6-{[4,4-bis(3-methylthien-2-yl)but-3-enyl]methylamino}cyclohex-1-enecarboxylic acid ethyl ester | 1426151-43-0

• 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-methylthien-2-yl)but-3-enyl]methylamino}cyclohex-1-enecarboxylic acid ethyl ester
• 英文别名: Ethyl 6-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexene-1-carboxylate；ethyl 6-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexene-1-carboxylate
• CAS: 1426151-43-0
• 化学式: C₂₄H₃₁NO₂S₂
• 分子量: 429.648
• InChiKey: RDKZBEMIAUGUBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-{[4,4-bis(3-methylthien-2-yl)but-3-enyl]methylamino}cyclohex-1-enecarboxylic acid ethyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以33%的产率得到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
• 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 作用下， 以 二氯甲烷 为溶剂， 生成 6-{[4,4-bis(3-methylthien-2-yl)but-3-enyl]methylamino}cyclohex-1-enecarboxylic acid ethyl ester
  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