17α-E-(3-pyridyl)-vinyl estradiol

• 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: 17α-E-(3-pyridyl)-vinyl estradiol
• 英文别名: 17α-E-(3-pyridyl)vinyl estradiol；(8R,9S,13S,14S,17R)-13-methyl-17-[(E)-2-pyridin-3-ylethenyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• 化学式: C₂₅H₂₉NO₂
• 分子量: 375.511
• InChiKey: YQQGHJUDNAYWRM-YTHSSNJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-碘吡啶 、 (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 在 二(三叔丁基膦)钯 、 cesium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 以22%的产率得到17α-E-(3-pyridyl)-vinyl estradiol
  参考文献：
  名称：

  Synthesis and evaluation of 17α-E-20-(heteroaryl)norpregn-1,3,5(10),20 tetraene-3,17β-diols [17α-(heteroaryl)vinyl estradiols] as ligands for the estrogen receptor-α ligand binding domain (ERα-LBD)

  摘要：

  A series of 17 alpha-(heteroaryl)vinyi estradiols was prepared to evaluate the influence of heteroatom on the affinity and efficacy of estrogenic ligands for the estrogen receptor-alpha ligand binding domain (ER alpha-LBD). The products demonstrated reduced binding affinity compared to the parent 17 alpha-E-phenylvinyl estradiol, but the binding was relatively independent of the heteroatom. The greatest influence of the heteroatom was evident in the efficacy of the compounds as the thienyl derivatives 2f,g were more potent than either the pyridyl 2b-d or pyrimidinyl 2e analogs. The results suggest that a subtle interplay of interactions between the ligands and the receptor influences the biological response. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.003

文献信息

• Targeting the estrogen receptor with metal-carbonyl derivatives of estradiol
  作者：Robert N. Hanson、Rein Kirss、Emmett McCaskill、Edward Hua、Pakamas Tongcharoensirikul、Sandra L. Olmsted、David Labaree、Richard B. Hochberg

  DOI：10.1016/j.bmcl.2011.12.111

  日期：2012.2

  As part of our program to develop new probes for the estrogen receptor binding domain, we prepared and evaluated a novel 17 alpha-(rhenium tricarbonyl bipyridyl) vinyl estradiol complex. Preparation of the final compound was achieved using the Stille coupling between the preformed brominated rhenium tricarbonyl bipyridine complex and the tributylstannyl vinyl estradiol. Competitive receptor binding assays and stimulatory assays demonstrated that the final complex retained affinity and efficacy comparable to the corresponding pyridyl vinyl estradiol analog, but lower than that of the phenyl vinyl estradiol analog. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of 17α-E-20-(heteroaryl)norpregn-1,3,5(10),20 tetraene-3,17β-diols [17α-(heteroaryl)vinyl estradiols] as ligands for the estrogen receptor-α ligand binding domain (ERα-LBD)
  作者：Sandra L. Olmsted、Pakamas Tongcharoensirikul、Emmett McCaskill、Karla Gandiaga、David Labaree、Richard B. Hochberg、Robert N. Hanson

  DOI：10.1016/j.bmcl.2011.12.003

  日期：2012.1

  A series of 17 alpha-(heteroaryl)vinyi estradiols was prepared to evaluate the influence of heteroatom on the affinity and efficacy of estrogenic ligands for the estrogen receptor-alpha ligand binding domain (ER alpha-LBD). The products demonstrated reduced binding affinity compared to the parent 17 alpha-E-phenylvinyl estradiol, but the binding was relatively independent of the heteroatom. The greatest influence of the heteroatom was evident in the efficacy of the compounds as the thienyl derivatives 2f,g were more potent than either the pyridyl 2b-d or pyrimidinyl 2e analogs. The results suggest that a subtle interplay of interactions between the ligands and the receptor influences the biological response. (C) 2011 Elsevier Ltd. All rights reserved.