4,4-di(thien-2-yl)but-3-enyl bromide | 109857-80-9

• 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: 4,4-di(thien-2-yl)but-3-enyl bromide
• 英文别名: 4,4-bis(thien-2-yl)but-3-enyl bromide；2-(4-Bromo-1-thiophen-2-ylbut-1-enyl)thiophene
• CAS: 109857-80-9
• 化学式: C₁₂H₁₁BrS₂
• 分子量: 299.255
• InChiKey: ONSWUWFMBBJGMK-UHFFFAOYSA-N

物化性质

• 沸点：
  409.5±45.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-di(thien-2-yl)but-3-enyl bromide 在 sodium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 48.0h， 生成 N-(4,4-di(thien-2-yl)but-3-enyl)nipecotic 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：

  双(2-噻吩)酮 在 氢溴酸 、 magnesium 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 生成 4,4-di(thien-2-yl)but-3-enyl bromide
  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.

  具有在4-位置中可选择地取代的呋喃基、噻吩基、吡啶基和/或吡咯基的1-氨基丁-3-烯衍生物，在1-位置具有3-羧基哌啶-1-基、3-羧基四氢吡啶-1-基或3-羧基甲基吡咯烷-1-基，可以增强GABA能神经传导。
• [EN] AMINO ACID DERIVATIVES
  申请人：NOVO INDUSTRI A/S

  公开号：WO1987000171A1

  公开（公告）日：1987-01-15

  (EN) 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.(FR) Des dérivés de 1-aminobut-3-ène ayant furanyle, thiényle, pyridyle et/ou pyrrolyle éventuellement substitués en position 4 et 3-carboxypiperidine-1-yle, 3-carboxytétrahydropyride-1-yle ou 3-carboxyméthylpyrrolidine-1-yle éventuellement substitués en position 1activent la neurotransmission par l'acide $g(g)-aminobutyrique.

  (中文) 在1-氨基丁-3-烯衍生物的4位上，可以选择性地取代呋喃基，噻吩基，吡啶基和/或吡咯基，在1位上取代3-羧基哌啶-1-基，3-羧基四氢吡啶-1-基或3-羧基甲基吡咯烷基，可以增强GABA能神经递质的传递。 （法语）在4位上具有可选择的取代呋喃基，噻吩基，吡啶基和/或吡咯基的1-氨基丁-3-烯衍生物，以及在1位上具有可选择的取代3-羧基哌啶-1-基，3-羧基四氢吡啶-1-基或3-羧基甲基吡咯烷基的衍生物，可以激活GABA能神经递质的传递。
• AMINO ACID DERIVATIVES
  申请人：NOVO NORDISK A/S

  公开号：EP0236342B1

  公开（公告）日：1991-09-11
• US5010090A
  申请人：——

  公开号：US5010090A

  公开（公告）日：1991-04-23