2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-1-benzopyrylium chloride | 121011-56-1

• 分子结构分类: 有机化合物
• 英文名称: 2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-1-benzopyrylium chloride
• 英文别名: 4-(7-methoxy-3-phenylchromenylium-2-yl)phenol;chloride
• CAS: 121011-56-1
• 化学式: C₂₂H₁₇O₃*Cl
• 分子量: 364.828
• InChiKey: NNIKMUXYGCNTOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  40.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-1-benzopyrylium chloride 在 盐酸 、 双氧水 、 吡啶盐酸盐 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 [6-hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]phenylmethanone
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 苄基-4-羟基苯酮 在 盐酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以5.4 g的产率得到2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-1-benzopyrylium chloride
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006

文献信息

• DURANI, NEELAM;JAIN, RAKA;SAEED, ASHRAF;DIKSHIT, DINESH K.;DURANI, SUSHEE+, J. MED. CHEM., 32,(1989) N, C. 1700-1707
  作者：DURANI, NEELAM、JAIN, RAKA、SAEED, ASHRAF、DIKSHIT, DINESH K.、DURANI, SUSHEE+

  DOI：——

  日期：——