3-(4'-carboxybenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene | 141563-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4'-carboxybenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene
• 英文别名: 4-[6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophene-3-carbonyl]benzoic acid
• CAS: 141563-39-5
• 化学式: C₂₂H₁₄O₅S
• 分子量: 390.416
• InChiKey: CLUVVTXMDRFWNE-UHFFFAOYSA-N

物化性质

• 沸点：
  726.9±60.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4'-carboxybenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene 在 N-甲基吗啉 、 二苯基膦叠氮化物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以15%的产率得到3-<(4'-azidocarbonyl)benzoyl>-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene
  参考文献：
  名称：

  Nonsteroidal estrogens bearing acyl azide functions: potential electrophilic and photoaffinity labeling agents for the estrogen receptor

  摘要：

  In an effort to develop novel affinity labeling agents for the estrogen receptor, we have synthesized two nonsteroidal ligands, a 1-aroyl-2-aryl tetralin system (1) and a 2-aryl-3-aroylbenzo[b]thiophene system (2). These agents, patterned after the Lilly antiestrogens trioxifene and LY 117018, respectively, embody acyl azide functions as part of a benzoyl chromophore. The acyl azide group has weak acylating activity, suitable for electrophilic affinity labeling, but this function is also photoreactive and, in its particular embodiment within these ligands, it could provide an efficient photochemical route to the highly reactive singlet acyl nitrene. The tetralin system (1) was prepared in nine steps from 6-methoxy-1-tetralone, and the benzothiophene system (2) was prepared in four steps from a known substituted benzo[b]thiophene precursor. In competitive binding assays, both compounds show reasonable binding affinity for the rat and lamb uterine estrogen receptor: estradiol = 100%, 1 = 3%, and 2 = 12%. When assayed by indirect receptor consumption assays, both compounds appear to have substantial capacity for irreversible binding (electrophilic reaction) with the receptor. This reactivity, which suggests that acylation of the receptor has occurred, is photoreversible. The nature of this ligand-receptor interaction is being investigated further.

  DOI：

  10.1016/0039-128x(92)90106-j
• 作为产物：
  描述：

  ethyl 4-(chlorocarbonyl)benzoate 在 sodium hydroxide 、 三氯化铝 、 三氟二甲基硫醚络合物 、 水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.25h， 生成 3-(4'-carboxybenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene
  参考文献：
  名称：

  Nonsteroidal estrogens bearing acyl azide functions: potential electrophilic and photoaffinity labeling agents for the estrogen receptor

  摘要：

  In an effort to develop novel affinity labeling agents for the estrogen receptor, we have synthesized two nonsteroidal ligands, a 1-aroyl-2-aryl tetralin system (1) and a 2-aryl-3-aroylbenzo[b]thiophene system (2). These agents, patterned after the Lilly antiestrogens trioxifene and LY 117018, respectively, embody acyl azide functions as part of a benzoyl chromophore. The acyl azide group has weak acylating activity, suitable for electrophilic affinity labeling, but this function is also photoreactive and, in its particular embodiment within these ligands, it could provide an efficient photochemical route to the highly reactive singlet acyl nitrene. The tetralin system (1) was prepared in nine steps from 6-methoxy-1-tetralone, and the benzothiophene system (2) was prepared in four steps from a known substituted benzo[b]thiophene precursor. In competitive binding assays, both compounds show reasonable binding affinity for the rat and lamb uterine estrogen receptor: estradiol = 100%, 1 = 3%, and 2 = 12%. When assayed by indirect receptor consumption assays, both compounds appear to have substantial capacity for irreversible binding (electrophilic reaction) with the receptor. This reactivity, which suggests that acylation of the receptor has occurred, is photoreversible. The nature of this ligand-receptor interaction is being investigated further.

  DOI：

  10.1016/0039-128x(92)90106-j

文献信息

• Nonsteroidal estrogens bearing acyl azide functions: potential electrophilic and photoaffinity labeling agents for the estrogen receptor
  作者：Kevin G. Pinney、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1016/0039-128x(92)90106-j

  日期：1992.5

  In an effort to develop novel affinity labeling agents for the estrogen receptor, we have synthesized two nonsteroidal ligands, a 1-aroyl-2-aryl tetralin system (1) and a 2-aryl-3-aroylbenzo[b]thiophene system (2). These agents, patterned after the Lilly antiestrogens trioxifene and LY 117018, respectively, embody acyl azide functions as part of a benzoyl chromophore. The acyl azide group has weak acylating activity, suitable for electrophilic affinity labeling, but this function is also photoreactive and, in its particular embodiment within these ligands, it could provide an efficient photochemical route to the highly reactive singlet acyl nitrene. The tetralin system (1) was prepared in nine steps from 6-methoxy-1-tetralone, and the benzothiophene system (2) was prepared in four steps from a known substituted benzo[b]thiophene precursor. In competitive binding assays, both compounds show reasonable binding affinity for the rat and lamb uterine estrogen receptor: estradiol = 100%, 1 = 3%, and 2 = 12%. When assayed by indirect receptor consumption assays, both compounds appear to have substantial capacity for irreversible binding (electrophilic reaction) with the receptor. This reactivity, which suggests that acylation of the receptor has occurred, is photoreversible. The nature of this ligand-receptor interaction is being investigated further.