2-((14-iodotetradecyl)oxy)tetrahydro-2H-pyran | 1123595-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-((14-iodotetradecyl)oxy)tetrahydro-2H-pyran
• CAS: 1123595-31-2
• 化学式: C₁₉H₃₇IO₂
• 分子量: 424.406
• InChiKey: QZXQSHZMQFYQLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  22.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((14-iodotetradecyl)oxy)tetrahydro-2H-pyran 、 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 24.0h， 生成
  参考文献：
  名称：

  Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2008.04.009
• 作为产物：
  描述：

  1-bromo-14-(tetrahydropyranyloxy)tetradecane 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以98%的产率得到2-((14-iodotetradecyl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Improved synthesis of unique estradiol-linked platinum(II) complexes showing potent cytocidal activity and affinity for the estrogen receptor alpha and beta

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2008.04.009