2-carboxymethylmercapto-3-(4-bromobenzoyl)propionic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-carboxymethylmercapto-3-(4-bromobenzoyl)propionic acid
• 英文别名: 4-(4-Bromophenyl)-2-(carboxymethylsulfanyl)-4-oxobutanoic acid
• 化学式: C₁₂H₁₁BrO₅S
• 分子量: 347.186
• InChiKey: ABTRMPBSZSUHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-carboxymethylmercapto-3-(4-bromobenzoyl)propionic acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到4-carboxymethyl-mercaptan-6-(4-bromophenyl)-2,3,4,5-tetrahydro-3(2H)-pyridazin-3-one
  参考文献：
  名称：

  El-Hashash; El-Sayed; El-Kady, Egyptian Journal of Chemistry, 2008, vol. 51, # 1, p. 103 - 112

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-4-(4-溴苯基)-4-氧代丁2-烯酸 、 巯基乙酸 以 甲醇 为溶剂， 以86%的产率得到2-carboxymethylmercapto-3-(4-bromobenzoyl)propionic acid
  参考文献：
  名称：

  2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Selectively Suppressed Proliferation of Neoplastic Human HeLa Cells. A SAR/QSAR Study

  摘要：

  A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 mu M/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations (< 2 mu M/L). The most active compounds exert lower cytotoxicity toward healthy human peripheral blood mononuclear cells (PBMC and PBMC+PHA) (selectivity indexes > 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.

  DOI：

  10.1021/jm0502889

文献信息

• 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Selectively Suppressed Proliferation of Neoplastic Human HeLa Cells. A SAR/QSAR Study
  作者：Branko J. Drakulić、Zorica D. Juranić、Tatjana P. Stanojković、Ivan O. Juranić

  DOI：10.1021/jm0502889

  日期：2005.8.1

  A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 mu M/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations (< 2 mu M/L). The most active compounds exert lower cytotoxicity toward healthy human peripheral blood mononuclear cells (PBMC and PBMC+PHA) (selectivity indexes > 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.
• 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Suppressed Survival of Neoplastic Human HeLa Cells: A QSAR Study
  作者：Branko J. Drakulić、Zorica D. Juranić、Ivan O. Juranić

  DOI：10.1080/10426500590913294

  日期：2005.3.2
• El-Hashash; El-Sayed; El-Kady, Egyptian Journal of Chemistry, 2008, vol. 51, # 1, p. 103 - 112
  作者：El-Hashash、El-Sayed、El-Kady、Mohamed

  DOI：——

  日期：——