(Z)-(Iodovinyl)estradiol | 104011-19-0

• 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: (Z)-(Iodovinyl)estradiol
• 英文别名: (Z)-17α-(iodovinyl)estradiol；(Z)-17α-(2-iodovinyl)-1,3,5(10)-estratriene-3,17β-diol；17α-(Z-2-iodovinyl)-1,3,5(10)-estratriene-3,17β-diol；(8R,9S,13S,14S,17R)-17-[(Z)-2-iodoethenyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 104011-19-0
• 化学式: C₂₀H₂₅IO₂
• 分子量: 424.322
• InChiKey: DQQMDOLPKAVVIE-CKMNJZPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 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 sodium hydroxide 、 碘 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 0.08h， 生成 (Z)-(Iodovinyl)estradiol
  参考文献：
  名称：

  雌激素配体的结构活性关系：（17 alpha，20E）-和（17 alpha，20Z）-21-halo-19-norpregna-1,3,5（10），20-tetraene-3， 17种β-二醇。

  摘要：

  作为我们探索雌激素受体结合分子需求的程序的一部分，我们进行了17α，E和17 alpha，Z卤代戊二烯雌二醇的合成和评估。通过使用现有合成策略的改进方案，从相应的17α，E或17α，Z [（三-正丁基锡烷基）乙烯基]雌二醇3-立体定向制备目标化合物，产率为92-98％。醋酸盐。使用大鼠子宫制剂评估了新型雌二醇衍生物对雌激素受体的相对结合亲和力（RBA）。结果表明，E和Z异构体之间以及所用卤素之间存在显着差异。Z异构体具有较高的RBA值，较大的卤素（I，Br）比较小的Cl取代基更有效。这些结果修改了以前对甾体配体的雌激素受体结合的解释。结果，我们设计的（放射性）卤代配体将考虑到Z与E立体化学的关系。

  DOI：

  10.1021/jm00113a012

文献信息

• Estrogenic 17.alpha.-halogen-vinylestranes
  申请人：Schering Aktiengesellschaft

  公开号：US04725426A1

  公开（公告）日：1988-02-16

  17.alpha.-bromo-.alpha. and 17.alpha.-iodo-vinyl-estrane derivatives of general formula I ##STR1## wherein X is a bromine or iodine atom in Z or E position, R.sup.1 is hydrogen, hydroxy or acyloxy with up to 3 C atoms, R.sup.2 is hydrogen, alkyl with up to 3 C atoms and alkanoyl and aroyl with up to 7 C atoms, R.sup.3 is hydrogen or methyl, R.sup.4 is a hydrogen atom in the .alpha. or .beta. position, R.sup.5 is hydrogen, methyl or methoxy and R.sup.6 is hydrogen or methyl, are pharmacologically effective with a profile of action like ethinylestradiol and in the form of their radioactively labeled compounds are also valuable diagnostic media. The Z-isomers can be prepared by a new process by reaction of the corresponding 17.alpha.-ethinyl steroids with trialkyl (or phenyl) tin hydride with addition of a free radical former.

  17.alpha.-溴-.alpha.和17.alpha.-碘-乙烯基-雌甾烷衍生物的一般化学式I如下：其中X是Z或E位置的溴或碘原子，R.sup.1是氢、羟基或酰氧基，碳原子数最多为3，R.sup.2是氢、碳原子数最多为3的烷基以及碳原子数最多为7的烷酰基和芳酰基，R.sup.3是氢或甲基，R.sup.4是.alpha.或.beta.位置的氢原子，R.sup.5是氢、甲基或甲氧基，R.sup.6是氢或甲基，具有药理学作用，其作用特点类似于乙炔雌二醇，并且以其放射性标记化合物的形式也是有价值的诊断介质。Z-异构体可以通过一种新的方法制备，即将相应的17.alpha.-乙炔类固醇与三烷基（或苯基）锡氢化合物反应，并加入自由基前体。
• Synthesis of 17α-(Iodovinyl)estradiol and Analogous Derivatives by Iododestannylation of Insoluble Polymer-Supported Organotin Precursors
  作者：Gilles Dumartin、Jamil Kharboutli、Bernard Delmond、Yves Frangin、Michel Pereyre

  DOI：10.1002/(sici)1099-0690(199904)1999:4<781::aid-ejoc781>3.0.co;2-f

  日期：1999.4

  Iodoestrogen derivatives were prepared by iododestannylation of insoluble polymer-supported organotin precursors.

  碘代雌激素衍生物是通过不溶性聚合物负载的有机锡前体的碘去烯基化反应制得的。
• Synthesis and evaluation of radioiodinated estrogens for diagnosis and therapy of male urogenital tumours
  作者：Feodor Braun、Marcel Jaschinski、Philipp Täger、Verena Marmann、Melanie von Brandenstein、Barbara Köditz、Thomas Fischer、Sergio Muñoz-Vázquez、Beate Zimmermanns、Markus Dietlein、Ferdinand Sudbrock、Phillip Krapf、Dietmar Fischer、Axel Heidenreich、Alexander Drzezga、Stefan Kirsch、Markus Pietsch、Klaus Schomäcker

  DOI：10.1039/d3ob00114h

  日期：——

  We identified a new estrogen receptor (ER)-targeting ligand with picomolar affinity serving as vehicle for radioiodines. This ligand is a potential radiotheranostics for ER⁺ male tumours.

  我们发现了一种新的雌激素受体（ER）靶向配体，它具有皮摩尔亲和力，可作为放射性碘的载体。这种配体是治疗ER+男性肿瘤的潜在放射治疗药物。
• Synthesis, receptor binding, and tissue distribution of (17.alpha.,20E)- and (17.alpha.,20Z)-21-[125I]Iodo-19-norpregna-1,3,5-(10),20-tetraene-3,17-diol
  作者：H. Ali、J. Rousseau、M. A. Ghaffari、J. E. Van Lier

  DOI：10.1021/jm00118a013

  日期：1988.10

  The isomeric (17 alpha,20E)- and (17 alpha,20Z)-(iodovinyl)estradiol derivatives 3 and 6, and their no-carrier-added (nca) [125I]iodovinyl analogues, were tested for their relative target tissue retention and binding affinity for the estrogen receptor. The (iodovinyl)estradiols 3 and 6 were prepared via destannylation of the (17 alpha,20E)- and (17 alpha,20Z)-tributylstannyl precursors 2 and 4 with retention of configuration. Selective formation of the E or Z isomers 2 and 4 during the reaction of 17 alpha-ethynylestradiol 1a with tri-n-butyltin hydride was controlled by the presence or absence of the catalyst, the polarity of the solvent, and the reaction temperature. The nca [125I]iodovinyl analogues [125I]-3a and [125I]-6a were obtained in good radiochemical yield and high purity by treatment of 2a and 4a with [125I]NaI in the presence of H2O2 and chloroamine-T, respectively. Of the two isomeric iodovinyl derivatives 3 and 6, the 20Z isomer 6a exhibited the highest receptor binding affinity and the [125I]-6a gave the highest in vivo receptor-mediated target tissue uptake.
• ALI, H.;ROUSSEAU, J.;CHAFFARI, M. A.;VAN, LIER J. E., J. MED. CHEM., 31,(1988) N 10, C. 1946-1950
  作者：ALI, H.、ROUSSEAU, J.、CHAFFARI, M. A.、VAN, LIER J. E.

  DOI：——

  日期：——