17α-(E-2-iodovinyl)-Δ^1,3,5-estratrien-3,17β-diol-3 methyl ester | 78479-31-9

• 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: 17α-(E-2-iodovinyl)-Δ^1,3,5-estratrien-3,17β-diol-3 methyl ester
• 英文别名: 17α-(E-2-iodovinyl)-Δ^1,3,5-estratrien-3,17β-diol-3-methyl ether；(17α,20E)-21-iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-(methyl ether)；(17α,20E)-21-iodo-3-methoxy-19-norpregna-1,3,5(10),20-tetraen-17-ol；(E)-17α-(iodovinyl)mestranol；17α-(2-iodovinyl)-3-methoxy-1,3,5(10)-estratrien-17β-ol；(8R,9S,13S,14S,17R)-17-[(E)-2-iodoethenyl]-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS: 78479-31-9
• 化学式: C₂₁H₂₇IO₂
• 分子量: 438.349
• InChiKey: CNXYYKZZDGUKQL-FLCMJHBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-(E-2-iodovinyl)-Δ^1,3,5-estratrien-3,17β-diol-3 methyl ester 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以81%的产率得到3-甲氧基-19-去甲-17-alpha-孕甾-1,3,5(10)-三烯-17-beta-醇
  参考文献：
  名称：

  Synthesis and evaluation of (17.alpha.,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diol and (17.alpha.,20E)-21-[125I]iodo-11.beta.-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol [17.alpha.-iodovinyl)estradiol derivatives] as high specific activity potential radiopharmaceuticals

  摘要：

  Two 17 alpha-[125I]iodovinyl estradiol derivatives 4b,d possessing high specific activity have been prepared and tested as potential radiopharmaceuticals. The use of the 3-acetyl derivatives 2c,e and the replacement of iodine monochloride with sodium iodide and Chloramine-T in THF/phosphate buffer (pH 7.0) permitted us to synthesize no-carrier-added (17 alpha,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-d iol (4b) and (17 alpha,20E)-21-[125I]iodo-11 beta-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol (4d) with 50% radiochemical yield and high purity. Although the specific activity represents only half of the theoretical value in some cases, this modified approach is a substantial improvement over the previously published method. Our preliminary distribution studies indicate that although both 4b and 4d localize in the tissues known to have a large concentration of estrogen receptors, 4d accumulates in higher amounts in target tissues and provides a high target to nontarget ratio.

  DOI：

  10.1021/jm00376a010
• 作为产物：
  描述：

  美雌醇 在 水 、 sodium acetate 、 一氯化碘 、 儿萘酚硼烷 作用下， 生成 17α-(E-2-iodovinyl)-Δ^1,3,5-estratrien-3,17β-diol-3 methyl ester
  参考文献：
  名称：

  Kabalka, George W.; Gooch, E. Eugene; Hsu, Henry C., Synthetic Communications, 1981, vol. 11, # 3, p. 247 - 252

  摘要：

  DOI：

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, 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.
• Kabalka, George W.; Sastry, Kunda A. R.; Somayaji, Vishwanatha, Heterocycles, 1982, vol. 18, p. 157 - 161
  作者：Kabalka, George W.、Sastry, Kunda A. R.、Somayaji, Vishwanatha

  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：——