2'-Hydroxy-5'-chlor-4-brom-chalkon | 15934-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-Hydroxy-5'-chlor-4-brom-chalkon
• 英文别名: 3-(4-Bromophenyl)-1-(5-chloro-2-hydroxyphenyl)-2-propen-1-one；3-(4-bromophenyl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one
• CAS: 15934-59-5
• 化学式: C₁₅H₁₀BrClO₂
• 分子量: 337.6
• InChiKey: OOFMASRZPRVDLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.0±45.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-Hydroxy-5'-chlor-4-brom-chalkon 、 3-氨基-1,2,4-三氮唑 生成 (+/-)-2-[7-(4-bromophenyl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-4-chlorophenol
  参考文献：
  名称：

  Discovery and Optimization of Chromenotriazolopyrimidines as Potent Inhibitors of the Mouse Double Minute 2−Tumor Protein 53 Protein−Protein Interaction

  摘要：

  Tumor protein 53 (p53) is a critical regulator of cell cycle and apoptosis that is frequently disabled in human tumors. In many tumor types, p53 is deleted or mutated, but in others p53 is inactivated by overexpression or amplification of its negative regulator mouse double minute 2 (MDM2). A high-throughput screening effort identified 6,7-bis(4-bromophenyl)-7,12-dihydro-6H-chromeno[4,3-d]-[1,2,4]triazolo[1,5-a]pyrimidine as a potent inhibitor of the MDM2-p53 protein-protein interaction. This screening hit was found to be chemically unstable and difficult to handle due to poor DMSO solubility. Co-crystallization with the target protein helped to direct further optimization and provided a tractable lead series of novel MDM2-p53 inhibitors. In cellular assays, these compounds were shown to upregulate p53 protein levels and p53 signaling and to cause p53-dependent inhibition of proliferation and apoptosis.

  DOI：

  10.1021/jm900681h
• 作为产物：
  描述：

  乙酸-4-氯苯酯 在 sodium hydroxide 、 三氯化铝 作用下， 生成 2'-Hydroxy-5'-chlor-4-brom-chalkon
  参考文献：
  名称：

  Chlor-hydroxychalkone

  摘要：

  DOI：

  10.1007/bf00904270

文献信息

• Chlor-hydroxychalkone
  作者：S. H. Dandegaonker、S. G. Shet

  DOI：10.1007/bf00904270

  日期：——
• Discovery and Optimization of Chromenotriazolopyrimidines as Potent Inhibitors of the Mouse Double Minute 2−Tumor Protein 53 Protein−Protein Interaction
  作者：John G. Allen、Matthew P. Bourbeau、G. Erich Wohlhieter、Michael D. Bartberger、Klaus Michelsen、Randall Hungate、Robert C. Gadwood、Rick D. Gaston、Bruce Evans、Larry W. Mann、Michael E. Matison、Stephen Schneider、Xin Huang、Dongyin Yu、Paul S. Andrews、Andreas Reichelt、Alexander M. Long、Peter Yakowec、Evelyn Y. Yang、Tani Ann Lee、Jonathan D. Oliner

  DOI：10.1021/jm900681h

  日期：2009.11.26

  Tumor protein 53 (p53) is a critical regulator of cell cycle and apoptosis that is frequently disabled in human tumors. In many tumor types, p53 is deleted or mutated, but in others p53 is inactivated by overexpression or amplification of its negative regulator mouse double minute 2 (MDM2). A high-throughput screening effort identified 6,7-bis(4-bromophenyl)-7,12-dihydro-6H-chromeno[4,3-d]-[1,2,4]triazolo[1,5-a]pyrimidine as a potent inhibitor of the MDM2-p53 protein-protein interaction. This screening hit was found to be chemically unstable and difficult to handle due to poor DMSO solubility. Co-crystallization with the target protein helped to direct further optimization and provided a tractable lead series of novel MDM2-p53 inhibitors. In cellular assays, these compounds were shown to upregulate p53 protein levels and p53 signaling and to cause p53-dependent inhibition of proliferation and apoptosis.