[125I]-(E)-(Iodovinyl)estradiol | 91085-44-8

• 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: [125I]-(E)-(Iodovinyl)estradiol
• 英文别名: (E)-(Iodovinyl)estradiol；(E)-17α-(iodovinyl)estradiol；17α-[(E)-2-iodovinyl]-estra-1,3,5(10)-triene-3,17β-diol；(8R,9S,13S,14S,17R)-17-[(E)-2-iodoethenyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 91085-44-8
• 化学式: C₂₀H₂₅IO₂
• 分子量: 424.322
• InChiKey: DQQMDOLPKAVVIE-XTJNFZKPSA-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：

  (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 在 碘 作用下， 以 氯仿 为溶剂， 以82.5%的产率得到[125I]-(E)-(Iodovinyl)estradiol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00118a013

文献信息

• 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。
• Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17.alpha.,20E)- and (17.alpha.,20Z)-21-halo-19-norpregna-1,3,5(10),20-tetraene-3,17.beta.-diols
  作者：Elio Napolitano、Rita Fiaschi、Robert N. Hanson

  DOI：10.1021/jm00113a012

  日期：1991.9

  affinity (RBA) for the estrogen receptor with use of a rat uterine preparation. The results demonstrated a marked difference between the E and Z isomers and among the halogen employed. The Z isomers possessed significantly higher RBA values and the larger halogens (I, Br) were more effective than the smaller Cl substituent. These results modify the previous interpretations of estrogen-receptor binding for

  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。
• 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。
• PILLAI, K. M. R.;MCLAUGHLIN, W. H.;LAMBRECHT, R. M.;BLOOMER, W. D., J. LABELL. COMPOUNDS AND RADIOPHARM., 24,(1987) N 9, 1117-1122
  作者：PILLAI, K. M. R.、MCLAUGHLIN, W. H.、LAMBRECHT, R. M.、BLOOMER, W. D.

  DOI：——

  日期：——
• 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：——