methyl 3-[5-(4-isobutoxybenzoyl)-2-propoxyphenyl]propionate | 874204-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-[5-(4-isobutoxybenzoyl)-2-propoxyphenyl]propionate
• 英文别名: Methyl 3-[5-[4-(2-methylpropoxy)benzoyl]-2-propoxyphenyl]propanoate
• CAS: 874204-79-2
• 化学式: C₂₄H₃₀O₅
• 分子量: 398.499
• InChiKey: KZFTUAJEVHMFOI-UHFFFAOYSA-N

物化性质

• 沸点：
  526.2±50.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-[5-(4-isobutoxybenzoyl)-2-propoxyphenyl]propionate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以94%的产率得到3-[5-(4-Isobutoxy-benzoyl)-2-propoxy-phenyl]-propionic acid
  参考文献：
  名称：

  Discovery of Nonpeptidic Small-Molecule AP-1 Inhibitors:  Lead Hopping Based on a Three-Dimensional Pharmacophore Model

  摘要：

  We designed and synthesized small-molecule activator protein-1 (AP-1) inhibitors based on a three-dimensional (3D) pharmacophore model that we had previously derived from a cyclic decapeptide exhibiting AP-1 inhibitory activity. New AP-1 inhibitors with a 1-thia-4-azaspiro[4.5]decane or a benzophenone scaffold, which inhibit the DNA-binding and transactivation activities of AP-1, were discovered using a "lead hopping" procedure. An additional investigation of the benzophenone analogues confirmed the reliability of the pharmacophore model, its utility to discover AP-1 inhibitors, and the potency of the benzophenone derivatives as a lead series.

  DOI：

  10.1021/jm050550d
• 作为产物：
  描述：

  isobutyl 3-(2-isobutoxyphenyl)propionate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 三氯化铝 、 草酰氯 、 偶氮二甲酸二异丙酯 、 双氧水 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.5h， 生成 methyl 3-[5-(4-isobutoxybenzoyl)-2-propoxyphenyl]propionate
  参考文献：
  名称：

  Discovery of Nonpeptidic Small-Molecule AP-1 Inhibitors:  Lead Hopping Based on a Three-Dimensional Pharmacophore Model

  摘要：

  We designed and synthesized small-molecule activator protein-1 (AP-1) inhibitors based on a three-dimensional (3D) pharmacophore model that we had previously derived from a cyclic decapeptide exhibiting AP-1 inhibitory activity. New AP-1 inhibitors with a 1-thia-4-azaspiro[4.5]decane or a benzophenone scaffold, which inhibit the DNA-binding and transactivation activities of AP-1, were discovered using a "lead hopping" procedure. An additional investigation of the benzophenone analogues confirmed the reliability of the pharmacophore model, its utility to discover AP-1 inhibitors, and the potency of the benzophenone derivatives as a lead series.

  DOI：

  10.1021/jm050550d

文献信息

• Discovery of Nonpeptidic Small-Molecule AP-1 Inhibitors:  Lead Hopping Based on a Three-Dimensional Pharmacophore Model
  作者：Keiichi Tsuchida、Hisaaki Chaki、Tadakazu Takakura、Hironori Kotsubo、Tadashi Tanaka、Yukihiko Aikawa、Shunichi Shiozawa、Shuichi Hirono

  DOI：10.1021/jm050550d

  日期：2006.1.1

  We designed and synthesized small-molecule activator protein-1 (AP-1) inhibitors based on a three-dimensional (3D) pharmacophore model that we had previously derived from a cyclic decapeptide exhibiting AP-1 inhibitory activity. New AP-1 inhibitors with a 1-thia-4-azaspiro[4.5]decane or a benzophenone scaffold, which inhibit the DNA-binding and transactivation activities of AP-1, were discovered using a "lead hopping" procedure. An additional investigation of the benzophenone analogues confirmed the reliability of the pharmacophore model, its utility to discover AP-1 inhibitors, and the potency of the benzophenone derivatives as a lead series.