4-Chlorocarbonyl-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester | 288398-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-Chlorocarbonyl-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester
• CAS: 288398-61-8
• 化学式: C₈H₇ClO₃S₂
• 分子量: 250.727
• InChiKey: WIWYFLVLBANGER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Chlorocarbonyl-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester 在 三甲基铝 、 氯化铵 作用下， 以 丙酮 、 甲苯 、 乙腈 为溶剂， 生成 4-[2-(3,4,5-trimethoxyphenyl)aminothiazol-4-yl]-5-methylthiothiophene-2-carboxamidine
  参考文献：
  名称：

  Synthesis of thiophene-2-carboxamidines containing 2-amino-thiazoles and their biological evaluation as urokinase inhibitors

  摘要：

  The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino- 1,3-thiazolyl]-thiophene-2-carboxamidine is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00102-0
• 作为产物：
  描述：

  5-(methoxycarbonyl)-2-methylthiothiophene-3-carboxylic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 4-Chlorocarbonyl-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of thiophene-2-carboxamidines containing 2-amino-thiazoles and their biological evaluation as urokinase inhibitors

  摘要：

  The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino- 1,3-thiazolyl]-thiophene-2-carboxamidine is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00102-0

文献信息

• Structure-Based design, synthesis and sAR of a novel series of thiopheneamidine urokinase plasminogen activator inhibitors
  作者：Nalin L. Subasinghe、Carl Illig、James Hoffman、M.Jonathan Rudolph、Kenneth J. Wilson、Richard Soll、Troy Randle、David Green、Frank Lewandowski、Marie Zhang、Roger Bone、John Spurlino、Renee DesJarlais、Ingrid Deckman、Christopher J. Molloy、Carl Manthey、Zhau Zhou、Celia Sharp、Diane Maguire、Carl Crysler、Bruce Grasberger

  DOI：10.1016/s0960-894x(01)00247-5

  日期：2001.6

  The serine protease urokinase plasminogen activator (uPA) is thought to play a central role in tumor metastasis and angiogenesis. Molecular modeling studies suggest that 5-thiomethylthiopheneamidine inhibits uPA by binding at the S1 pocket of the active site. Further structure based elaboration of this residue resulted in a novel class of potent and selective inhibitors of uPA. (C) 2001 Elsevier Science Ltd. All rights reserved.