3-Methylaminobenzothiophene-2-carboxylic acid methyl ester | 83716-04-5

• 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: 3-Methylaminobenzothiophene-2-carboxylic acid methyl ester
• 英文别名: Methyl 3-(methylamino)benzo[b]thiophene-2-carboxylate；methyl 3-(methylamino)-1-benzothiophene-2-carboxylate
• CAS: 83716-04-5
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: HEDBTMVEFOAHKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Methylaminobenzothiophene-2-carboxylic acid methyl ester 在 sodium ethanolate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.33h， 生成
  参考文献：
  名称：

  Scaffold hopping strategy to derive 4‐hydroxy‐1‐alkyl‐2‐oxo ‐1, 2‐dihydrothieno [2,3‐b:4,5‐b′] dipyridine‐3‐carbonylglycine derivatives as a novel hypoxia‐inducible factor prolyl hydroxylase domain inhibitor for the potential treatment of chronic kidney disease anemia

  摘要：

  AbstractDerivatives of 4‐hydroxy‐1‐alkyl‐2‐oxo‐1,2‐dihydrothieno[2,3‐b:4,5‐b′]dipyridine‐3‐carbonylglycine were developed as a novel hypoxia‐inducible factor prolyl hydroxylase domain (PHD) inhibitor. The chemical space of the tricyclic 4‐hydroxypyridinyl glycines was examined thoroughly during our optimization study. One of our most potent compounds 12ar exhibits superior enzymatic activity to the known PHD inhibitors that are in the late stage of clinical studies. The functional efficacy of our PHD inhibitors was confirmed via the increased level of erythropoietin (EPO) expression in a dose‐dependent manner in vitro.

  DOI：

  10.1002/bkcs.12652
• 作为产物：
  描述：

  2H-Benzothieno<3,2-d><1,3>oxazine-2,4(1H)-dione 在 sodium methylate 、 sodium hydride 作用下， 反应 6.0h， 生成 3-Methylaminobenzothiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Coppola, Gary M.; Hardtmann, Goetz E.; Pfister, Oskar R., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 717 - 720

  摘要：

  DOI：