cyclopropylbis(3-methyl-2-thienyl)methanol | 148319-26-0

• 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: cyclopropylbis(3-methyl-2-thienyl)methanol
• 英文别名: Cyclopropylbis(3-methylthiophen-2-yl)methanol；cyclopropyl-bis(3-methylthiophen-2-yl)methanol
• CAS: 148319-26-0
• 化学式: C₁₄H₁₆OS₂
• 分子量: 264.412
• InChiKey: VPXBMDQRZUEWOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  cyclopropylbis(3-methyl-2-thienyl)methanol 在 sodium hydroxide 、 氢溴酸 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 溶剂黄146 、 丙酮 为溶剂， 反应 49.5h， 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：

  双(3-甲基-2-噻吩基)甲醇 在 manganese(IV) oxide 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 cyclopropylbis(3-methyl-2-thienyl)methanol
  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

• N-(butenyl substituted) azaheterocyclic carboxylic acids
  申请人：Novo Nordisk A/S.

  公开号：US05010090A1

  公开（公告）日：1991-04-23

  1-Aminobut-3-en derivatives having optionally substituted furanyl, thienyl, pyridyl and/or pyrrolyl in the 4-position and 3-carboxypiperidin-1-yl, 3-carboxytetrahydropyrid-1-yl or 3 carboxymethylpyrrolidin-1-yl in the 1-position potentiate GABA-ergic neurotransmission.

  在1-位置具有3-羧基哌啶-1-基，3-羧基四氢吡啶-1-基或3-羧甲基吡咯烷-1-基，并在4-位置上选择性地取代呋喃基，噻吩基，吡啶基和/或吡咯基的1-氨基丁-3-烯衍生物，能够增强GABA能神经递质的传递。
• J. Med. Chem. 1993, 36, 1716-1725
  作者：

  DOI：——

  日期：——