1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]吡咯烷 | 130378-74-4

• 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: 1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]吡咯烷
• 英文名称: 2-(4-(2-Pyrrolidinoethoxy)phenyl)-3-phenyl-2H-1-benzopyran
• 英文别名: 1-[2-[4-(3-phenyl-2H-chromen-2-yl)phenoxy]ethyl]pyrrolidine
• CAS: 130378-74-4
• 化学式: C₂₇H₂₇NO₂
• 分子量: 397.517
• InChiKey: KWBXGHFQOFIZKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-羟基苯基)-2-苯基乙酮 在 哌啶 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 反应 72.0h， 生成 1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]吡咯烷
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans

  摘要：

  A series of 2,3-diaryl-1-benzopyran analogues substituted at position 4 of 2-phenyl with a hydroxy or pyrrolidinoethoxy residue were synthesized as models for (E)-triarylpropenones constrained in the s-trans conformation. The prototypes, belonging to five chemical series, were evaluated for their estrogen receptor affinity and for estrogen agonist-antagonist activities. The 4H-1-benzopyran-4-one, the 2,3-dihydro-4H-1-benzopyran-4-one, the 4H-1-benzopyran, and the 2,3-dihydro-1-benzopyran derivatives were found to be inactive or only marginally activate as receptor ligands or estrogen agonists-antagonists. In the 2H-1-benzopyran category the parent phenol was also inactive whereas the basic ethers 16 and 26 were modest receptor ligands while being quite active as antiestrogens. In a comparative study the benzopyran 16 was found to be more effective antiestrogen than tamoxifen while being as effective as LY-117018. The benzopyrans have thus emerged as a new class of potent antiestrogens.

  DOI：

  10.1021/jm00174a018

文献信息

• SAEED, A.;SHARMA, A. P.;DURANI, N., J. MED. CHEM., 33,(1990) N2, C. 3210-3216
  作者：SAEED, A.、SHARMA, A. P.、DURANI, N.

  DOI：——

  日期：——
• Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans
  作者：Ashraf Saeed、Arun P. Sharma、Neelam Durani、Raka Jain、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00174a018

  日期：1990.12

  A series of 2,3-diaryl-1-benzopyran analogues substituted at position 4 of 2-phenyl with a hydroxy or pyrrolidinoethoxy residue were synthesized as models for (E)-triarylpropenones constrained in the s-trans conformation. The prototypes, belonging to five chemical series, were evaluated for their estrogen receptor affinity and for estrogen agonist-antagonist activities. The 4H-1-benzopyran-4-one, the 2,3-dihydro-4H-1-benzopyran-4-one, the 4H-1-benzopyran, and the 2,3-dihydro-1-benzopyran derivatives were found to be inactive or only marginally activate as receptor ligands or estrogen agonists-antagonists. In the 2H-1-benzopyran category the parent phenol was also inactive whereas the basic ethers 16 and 26 were modest receptor ligands while being quite active as antiestrogens. In a comparative study the benzopyran 16 was found to be more effective antiestrogen than tamoxifen while being as effective as LY-117018. The benzopyrans have thus emerged as a new class of potent antiestrogens.