1-(2-hydroxyphenyl)-2-<4-<(tetrahydropyran-2-yl)oxy>phenyl>-3-(4-hydroxyphenyl)prop-2-en-1-one | 130064-23-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxyphenyl)-2-<4-<(tetrahydropyran-2-yl)oxy>phenyl>-3-(4-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 1-(2-hydroxyphenyl)-2-<4-(tetrahydropyran-2-yloxy)phenyl>-3-(4-hydroxyphenyl)prop-2-en-1-one；(E)-1-(2-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-[4-(oxan-2-yloxy)phenyl]prop-2-en-1-one
• CAS: 130064-23-2
• 化学式: C₂₆H₂₄O₅
• 分子量: 416.474
• InChiKey: LEIXLCBXYUMVCM-HAVVHWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-2-<4-<(tetrahydropyran-2-yl)oxy>phenyl>-3-(4-hydroxyphenyl)prop-2-en-1-one 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 45.0h， 生成 1-[2-(4-{3-[4-(Tetrahydro-pyran-2-yloxy)-phenyl]-2H-chromen-2-yl}-phenoxy)-ethyl]-piperidine
  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
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 哌啶 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 34.0h， 生成 1-(2-hydroxyphenyl)-2-<4-<(tetrahydropyran-2-yl)oxy>phenyl>-3-(4-hydroxyphenyl)prop-2-en-1-one
  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

文献信息

• Synthesis and post-coital contraceptive activity of a new series of substituted 2,3-diaryl-2H-1-benzopyrans
  作者：K Hajela、RS Kapil

  DOI：10.1016/s0223-5234(97)87540-x

  日期：1997.1

  A series of substituted 2,3-diaryl-2H-1-benzopyrans have been synthesized and screened for their post-coital contraceptive activity in rats. Most of the compounds showed 100% inhibition in a single day schedule at a dose level of 1.0 mg/kg. Compound 32 was found to be the most active with a minimum effective dose (MED) of 0.2 mg/kg in single day testing. Further, it also showed high antiestrogenic activity and is devoid of any agonistic activity.
• SHARMA, ARUN P.;SAEED, ASHRAF;DURANI, SUSHEEL;KAPIL, RANDHIR S., J. MED. CHEM., 33,(1990) N2, C. 3222-3229
  作者：SHARMA, ARUN P.、SAEED, ASHRAF、DURANI, SUSHEEL、KAPIL, RANDHIR S.

  DOI：——

  日期：——