7α-<11-(4-iodophenoxy)undecyl>estra-1,3,5(10)-triene-3,17β-diol | 123266-49-9

• 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: 7α-<11-(4-iodophenoxy)undecyl>estra-1,3,5(10)-triene-3,17β-diol
• 英文别名: (7R,8R,9S,13S,14S,17S)-7-[11-(4-iodophenoxy)undecyl]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 123266-49-9
• 化学式: C₃₅H₄₉IO₃
• 分子量: 644.677
• InChiKey: PUATYBXLOTXELQ-WTELBQNKSA-N

物化性质

• 熔点：
  66-67 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  697.1±55.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7α-(11-hydroxyundecyl)estra-1,3,5(10)-triene-3,17β-diol 在 四溴化碳 、 碳酸氢钠 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 7α-<11-(4-iodophenoxy)undecyl>estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  Synthesis and structure-affinity of a series of 7.alpha.-undecylestradiol derivatives: a potential vector for therapy and imaging of estrogen-receptor-positive cancers

  摘要：

  A series of 7 alpha-undecylestradiol derivatives, featuring various substituents at the end of the undecyl spacer chain, were synthesized and evaluated for their interaction with the estrogen receptor and nonreceptor sites. Their relative binding affinities (RBA) for calf uterine estrogen receptors were measured by competitive binding assays and varied between 0.5 and 8.4% of that of unlabeled 17 beta-estradiol. Enhanced lipophilicity and steric hindrance of the substituent on the end of the spacer chain resulted in decreased binding affinity for the estrogen receptor, while interactions with nonreceptor sites increased. RBA values were not affected by prolonged incubation times, suggesting a stable ligand-receptor complex. The potential to use the 7 alpha-undecylestradiol as a vector for site-selective delivery of diagnostic and therapeutic moieties to estrogen-receptor-positive human cancers is discussed.

  DOI：

  10.1021/jm00163a066

文献信息

• DASILVA, JEAN N.;VAN, LIER JOHAN E., J. MED. CHEM., 33,(1990) N, C. 430-434
  作者：DASILVA, JEAN N.、VAN, LIER JOHAN E.

  DOI：——

  日期：——
• Synthesis and structure-affinity of a series of 7.alpha.-undecylestradiol derivatives: a potential vector for therapy and imaging of estrogen-receptor-positive cancers
  作者：Jean N. DaSilva、Johan E. Van Lier

  DOI：10.1021/jm00163a066

  日期：1990.1

  A series of 7 alpha-undecylestradiol derivatives, featuring various substituents at the end of the undecyl spacer chain, were synthesized and evaluated for their interaction with the estrogen receptor and nonreceptor sites. Their relative binding affinities (RBA) for calf uterine estrogen receptors were measured by competitive binding assays and varied between 0.5 and 8.4% of that of unlabeled 17 beta-estradiol. Enhanced lipophilicity and steric hindrance of the substituent on the end of the spacer chain resulted in decreased binding affinity for the estrogen receptor, while interactions with nonreceptor sites increased. RBA values were not affected by prolonged incubation times, suggesting a stable ligand-receptor complex. The potential to use the 7 alpha-undecylestradiol as a vector for site-selective delivery of diagnostic and therapeutic moieties to estrogen-receptor-positive human cancers is discussed.