5-(Cyclohexylmethoxy)-3-[3-oxo-3-[4-(trifluoromethyl)phenyl]propyl]chromen-4-one | 1431135-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(Cyclohexylmethoxy)-3-[3-oxo-3-[4-(trifluoromethyl)phenyl]propyl]chromen-4-one
• CAS: 1431135-75-9
• 化学式: C₂₆H₂₅F₃O₄
• 分子量: 458.477
• InChiKey: ZRHLEOKFPHJVMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(Cyclohexylmethoxy)-3-[3-oxo-3-[4-(trifluoromethyl)phenyl]propyl]chromen-4-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以88%的产率得到5-(Cyclohexylmethoxy)-3-[3-hydroxy-3-[4-(trifluoromethyl)phenyl]propyl]chromen-4-one
  参考文献：
  名称：

  Design and synthesis of novel chromenone derivatives as interleukin-5 inhibitors

  摘要：

  A novel series of chromenone analogs were synthesized and evaluated for their inhibitory activity against interleukin-5. Among them 5-(cyclohexylmethoxy)-3-[3-hydroxy-3-(4-hydroxyphenyl)propyl]-4H-chromen-4-one (9b, 94% inhibition at 30 mu M, IC50 = 4.0 mu M) and 5-(cyclohexylmethoxy)-3-[3-hydroxy-3-(4-methoxyphenyl)propyl]-4H-chromen-4-one (9c, 94% inhibition at 30 mu M, IC50 = 6.5 mu M) showed the most potent activity. According to the SAR studies introduction of propanone unit in between chromenone and ring B as in 5-(cyclohexylmethoxy)-3-[3-(4-phenyl)-3-oxopropyl]-4H-chromen-4-ones (8) moderately increased the activity. However, the reduction of these propanones 8 to propanols 9 remarkably enhanced the activity. A small substituent at position 4 of ring B in 9, especially with hydrogen bonding capability, provides favorable contribution. Disappearance of IL-5 inhibitory activity upon saturation of chroman-4-one of 9 to chroman-4-ones 10 proves the critical importance of planar chromen-4-one unit of this scaffold in the IL-5 inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.037
• 作为产物：
  描述：

  在 palladium on carbon 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以56.1%的产率得到5-(Cyclohexylmethoxy)-3-[3-oxo-3-[4-(trifluoromethyl)phenyl]propyl]chromen-4-one
  参考文献：
  名称：

  Design and synthesis of novel chromenone derivatives as interleukin-5 inhibitors

  摘要：

  A novel series of chromenone analogs were synthesized and evaluated for their inhibitory activity against interleukin-5. Among them 5-(cyclohexylmethoxy)-3-[3-hydroxy-3-(4-hydroxyphenyl)propyl]-4H-chromen-4-one (9b, 94% inhibition at 30 mu M, IC50 = 4.0 mu M) and 5-(cyclohexylmethoxy)-3-[3-hydroxy-3-(4-methoxyphenyl)propyl]-4H-chromen-4-one (9c, 94% inhibition at 30 mu M, IC50 = 6.5 mu M) showed the most potent activity. According to the SAR studies introduction of propanone unit in between chromenone and ring B as in 5-(cyclohexylmethoxy)-3-[3-(4-phenyl)-3-oxopropyl]-4H-chromen-4-ones (8) moderately increased the activity. However, the reduction of these propanones 8 to propanols 9 remarkably enhanced the activity. A small substituent at position 4 of ring B in 9, especially with hydrogen bonding capability, provides favorable contribution. Disappearance of IL-5 inhibitory activity upon saturation of chroman-4-one of 9 to chroman-4-ones 10 proves the critical importance of planar chromen-4-one unit of this scaffold in the IL-5 inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.037