1-(4-Bromo-benzenesulfonyl)-cyclopropanecarboxylic acid methyl ester | 145348-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-Bromo-benzenesulfonyl)-cyclopropanecarboxylic acid methyl ester
• 英文别名: Cyclopropanecarboxylic acid, 1-((4-bromophenyl)sulfonyl)-, methyl ester；methyl 1-(4-bromophenyl)sulfonylcyclopropane-1-carboxylate
• CAS: 145348-25-0
• 化学式: C₁₁H₁₁BrO₄S
• 分子量: 319.176
• InChiKey: IPABBDLXSJIQEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-Bromo-benzenesulfonyl)-cyclopropanecarboxylic acid methyl ester 在 盐酸 、 四(三苯基膦)钯 、 sodium methylate 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 2-(4'-Chloro-biphenyl-4-sulfonyl)-4-phenylsulfanyl-butyric acid
  参考文献：
  名称：

  Synthesis and SAR of α-sulfonylcarboxylic acids as potent matrix metalloproteinase inhibitors

  摘要：

  A series of novel carboxylic acid-based alpha-sulfone MMP inhibitors have been synthesized and the in vitro enzyme SAR is discussed. A potential binding mode in the active site of the MMP-9 homology model was highlighted. These compounds are potent MMP-9 inhibitors and are selective over MMP-1. (c) 2006 Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.03.065
• 作为产物：
  描述：

  2-(4-Bromo-benzenesulfonyl)-4-(toluene-4-sulfonyloxy)-butyric acid methyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-Bromo-benzenesulfonyl)-cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and SAR of α-sulfonylcarboxylic acids as potent matrix metalloproteinase inhibitors

  摘要：

  A series of novel carboxylic acid-based alpha-sulfone MMP inhibitors have been synthesized and the in vitro enzyme SAR is discussed. A potential binding mode in the active site of the MMP-9 homology model was highlighted. These compounds are potent MMP-9 inhibitors and are selective over MMP-1. (c) 2006 Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.03.065

文献信息

• Synthesis and SAR of α-sulfonylcarboxylic acids as potent matrix metalloproteinase inhibitors
  作者：Yue-Mei Zhang、Xiaodong Fan、Bangping Xiang、Devraj Chakravarty、Robert Scannevin、Sharon Burke、Prabha Karnachi、Kenneth Rhodes、Paul Jackson

  DOI：10.1016/j.bmcl.2006.03.065

  日期：2006.6

  A series of novel carboxylic acid-based alpha-sulfone MMP inhibitors have been synthesized and the in vitro enzyme SAR is discussed. A potential binding mode in the active site of the MMP-9 homology model was highlighted. These compounds are potent MMP-9 inhibitors and are selective over MMP-1. (c) 2006 Elsevier Ltd.