(E)-4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenol

• 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: (E)-4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenol
• 英文别名: (E)-4-(3-methylthiophen-2-yl)-4-thiophen-2-ylbut-3-en-1-ol
• 化学式: C₁₃H₁₄OS₂
• 分子量: 250.386
• InChiKey: BIAPFTONEAEEHW-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-1-(2-噻吩基)丁酮 在 盐酸 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.25h， 生成 (E)-4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenol
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (Tiagabine) as an anticonvulsant drug candidate

  摘要：

  A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [H-3]-GABA uptake in rat synaptosomes was determined for each compound. It was found that the most potent examples are those having a substituent in an ''ortho'' position in one or both aromatic/heteroaromatic groups. The majority of the compounds described are structurally related to tiagabine, (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride (NNC 05-0328) and some of the reasoning behind the selection of this compound as a drug candidate is summarized.

  DOI：

  10.1021/jm00064a005

文献信息

• US5010090A
  申请人：——

  公开号：US5010090A

  公开（公告）日：1991-04-23