(4,5-Dibromo-thiophen-3-yloxy)-acetic acid | 96232-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4,5-Dibromo-thiophen-3-yloxy)-acetic acid
• 英文别名: 2-(4,5-Dibromothiophen-3-yloxy)acetic acid；2-(4,5-dibromothiophen-3-yl)oxyacetic acid
• CAS: 96232-57-4
• 化学式: C₆H₄Br₂O₃S
• 分子量: 315.97
• InChiKey: DIHNOAVMDSYCEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4,5-Dibromo-thiophen-3-yloxy)-acetic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 以62%的产率得到(2,4,5-Tribromo-thiophen-3-yloxy)-acetic acid
  参考文献：
  名称：

  Reactions with 3-Hydroxy-2-methoxycarbonylthiophene; I. Synthesis of 3-Thienyloxyacetic Acid and its (Nuclear) Chloro and Bromo Derivatives

  摘要：

  DOI：

  10.1055/s-1984-35467
• 作为产物：
  描述：

  4,5-dibromo-3-carboxymethoxy-thiophene-2-carboxylic acid 生成 (4,5-Dibromo-thiophen-3-yloxy)-acetic acid
  参考文献：
  名称：

  Reactions with 3-Hydroxy-2-methoxycarbonylthiophene; I. Synthesis of 3-Thienyloxyacetic Acid and its (Nuclear) Chloro and Bromo Derivatives

  摘要：

  DOI：

  10.1055/s-1984-35467

文献信息

• Probing acid replacements of thiophene PTP1B inhibitors
  作者：Zhao-Kui Wan、Bruce Follows、Steve Kirincich、Douglas Wilson、Eva Binnun、Weixin Xu、Diane Joseph-McCarthy、Junjun Wu、Michael Smith、Yan-Ling Zhang、May Tam、David Erbe、Steve Tam、Eddine Saiah、Jinbo Lee

  DOI：10.1016/j.bmcl.2007.02.043

  日期：2007.5

  The following account describes our systematic effort to replace one of the carboxylate groups of our diacid thiophene PTP1B inhibitors. Active hits were validated using enzymatic assays before pursuing efforts to improve the potency. Only when the C2 carboxylic acid was replaced with another ionizable functional group was reversible and competitive inhibition retained. Use of a tetrazole ring or 1,2,5-thiadiazolidine-3-one-1,1-dioxide as a carboxylate mimetic led to the discovery of two unique starting series that showed improved permeability (PAMPA) and potency of the order of 300 nM. The SAR from these efforts underscores some of the major challenges in developing small molecule inhibitors for PTP1B. (c) 2007 Elsevier Ltd. All rights reserved.
• CORRAL, C.;LISSAVETZKY, J., SYNTHESIS, BRD, 1984, N 10, 847-850
  作者：CORRAL, C.、LISSAVETZKY, J.

  DOI：——

  日期：——
• Reactions with 3-Hydroxy-2-methoxycarbonylthiophene; I. Synthesis of 3-Thienyloxyacetic Acid and its (Nuclear) Chloro and Bromo Derivatives
  作者：Carlos Corral、Jaime Lissavetzky

  DOI：10.1055/s-1984-35467

  日期：——