(2E)-1-(3-Bromophenyl)-3-(2-chlorophenyl)prop-2-en-1-one | 1061342-80-0

• 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: (2E)-1-(3-Bromophenyl)-3-(2-chlorophenyl)prop-2-en-1-one
• 英文别名: (E)-1-(3-bromophenyl)-3-(2-chlorophenyl)prop-2-en-1-one
• CAS: 1061342-80-0
• 化学式: C₁₅H₁₀BrClO
• 分子量: 321.601
• InChiKey: MROFKUQZOLCZQH-CMDGGOBGSA-N

物化性质

• 熔点：
  175 °C(Solv: chloroform (67-66-3))
• 沸点：
  433.4±45.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-1-(3-Bromophenyl)-3-(2-chlorophenyl)prop-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (5S,7R)-5-(3-bromophenyl)-7-(2-chlorophenyl)-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Isoform-Selective and Stereoselective Inhibition of Hypoxia Inducible Factor-2

  摘要：

  Hypoxia inducible factor (HIF) transcription factors reside at the center of signaling pathways used by mammalian cells to sense and respond to low oxygen levels. While essential to maintain oxygen homeostasis, misregulation of HIF protein activity correlates with tumor development and metastasis. To provide artificial routes to target misregulated HIF activity, we identified small molecule antagonists of the HIF-2 transcription factor that bind an internal cavity within the C-terminal PAS domain of the HIF-2 alpha subunit. Here we describe a new class of chiral small molecule ligands that provide the highest affinity binding, the most effective, isoform-selective inhibition of HIP-2 in cells, and trigger the largest protein conformation changes reported to date. The current results further illuminate the molecular mechanism of HIF-2 antagonism and suggest additional routes to develop higher affinity and potency HIF-2 antagonists.

  DOI：

  10.1021/acs.jmedchem.5b00529
• 作为产物：
  描述：

  2-氯苯甲醛 、 3'-溴苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以54%的产率得到(2E)-1-(3-Bromophenyl)-3-(2-chlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Syntheses and evaluation of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline derivatives

  摘要：

  A variety of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline were obtained by the refluxing of 1-N-thiocarbamoyl 3,5-diphenyl-2-pyrazoline with 2,3-dichloroquinoxaline. The chemical structures of the compounds were elucidated by UV, IR, H-1 NMR, and C-13 NMR spectroscopy. The purity of the compounds was confirmed by their elemental analysis. The antiamoebic activity of these compounds was evaluated by microdilution method against HMI:IMSS strain of Entamoeba histolytica and the IC50 values were compared with the standard drug metronidazole. Some of the quinoxaline derivatives showed less IC50 values than metronidazole. To elucidate the toxic effect, MTT assay was performed using kidney epithelial cell line. The results showed that all the compounds are non-toxic. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.026

文献信息

• Syntheses and evaluation of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline derivatives
  作者：Asha Budakoti、Abdul R. Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.10.026

  日期：2008.8

  A variety of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline were obtained by the refluxing of 1-N-thiocarbamoyl 3,5-diphenyl-2-pyrazoline with 2,3-dichloroquinoxaline. The chemical structures of the compounds were elucidated by UV, IR, H-1 NMR, and C-13 NMR spectroscopy. The purity of the compounds was confirmed by their elemental analysis. The antiamoebic activity of these compounds was evaluated by microdilution method against HMI:IMSS strain of Entamoeba histolytica and the IC50 values were compared with the standard drug metronidazole. Some of the quinoxaline derivatives showed less IC50 values than metronidazole. To elucidate the toxic effect, MTT assay was performed using kidney epithelial cell line. The results showed that all the compounds are non-toxic. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Isoform-Selective and Stereoselective Inhibition of Hypoxia Inducible Factor-2
  作者：Thomas H. Scheuermann、Daniel Stroud、Christopher E. Sleet、Liela Bayeh、Cameron Shokri、Hanzhi Wang、Charles G. Caldwell、Jamie Longgood、John B. MacMillan、Richard K. Bruick、Kevin H. Gardner、Uttam K. Tambar

  DOI：10.1021/acs.jmedchem.5b00529

  日期：2015.8.13

  Hypoxia inducible factor (HIF) transcription factors reside at the center of signaling pathways used by mammalian cells to sense and respond to low oxygen levels. While essential to maintain oxygen homeostasis, misregulation of HIF protein activity correlates with tumor development and metastasis. To provide artificial routes to target misregulated HIF activity, we identified small molecule antagonists of the HIF-2 transcription factor that bind an internal cavity within the C-terminal PAS domain of the HIF-2 alpha subunit. Here we describe a new class of chiral small molecule ligands that provide the highest affinity binding, the most effective, isoform-selective inhibition of HIP-2 in cells, and trigger the largest protein conformation changes reported to date. The current results further illuminate the molecular mechanism of HIF-2 antagonism and suggest additional routes to develop higher affinity and potency HIF-2 antagonists.