4-Brom-5'-methyl-2'-hydroxy-chalkon | 16635-11-3

• 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: 4-Brom-5'-methyl-2'-hydroxy-chalkon
• 英文别名: 3-(4-Bromophenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one；3-(4-bromophenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
• CAS: 16635-11-3
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: XIPRBIIIPOOPMM-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  469.2±45.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-Brom-5'-methyl-2'-hydroxy-chalkon 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以68%的产率得到2-(5-(4-bromophenyl)-4,5-dihydroisoxazol-3-yl)-4-methylphenol
  参考文献：
  名称：

  Basawaraj, Raga; Hassappa, Ravi; Chillargi, Neelavathi, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 253 - 256

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 、 对溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以70%的产率得到4-Brom-5'-methyl-2'-hydroxy-chalkon
  参考文献：
  名称：

  Basawaraj, Raga; Hassappa, Ravi; Chillargi, Neelavathi, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 253 - 256

  摘要：

  DOI：

文献信息

• 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.