4-溴-1,1-双(3-甲基噻吩-2-基)-1-丁醇 | 922184-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 4-溴-1,1-双(3-甲基噻吩-2-基)-1-丁醇
• 英文名称: 4-Bromo-1,1-bis-(3-methyl-thiophen-2-yl)-butan-1-ol
• 英文别名: 4-Bromo-1,1-bis(3-methylthiophen-2-yl)butan-1-ol
• CAS: 922184-80-3
• 化学式: C₁₄H₁₇BrOS₂
• 分子量: 345.324
• InChiKey: YBOQEMFWUYGARI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴-1,1-双(3-甲基噻吩-2-基)-1-丁醇 在 sodium hydroxide 、 硫酸 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 异丙醇 、 丙酮 为溶剂， 反应 51.0h， 生成 噻加宾
  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
• 作为产物：
  描述：

  2-溴-3-甲基噻吩 、 4-溴丁酸乙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以60%的产率得到4-溴-1,1-双(3-甲基噻吩-2-基)-1-丁醇
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of the N-diarylalkenyl-piperidinecarboxylic acid derivatives as GABA uptake inhibitors (I)

  摘要：

  Twenty novel N-diarylalkenyl-piperidinecarboxylic acid derivatives were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors. The biological assay showed that (R)-1-[4,4-bis(3-phenoxymethyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic hydrochloride (4e) possessed almost as strong GAT1 inhibitory activity as tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.004