5-(cyclohexylmethoxy)-3-(((2-hydroxyethyl)(phenyl)amino)methyl)-4H-chromen-4-one | 1397956-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-(cyclohexylmethoxy)-3-(((2-hydroxyethyl)(phenyl)amino)methyl)-4H-chromen-4-one
• 英文别名: 5-(cyclohexylmethoxy)-3-[[N-(2-hydroxyethyl)anilino]methyl]chromen-4-one
• CAS: 1397956-72-7
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: MFYXTOVZWFWRJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(cyclohexylmethoxy)-4-oxo-4H-chromene-3-carbaldehyde 、 N-苯基乙醇胺 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以35%的产率得到5-(cyclohexylmethoxy)-3-(((2-hydroxyethyl)(phenyl)amino)methyl)-4H-chromen-4-one
  参考文献：
  名称：

  Novel interleukin-5 inhibitors based on hydroxyethylaminomethyl-4H-chromen-4-one scaffold

  摘要：

  Hydroxyethylaminomethyl-4H-chromenones were previously discovered as fairly strong IL-5 inhibitor. For determination of detail structure activity relationship, N-substituted hydroxyethylaminomethyl-chromenones 4a-n were prepared and evaluated for their IL-5 inhibitory activity. Shifting the hydrophobic group to nitrogen from 1-position of hydroxyethylamino moiety of hydroxyethylaminomethyl-4H-chromenones enhances the activity. The increment in bulkiness or hydrophobicity of alkyl side chain at amino group increases the activity. The same level of activity of 5-(cyclohexylmethoxy)-3-(N-benzyl-2-hydroxyethylaminomethyl)-4H-chromenone analogs regardless of hydrophobic or hydrophilic substituents at 4th position of phenyl ring might infer the existence of tunnel structure in the putative receptor for accepting these side chains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.006

文献信息

• Novel interleukin-5 inhibitors based on hydroxyethylaminomethyl-4H-chromen-4-one scaffold
  作者：Cheonik Joo、Eeda Venkateswararao、Ki-Cheul Lee、Vinay K. Sharma、Min-Sik Kyung、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmc.2012.08.006

  日期：2012.10

  Hydroxyethylaminomethyl-4H-chromenones were previously discovered as fairly strong IL-5 inhibitor. For determination of detail structure activity relationship, N-substituted hydroxyethylaminomethyl-chromenones 4a-n were prepared and evaluated for their IL-5 inhibitory activity. Shifting the hydrophobic group to nitrogen from 1-position of hydroxyethylamino moiety of hydroxyethylaminomethyl-4H-chromenones enhances the activity. The increment in bulkiness or hydrophobicity of alkyl side chain at amino group increases the activity. The same level of activity of 5-(cyclohexylmethoxy)-3-(N-benzyl-2-hydroxyethylaminomethyl)-4H-chromenone analogs regardless of hydrophobic or hydrophilic substituents at 4th position of phenyl ring might infer the existence of tunnel structure in the putative receptor for accepting these side chains. (C) 2012 Elsevier Ltd. All rights reserved.