3-tetrahydropyran-2-yloxy-16-methoxycarbonyl-1,3,5(10)-estratrien-17-one | 1104732-26-4

• 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-tetrahydropyran-2-yloxy-16-methoxycarbonyl-1,3,5(10)-estratrien-17-one
• 英文别名: methyl (8R,9S,13S,14S)-13-methyl-3-(oxan-2-yloxy)-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16-carboxylate
• CAS: 1104732-26-4
• 化学式: C₂₅H₃₂O₅
• 分子量: 412.526
• InChiKey: IDMIGPLQFSBXDN-FQQVSXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-碘-丁酸乙酯 、 3-tetrahydropyran-2-yloxy-16-methoxycarbonyl-1,3,5(10)-estratrien-17-one 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以64%的产率得到3-tetrahydropyran-2-yloxy-16β-methoxycarbonyl-16α-(3-ethoxycarbonylpropyl)-1,3,5(10)-estratrien-17-one
  参考文献：
  名称：

  雌激素和维生素 D3 甾体杂化物的简单有效合成

  摘要：

  摘要描述了通过在类固醇核的 16 位修饰雌酮 (5) 来简单有效地合成雌激素和维生素 D3 的类固醇杂化物。

  DOI：

  10.1080/00397910802369620
• 作为产物：
  描述：

  3-tetrahydropyranyloxy-1,3,5(10)-estratrien-17-one 、 碳酸二甲酯 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到3-tetrahydropyran-2-yloxy-16-methoxycarbonyl-1,3,5(10)-estratrien-17-one
  参考文献：
  名称：

  雌激素和维生素 D3 甾体杂化物的简单有效合成

  摘要：

  摘要描述了通过在类固醇核的 16 位修饰雌酮 (5) 来简单有效地合成雌激素和维生素 D3 的类固醇杂化物。

  DOI：

  10.1080/00397910802369620

文献信息

• Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta
  作者：Caroline Descôteaux、Valérie Leblanc、Geoffroy Bélanger、Sophie Parent、Éric Asselin、Gervais Bérubé

  DOI：10.1016/j.steroids.2008.04.009

  日期：2008.10

  We have recently reported the synthesis of a platinum(II) complex, made of estradiol, the female sex hormone, and a cisplatin analog, an anticancer drug, linked together by an eleven carbon atoms chain. The novel estradiol-Pt(II) hybrid molecule was synthesized in nine chemical steps with 10% overall yield. This new compound has been tested in Vitro on estrogen-dependent (MCF-7) and -independent (MDA-MD-231) (ER(+) and ER(-)) cell lines. Interestingly, the biological activity was quite significant, more potent than that of cisplatin, the compound currently used in chemotherapy The estrogen receptor binding affinity (ERBA) of this compound was very similar to that of 17 beta-estradiol (E(2)) on both estrogen receptors (ERs), alpha and beta. In order to further study this type of molecule, we have decided to synthesize several analogs with the same estrogenic scaffold but with various chain lengths separating the estradiol from the toxic part of the molecule. This was planned in order to study the effect of the length of the linking chain on the biological activity of the hybrids. Four E(2)-Pt(II) hybrid molecules having 6-14 carbon atoms linking chain have been synthesized using a new synthetic methodology. They are synthesized in only eight chemical steps with 21% overall yield. The 17 beta-estradiol-linked-platinum(II) complexes have been tested for their receptor binding affinity as well as for their cytocidal activity on several breast cancer cell lines. The synthesis and biological results are reported herein. (c) 2008 Elsevier Inc. All rights reserved.
• Simple and Efficient Synthesis of Steroidal Hybrids of Estrogen and Vitamin D₃
  作者：Atul Gupta、Rachid Gueddah、Gervais Bérubé

  DOI：10.1080/00397910802369620

  日期：2008.12.16

  Abstract A simple and efficient synthesis of steroidal hybrids of estrogen and vitamin D3 through modification of estrone (5) at position 16 of the steroid nucleus is described.

  摘要描述了通过在类固醇核的 16 位修饰雌酮 (5) 来简单有效地合成雌激素和维生素 D3 的类固醇杂化物。