2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran | 130378-73-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran
• 英文别名: 2-[4-hydroxyphenyl]-3-phenyl-2H-1-benzopyran；4-(3-phenyl-2H-chromen-2-yl)phenol
• CAS: 130378-73-3
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: XYDAHTZKBPXZMI-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 30.5h， 生成 2-{4-[2-hydroxy-3-(n-butylamino)propoxy]phenyl}-3-phenyl-2H-1-benzopyran
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Effect of the side chain and its position on activity of 2,3-diaryl-2H-1-benzopyrans

  摘要：

  A series of 2,3-diaryl-2H-1-benzopyrans carrying a tertiary aminoethoxy chain at the ortho, meta, or para position of 2-phenyl or an alkyl at position 4 of the pyran ring were synthesized and evaluated for their affinity for estrogen receptor (ER) and for microsomal antiestrogen specific binding site and for their uterotrophic-antiuterotrophic activities in rodents. The analogues bearing the side chain at the para position of 2-phenyl were found to be active while those substituted at the meta and ortho positions were inactive as ER ligands as well as estrogen agonists-antagonists. Among para-substituted ethers, the 2-piperidinoethoxy analogue 5 was found to be a more effective antiestrogen than the corresponding pyrrolidino, dimethylamino, and related analogues. Incorporation of a methyl or an ethyl at C4 in the pyran nucleus was found to increase receptor affinity of the prototypes. The ethyl was also found to potentiate agonist activity of the prototype while abolishing its antagonist activity. The piperidino analogue 5 was found to be a better antiestrogen than tamoxifen as well as LY-117018 in rats as well as mice. The prototypes were also found to have high affinity for the microsomal antiestrogen specific binding sites. The benzopyrans have thus emerged as a new group of potent antiestrogens.

  DOI：

  10.1021/jm00174a019
• 作为产物：
  描述：

  对羟基苯甲醛 在 哌啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 苯 为溶剂， 反应 42.0h， 生成 2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran
  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

• SHARMA, ARUN P.;SAEED, ASHRAF;DURANI, SUSHEEL;KAPIL, RANDHIR S., J. MED. CHEM., 33,(1990) N2, C. 3216-3222
  作者：SHARMA, ARUN P.、SAEED, ASHRAF、DURANI, SUSHEEL、KAPIL, RANDHIR S.

  DOI：——

  日期：——
• 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：——