILPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Benzhydrylsulfanylpropan-1-ol 在 咪唑 、 sodium hydroxide 、 四溴化碳 、 potassium carbonate 、 三苯基膦 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 58.0h， 生成 (R)-1-(3-(benzhydrylthio)propyl)piperidine-3-carboxylic acid hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors

  摘要：

  A series of new (R)-1-(2-diarylmethylthio/sulfinyl) ethyl-pipei-idine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1(3-diarylmethylthio) propyl-piperidine-3-carboxylic acid hydrochlorides 5'a-d were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT-1 inhibitory activities than 5a-d/5'a-d with diary]methylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3 H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.010
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 3-Benzhydrylsulfanylpropan-1-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors

  摘要：

  A series of new (R)-1-(2-diarylmethylthio/sulfinyl) ethyl-pipei-idine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1(3-diarylmethylthio) propyl-piperidine-3-carboxylic acid hydrochlorides 5'a-d were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT-1 inhibitory activities than 5a-d/5'a-d with diary]methylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3 H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.010

文献信息

• Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors
  作者：Jiange Zhang、Pei Zhang、Xianbo Liu、Kai Fang、Guoqiang Lin

  DOI：10.1016/j.bmcl.2007.04.010

  日期：2007.7

  A series of new (R)-1-(2-diarylmethylthio/sulfinyl) ethyl-pipei-idine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1(3-diarylmethylthio) propyl-piperidine-3-carboxylic acid hydrochlorides 5'a-d were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT-1 inhibitory activities than 5a-d/5'a-d with diary]methylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3 H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2007 Elsevier Ltd. All rights reserved.