16α-bromo-3-acetoxy-7α-cyanoestra-1,3,5(10)-triene-17-one | 669707-41-9

• 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: 16α-bromo-3-acetoxy-7α-cyanoestra-1,3,5(10)-triene-17-one
• CAS: 669707-41-9
• 化学式: C₂₁H₂₂BrNO₃
• 分子量: 416.315
• InChiKey: KBWFBCRVWZCTIN-TYWALRRJSA-N

反应信息

• 作为反应物：
  描述：

  16α-bromo-3-acetoxy-7α-cyanoestra-1,3,5(10)-triene-17-one 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以80%的产率得到16α-bromo-3-hydroxy-7α-cyanoestra-1,3,5(10)-triene-17-one
  参考文献：
  名称：

  Synthesis and biological properties of 7α-cyano derivatives of the (17α,20E/Z)-[125I]iodovinyl- and 16α-[125I]iodo-estradiols

  摘要：

  The synthesis, receptor binding affinity, estrogenic potency and tissue distribution of the 7alpha-cyano derivatives of the (17alpha,20E/Z)-[I-125]iodovinyl-(CIVE) and 16alpha-[I-125]iodo-estradiols (CIE) are reported. The iodovinyl derivatives were prepared via the (17alpha,20E/Z)-tri-n-butylstannyl intermediates, derived from the addition of tri-n-butyl tin hydride to the 17alpha-ethynyl group of the 7alpha-cyano-17alpha-ethynylestradiol, using triethylborane as a catalyst. The no-carrier-added [I-125]-CIVE isomers were prepared via the same stereospecific reaction. [I-125]-CIE was prepared from 7alpha-cyano-16beta-bromoestradiol via halogen exchange with (NaI)-I-125. Addition of the 7alpha-cyano group to 16alpha-iodoestradiol did not affect estrogen receptor binding affinity (RBA of CIE is 415). However the estrogenic potential of CIE, as measured by the capacity to stimulate the expression of the pS2 gene, was reduced to 1% as compared to that of estradiol. Addition of a 7alpha-cyano group to the (17alpha,20E/Z)-IVE isomers reduced the RBA to 21 and 36, respectively, while the estrogenic potential was reduced to 2-3% of that of estradiol. Uterus uptake in immature rats of the I-125-labeled CIVE 20E-isomer and the 16alpha-iodo CIE peaked at 0.5 h post injection while the (17alpha,20Z)-CIVE isomer showed a maximum only past 5 h post injection. Uptake of all three I-125-labeled 7alpha-cyanoestrogens was suppressed by the co-injection of non-radioactive estradiol confirming the role of estrogen receptors in the localization process. Uterus retention pattern differ substantially from those of the analogues 7alpha-methylestrogens, which were previously shown to give high maximum I-125-uptake values at 2 h post injection. Overall our data indicate that addition of a 7alpha-cyano group to I-123-labeled estrogens does not improve their potential to serve as SPECT agents for the imaging of estrogen receptor densities in breast cancer. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2003.09.005
• 作为产物：
  描述：

  7α-cyanoestra-1,3,5(10)-16-tetraene-3,17-diol diacetate 在 溴 作用下， 以 乙醚 、 acetate buffer 、 溶剂黄146 为溶剂， 反应 0.17h， 以75%的产率得到16α-bromo-3-acetoxy-7α-cyanoestra-1,3,5(10)-triene-17-one
  参考文献：
  名称：

  Synthesis and biological properties of 7α-cyano derivatives of the (17α,20E/Z)-[125I]iodovinyl- and 16α-[125I]iodo-estradiols

  摘要：

  The synthesis, receptor binding affinity, estrogenic potency and tissue distribution of the 7alpha-cyano derivatives of the (17alpha,20E/Z)-[I-125]iodovinyl-(CIVE) and 16alpha-[I-125]iodo-estradiols (CIE) are reported. The iodovinyl derivatives were prepared via the (17alpha,20E/Z)-tri-n-butylstannyl intermediates, derived from the addition of tri-n-butyl tin hydride to the 17alpha-ethynyl group of the 7alpha-cyano-17alpha-ethynylestradiol, using triethylborane as a catalyst. The no-carrier-added [I-125]-CIVE isomers were prepared via the same stereospecific reaction. [I-125]-CIE was prepared from 7alpha-cyano-16beta-bromoestradiol via halogen exchange with (NaI)-I-125. Addition of the 7alpha-cyano group to 16alpha-iodoestradiol did not affect estrogen receptor binding affinity (RBA of CIE is 415). However the estrogenic potential of CIE, as measured by the capacity to stimulate the expression of the pS2 gene, was reduced to 1% as compared to that of estradiol. Addition of a 7alpha-cyano group to the (17alpha,20E/Z)-IVE isomers reduced the RBA to 21 and 36, respectively, while the estrogenic potential was reduced to 2-3% of that of estradiol. Uterus uptake in immature rats of the I-125-labeled CIVE 20E-isomer and the 16alpha-iodo CIE peaked at 0.5 h post injection while the (17alpha,20Z)-CIVE isomer showed a maximum only past 5 h post injection. Uptake of all three I-125-labeled 7alpha-cyanoestrogens was suppressed by the co-injection of non-radioactive estradiol confirming the role of estrogen receptors in the localization process. Uterus retention pattern differ substantially from those of the analogues 7alpha-methylestrogens, which were previously shown to give high maximum I-125-uptake values at 2 h post injection. Overall our data indicate that addition of a 7alpha-cyano group to I-123-labeled estrogens does not improve their potential to serve as SPECT agents for the imaging of estrogen receptor densities in breast cancer. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2003.09.005