ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate | 148319-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate
• 英文别名: ethyl (S)-1-[4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl]-3-piperidinecarboxylate；ethyl (3S)-1-[4-(3-methylthiophen-2-yl)-4-thiophen-2-ylbut-3-enyl]piperidine-3-carboxylate
• CAS: 148319-28-2
• 化学式: C₂₁H₂₇NO₂S₂
• 分子量: 389.583
• InChiKey: MQGKWUAHOVWZBB-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylic acid
  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：

  4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenol 在 吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 212.0h， 生成 ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate
  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

• 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
  作者：Knud Erik Andersen、Claus Braestrup、Frederik C. Groenwald、Anker S. Joergensen、Erik B. Nielsen、Ursula Sonnewald、Per O. Soerensen、Peter D. Suzdak、Lars J. S. Knutsen

  DOI：10.1021/jm00064a005

  日期：1993.6

  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.