2-(苯并[b]噻吩-7-基)乙酸 | 1468-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-(苯并[b]噻吩-7-基)乙酸
• 英文名称: benzo[b]thiophen-7-yl-acetic acid
• 英文别名: 7-Carboxymethyl-benzothiophen；Benzo[b]thiophen-7-yl-essigsaeure；Benzo[b]thiophene-7-acetic acid；2-(1-benzothiophen-7-yl)acetic acid
• CAS: 1468-80-0
• 化学式: C₁₀H₈O₂S
• 分子量: 192.238
• InChiKey: LXMVPQVMUHEPOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(苯并[b]噻吩-7-基)乙酸 、 N-[(4-chlorophenyl)methyl]-N,2-dimethylazetidine-2-carboxamide;hydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 1-(2-benzo[b]thiophen-7-yl-acetyl)-2-methyl-azetidine-2-carboxylic acid (4-chlorobenzyl)methylamide
  参考文献：
  名称：

  Discovery and Optimization of an Azetidine Chemical Series As a Free Fatty Acid Receptor 2 (FFA2) Antagonist: From Hit to Clinic

  摘要：

  FFA2, also called GPR43, is a G-protein coupled receptor for short chain fatty acids which is involved in the mediation of inflammatory responses. A class of azetidines was developed as potent FFA2 antagonists. Multiparametric optimization of early hits with moderate potency and suboptimal ADME properties led to the identification of several compounds with nanomolar potency on the receptor combined with excellent pharmacokinetic (PK) parameters. The most advanced compound, 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid 99 (GLPG0974), is able to inhibit acetate-induced neutrophil migration strongly in vitro and demonstrated ability to inhibit a neutrophil-based pharmacodynamic (PD) marker, CD11b activation-specific epitope [AE], in a human whole blood assay. All together, these data supported the progression of 99 toward next phases, becoming the first FFA2 antagonist to reach the clinic.

  DOI：

  10.1021/jm5012885
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 2-(苯并[b]噻吩-7-基)乙酸
  参考文献：
  名称：

  Matsuki; Fujieda, Nippon Kagaku Zasshi, 1967, vol. 88, p. 445

  摘要：

  DOI：

文献信息

• MacDowell; Greenwood, Journal of Heterocyclic Chemistry, 1965, vol. 2, p. 44,47
  作者：MacDowell、Greenwood

  DOI：——

  日期：——
• Kefford; Kelso, 1957, vol. 10, p. 80,82
  作者：Kefford、Kelso

  DOI：——

  日期：——