isobutyl 3-(2-isobutoxyphenyl)propionate | 269082-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: isobutyl 3-(2-isobutoxyphenyl)propionate
• 英文别名: 2-Methylpropyl 3-[2-(2-methylpropoxy)phenyl]propanoate
• CAS: 269082-00-0
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: MXMATQXUTFLMDI-UHFFFAOYSA-N

物化性质

• 沸点：
  352.6±17.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 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 、 乙腈 为溶剂， 反应 14.5h， 生成 methyl 3-[2-hydroxy-5-(4-propoxybenzoyl)phenyl]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
• 作为产物：
  描述：

  3-(2-羟基苯基)丙酸 、 溴代异丁烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到isobutyl 3-(2-isobutoxyphenyl)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.