3-苯基-2-[4-(2-哌啶-1-基乙氧基)苯基]-2H-苯并吡喃-7-醇 | 130064-33-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3-苯基-2-[4-(2-哌啶-1-基乙氧基)苯基]-2H-苯并吡喃-7-醇
• 英文名称: 2-<4-(2-piperidinoethoxy)phenyl>-3-phenyl-7-hydroxy-2H-1-benzopyran
• 英文别名: 2-(4-(2-Piperidinoethoxy)phenyl)-7-hydroxy-2H-1-benzopyran；3-phenyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2H-chromen-7-ol
• CAS: 130064-33-4
• 化学式: C₂₈H₂₉NO₃
• 分子量: 427.543
• InChiKey: MYRIWUNKVOHSEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-<2-hydroxy-4-<(tetrahydropyran-2-yl)oxy>phenyl>-2-phenylethanone 在 哌啶 、 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 反应 42.33h， 生成 3-苯基-2-[4-(2-哌啶-1-基乙氧基)苯基]-2H-苯并吡喃-7-醇
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Phenolic analogs of 2,3-diaryl-2H-1-benzopyrans

  摘要：

  Phenolic analogues of 2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran (1), a novel antiestrogen, were synthesized and evaluated for their structure-activity relationship. Incorporation of OH at position 7 was found to improve receptor affinity of the benzopyran while having no effect on its action as an antagonist. Similar substitution of 2-phenyl as well potentiated receptor affinity as well as antagonist activity of the prototype. The monophenol 19 and the diphenol 25 were thus found to be good receptor ligands, devoid of estrogen agonist activity and associated with marked antiestrogenic activity of comparable order. Both caused nearly complete inhibition of the estradiol stimulated uterine growth in rats as well as mice and were thus found to be better antiestrogens than tamoxifen, trioxifen, and LY-117018. A binding-site model for estrogen receptor rationalizing the structure-activity relationship of benzopyrans in relation to that of the triarylethylene and the triarylpropenone antiestrogens has been discussed.

  DOI：

  10.1021/jm00174a020