6-[4,4-Bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexene-1-carboxylic acid;hydrochloride | 1426151-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 6-[4,4-Bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexene-1-carboxylic acid;hydrochloride
• 英文别名: 6-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexene-1-carboxylic acid;hydrochloride
• CAS: 1426151-33-8
• 化学式: C₂₂H₂₇NO₂S₂*ClH
• 分子量: 438.055
• InChiKey: GRTCDSJGJOWCRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester 在 吡啶 、 双(乙腈)氯化钯(II) 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 6-[4,4-Bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexene-1-carboxylic acid;hydrochloride
  参考文献：
  名称：

  Selective mGAT2 (BGT-1) GABA Uptake Inhibitors: Design, Synthesis, and Pharmacological Characterization

  摘要：

  beta-Amino acids sharing a lipophilic diaromatic side chain were synthesized and characterized pharmacologically on mouse GABA transporter subtypes mGAT1-4. The parent amino acids were also characterized. Compounds 13a, 13b, and 17b displayed more than 6-fold selectivity for mGAT2 over mGAT1. Compound 17b displayed anticonvulsive properties inferring a role of mGAT2 in epileptic disorders. These results provide new neuropharmacological tools and a strategy for designing subtype selective GABA transport inhibitors.

  DOI：

  10.1021/jm301872x

文献信息

• Selective mGAT2 (BGT-1) GABA Uptake Inhibitors: Design, Synthesis, and Pharmacological Characterization
  作者：Stine B. Vogensen、Lars Jørgensen、Karsten K. Madsen、Nrupa Borkar、Petrine Wellendorph、Jonas Skovgaard-Petersen、Arne Schousboe、H. Steve White、Povl Krogsgaard-Larsen、Rasmus P. Clausen

  DOI：10.1021/jm301872x

  日期：2013.3.14

  beta-Amino acids sharing a lipophilic diaromatic side chain were synthesized and characterized pharmacologically on mouse GABA transporter subtypes mGAT1-4. The parent amino acids were also characterized. Compounds 13a, 13b, and 17b displayed more than 6-fold selectivity for mGAT2 over mGAT1. Compound 17b displayed anticonvulsive properties inferring a role of mGAT2 in epileptic disorders. These results provide new neuropharmacological tools and a strategy for designing subtype selective GABA transport inhibitors.