methyl 3-(ethoxycarbonylmethoxy)-5-chlorothieno[3,2-b][1]benzothiophene-2-carboxylate | 881033-99-4

• 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-(ethoxycarbonylmethoxy)-5-chlorothieno[3,2-b][1]benzothiophene-2-carboxylate
• 英文别名: 7-chloro-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester；methyl 5-chloro-3-(2-ethoxy-2-oxoethoxy)thieno[3,2-b][1]benzothiole-2-carboxylate
• CAS: 881033-99-4
• 化学式: C₁₆H₁₃ClO₅S₂
• 分子量: 384.861
• InChiKey: GQXMLVHBHHUMBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-(ethoxycarbonylmethoxy)-5-chlorothieno[3,2-b][1]benzothiophene-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以65%的产率得到1-Carboxymethoxy-7-chloro-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid
  参考文献：
  名称：

  Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors

  摘要：

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.

  DOI：

  10.1016/j.bmc.2005.11.005
• 作为产物：
  描述：

  7-chloro-3-hydroxybenzo[b]thiophene-2-carboxylic acid methyl ester 在 三乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 methyl 3-(ethoxycarbonylmethoxy)-5-chlorothieno[3,2-b][1]benzothiophene-2-carboxylate
  参考文献：
  名称：

  Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors

  摘要：

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.

  DOI：

  10.1016/j.bmc.2005.11.005

文献信息

• PTP1b inhibitors
  申请人：Lee Jinbo

  公开号：US20060135488A1

  公开（公告）日：2006-06-22

  This invention relates to modulating (e.g., inhibiting) protein tyrosine phosphatase 1B (PTP1B).

  这项发明涉及调节（例如，抑制）蛋白酪氨酸磷酸酶1B（PTP1B）。
• US7674822B2
  申请人：——

  公开号：US7674822B2

  公开（公告）日：2010-03-09
• Bicyclic and tricyclic thiophenes as protein tyrosine phosphatase 1B inhibitors
  作者：A.F. Moretto、S.J. Kirincich、W.X. Xu、M.J. Smith、Z.-K. Wan、D.P. Wilson、B.C. Follows、E. Binnun、D. Joseph-McCarthy、K. Foreman、D.V. Erbe、Y.L. Zhang、S.K. Tam、S.Y. Tam、J. Lee

  DOI：10.1016/j.bmc.2005.11.005

  日期：2006.4

  A novel pyridothiophene inhibitor of PTP1B was discovered by rational screening of phosphotyrosine mimics at high micromolar concentrations. The potency of this lead compound has been improved significantly by medicinal chemistry guided by X-ray crystallography and molecular modeling. Excellent consistency has been observed between structure-activity relationships and structural information from PTP1B-inhibitor complexes.