methyl 3-[4-(methylsulfanyl)phenyl]-1-benzothiophene-5-carboxylate | 1005206-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 3-[4-(methylsulfanyl)phenyl]-1-benzothiophene-5-carboxylate
• 英文别名: methyl 3-[4-(methylthio)phenyl]-1-benzothiophene-5-carboxylate；methyl 3-(4-methylsulfanylphenyl)-1-benzothiophene-5-carboxylate
• CAS: 1005206-98-3
• 化学式: C₁₇H₁₄O₂S₂
• 分子量: 314.429
• InChiKey: ZYDXMPJQIWUKFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-[4-(methylsulfanyl)phenyl]-1-benzothiophene-5-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以95%的产率得到3-[4-(methylsulfanyl)phenyl]-1-benzothiophene-5-carbohydrazide
  参考文献：
  名称：

  2-{3-[4-(Alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Glycogen Synthase Kinase-3β with Good Brain Permeability

  摘要：

  Glycogen synthase kinase 3beta (GSK-3beta) inhibition is expected to be a promising therapeutic approach for treating Alzheimer's disease. Previously we reported a series of 1,3,4-oxadiazole derivatives as potent and highly selective GSK-3beta inhibitors, however, the representative compounds 1a,b showed poor pharmacokinetic profiles. Efforts were made to address this issue by reducing molecular weight and lipophilicity, leading to the identification of oxadiazole derivatives containing a sulfinyl group, (S)-9b and (S)-9c. These compounds exhibited not only highly selective and potent inhibitory activity against GSK-3beta but also showed good pharmacokinetic profiles including favorable BBB penetration. In addition, (S)-9b and (S)-9c given orally to mice significantly inhibited cold water stress-induced tau hyperphosphorylation in mouse brain.

  DOI：

  10.1021/jm900647e
• 作为产物：
  描述：

  methyl 3-bromobenzo[b]thiophene-5-carboxylate 、 4-甲硫基苯硼酸 以the title compound (yield 76%) was obtained as colorless crystals的产率得到methyl 3-[4-(methylsulfanyl)phenyl]-1-benzothiophene-5-carboxylate
  参考文献：
  名称：

  GSK-3β inhibitor

  摘要：

  为了提供一种含有噁唑烷化合物或其盐或前药的GSK-3β抑制剂，该抑制剂可用作GSK-3β相关病理或疾病的预防或治疗剂，本发明提供了一种包含式（I）所表示的化合物的GSK-3β抑制剂：其中每个符号如规范中所定义，或其盐或前药。

  公开号：

  US08492378B2

文献信息

• GSK-3BETAINHIBITOR
  申请人：Itoh Fumio

  公开号：US20100069381A1

  公开（公告）日：2010-03-18

  For the purpose of providing a GSK-3β inhibitor containing an oxadiazole compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof.

  为了提供一种含有噁二唑化合物或其盐或其前药的GSK-3β抑制剂，用作GSK-3β相关病理或疾病的预防或治疗剂，本发明提供了一种含有由以下式（I）表示的化合物的GSK-3β抑制剂： 其中每个符号如规范中定义，或其盐或其前药。
• GSK-3β inhibitor
  申请人：Itoh Fumio

  公开号：US08492378B2

  公开（公告）日：2013-07-23

  For the purpose of providing a GSK-3β inhibitor containing an oxadiazole compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof.

  为了提供一种含有噁唑烷化合物或其盐或前药的GSK-3β抑制剂，该抑制剂可用作GSK-3β相关病理或疾病的预防或治疗剂，本发明提供了一种包含式（I）所表示的化合物的GSK-3β抑制剂：其中每个符号如规范中所定义，或其盐或前药。
• US8492378B2
  申请人：——

  公开号：US8492378B2

  公开（公告）日：2013-07-23
• 2-{3-[4-(Alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Glycogen Synthase Kinase-3β with Good Brain Permeability
  作者：Morihisa Saitoh、Jun Kunitomo、Eiji Kimura、Hiroki Iwashita、Yumiko Uno、Tomohiro Onishi、Noriko Uchiyama、Tomohiro Kawamoto、Toshimasa Tanaka、Clifford D. Mol、Douglas R. Dougan、Garret P. Textor、Gyorgy P. Snell、Masayuki Takizawa、Fumio Itoh、Masakuni Kori

  DOI：10.1021/jm900647e

  日期：2009.10.22

  Glycogen synthase kinase 3beta (GSK-3beta) inhibition is expected to be a promising therapeutic approach for treating Alzheimer's disease. Previously we reported a series of 1,3,4-oxadiazole derivatives as potent and highly selective GSK-3beta inhibitors, however, the representative compounds 1a,b showed poor pharmacokinetic profiles. Efforts were made to address this issue by reducing molecular weight and lipophilicity, leading to the identification of oxadiazole derivatives containing a sulfinyl group, (S)-9b and (S)-9c. These compounds exhibited not only highly selective and potent inhibitory activity against GSK-3beta but also showed good pharmacokinetic profiles including favorable BBB penetration. In addition, (S)-9b and (S)-9c given orally to mice significantly inhibited cold water stress-induced tau hyperphosphorylation in mouse brain.