3-acetoxy-(17α,20Z)-21-[(4-fluoro)phenyl]-19-norpregna-1,3,5(10),20-tetraene-17β-ol | 859233-86-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-acetoxy-(17α,20Z)-21-[(4-fluoro)phenyl]-19-norpregna-1,3,5(10),20-tetraene-17β-ol
• 英文别名: [(8R,9S,13S,14S,17R)-17-[(Z)-2-(4-fluorophenyl)ethenyl]-17-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 859233-86-6
• 化学式: C₂₈H₃₁FO₃
• 分子量: 434.551
• InChiKey: WZWAMZJZXGNGCE-NJHOLIOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxy-(17α,20Z)-21-[(4-fluoro)phenyl]-19-norpregna-1,3,5(10),20-tetraene-17β-ol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以31%的产率得到(17α,20Z)-21-[(4-fluoro)phenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol
  参考文献：
  名称：

  Synthesis and Evaluation of (17α,20Z)-21-(4-Substituted-phenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols as Ligands for the Estrogen Receptor-α Hormone Binding Domain:  Comparison with 20E-Isomers

  摘要：

  As part of our ongoing program to develop probes for the hormone binding domain of the estrogen receptor-alpha (ER alpha), we prepared and evaluated a series of 17 alpha,Z-(4-substituted-phenyl)-vinyl estradiol derivatives. The results indicated that the relative binding affinities (RBAs) at 25 degrees C for the new compounds were significant (RBA = 9-57) although less than that of estradiol (RBA = 100) or of the parent unsubstituted phenylvinyl estradiol (RBA = 66). All of the Z-compounds were full agonists in the uterotrophic assay, indicating that the ligands formed estrogen-like complexes with the estrogen receptor-alpha hormone binding domain (ER alpha-HBD). Comparison of corresponding Z- and E-4-substituted phenylvinyl ligands complexed with the ER alpha-HBD indicated small but significant differences in binding modes that may account for the differing trends seen in the structure-activity relationships for the two series.

  DOI：

  10.1021/jm040157s
• 作为产物：
  描述：

  3-acetoxy-(17α,20Z)-21-(tri-n-butylstannyl)-19-norpregna-1,3,5(10),20-tetraene-17β-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-碘代丁二酰亚胺 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 3-acetoxy-(17α,20Z)-21-[(4-fluoro)phenyl]-19-norpregna-1,3,5(10),20-tetraene-17β-ol
  参考文献：
  名称：

  Synthesis and Evaluation of (17α,20Z)-21-(4-Substituted-phenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols as Ligands for the Estrogen Receptor-α Hormone Binding Domain:  Comparison with 20E-Isomers

  摘要：

  As part of our ongoing program to develop probes for the hormone binding domain of the estrogen receptor-alpha (ER alpha), we prepared and evaluated a series of 17 alpha,Z-(4-substituted-phenyl)-vinyl estradiol derivatives. The results indicated that the relative binding affinities (RBAs) at 25 degrees C for the new compounds were significant (RBA = 9-57) although less than that of estradiol (RBA = 100) or of the parent unsubstituted phenylvinyl estradiol (RBA = 66). All of the Z-compounds were full agonists in the uterotrophic assay, indicating that the ligands formed estrogen-like complexes with the estrogen receptor-alpha hormone binding domain (ER alpha-HBD). Comparison of corresponding Z- and E-4-substituted phenylvinyl ligands complexed with the ER alpha-HBD indicated small but significant differences in binding modes that may account for the differing trends seen in the structure-activity relationships for the two series.

  DOI：

  10.1021/jm040157s