17α-(1-propenyl)estra-1,3,5(10)-triene-3,17β-diol | 101915-79-1

• 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-(1-propenyl)estra-1,3,5(10)-triene-3,17β-diol
• 英文别名: 17-α-propynylestradiol；17-α-(1-propynyl)estradiol；(8R,9S,13S,14S,17S)-13-methyl-17-prop-1-ynyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 101915-79-1
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: GJUHUIXJLZINMA-MJCUULBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-(1-propenyl)estra-1,3,5(10)-triene-3,17β-diol 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 三正丁基氢锡 、 乙酰氯 作用下， 生成 17α-(cis-1-propenyl)estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  11.beta.-Substituted Estradiol Derivatives, Potential High-Affinity Carbon-11-Labeled Probes for the Estrogen Receptor: A Structure-Affinity Relationship Study

  摘要：

  In view of their possible development as carbon-11-labeled receptor-based radiotracers for imaging estrogen-responsive breast tumors, we have synthesized a series of estradiols (1), estriols (2), 11 beta-ethylestradiols (3), 11 beta-ethylestriols (4), 11 beta-methoxyestradiols (5), and 11 beta-methoxyestriols (6), differing in the type of substituent R present at the 17 alpha-position (a, -H; b, -CH3; c, -C=CH; d, -C=CCH3; e, -Ph; f, -CH=CHMe cis), and measured their binding affinity for the estrogen receptor relative to estradiol(RBA): As expected, all the derivatives having an 11 beta-ethyl substituent have good binding properties (3a-d, 4a-d, RBA (25 degrees C): 109-3000%), and among them there are several promising candidates for carbon-11 labeling. Moxestrol (RBA (25 degrees C) = 185%) and its corresponding estriol derivative (4c, RBA (25 degrees C) = 20%) were the analogs having the highest affinity in the 11 beta-methoxyestradiol (5a-f) and 11 beta-methoxyestriol (6a-e) series, respectively; other analogs (R = Me, C=CMe, Ph, or cis-CH=CHMe) had uniformly lower RBA values.

  DOI：

  10.1021/jm00003a005
• 作为产物：
  描述：

  在 甲醇 、 乙酰氯 作用下， 以 乙酸乙酯 为溶剂， 生成 17α-(1-propenyl)estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  11.beta.-Substituted Estradiol Derivatives, Potential High-Affinity Carbon-11-Labeled Probes for the Estrogen Receptor: A Structure-Affinity Relationship Study

  摘要：

  In view of their possible development as carbon-11-labeled receptor-based radiotracers for imaging estrogen-responsive breast tumors, we have synthesized a series of estradiols (1), estriols (2), 11 beta-ethylestradiols (3), 11 beta-ethylestriols (4), 11 beta-methoxyestradiols (5), and 11 beta-methoxyestriols (6), differing in the type of substituent R present at the 17 alpha-position (a, -H; b, -CH3; c, -C=CH; d, -C=CCH3; e, -Ph; f, -CH=CHMe cis), and measured their binding affinity for the estrogen receptor relative to estradiol(RBA): As expected, all the derivatives having an 11 beta-ethyl substituent have good binding properties (3a-d, 4a-d, RBA (25 degrees C): 109-3000%), and among them there are several promising candidates for carbon-11 labeling. Moxestrol (RBA (25 degrees C) = 185%) and its corresponding estriol derivative (4c, RBA (25 degrees C) = 20%) were the analogs having the highest affinity in the 11 beta-methoxyestradiol (5a-f) and 11 beta-methoxyestriol (6a-e) series, respectively; other analogs (R = Me, C=CMe, Ph, or cis-CH=CHMe) had uniformly lower RBA values.

  DOI：

  10.1021/jm00003a005

文献信息

• Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived 11CH3-labeled PET tracers with a 1-propynyl groupElectronic supplementary information (ESI) available: general experimental remarks and synthetic methods and characterization of tributylalkynylstannanes and the corresponding methylacetylenes. See http://www.rsc.org/suppdata/ob/b3/b311532a/
  作者：Takamitsu Hosoya、Masahiro Wakao、Yurie Kondo、Hisashi Doi、Masaaki Suzuki

  DOI：10.1039/b311532a

  日期：——

  The Pd(0)-mediated rapid coupling (trapping) reaction of methyl iodide with an excess amount of alkynyltributylstannane has been developed with the aim to incorporate a short-lived (11)C-labeled methyl group into biologically active organic compounds with a 1-propynyl structural unit.

  已开发出Pd（0）介导的甲基碘与过量的炔基三丁基锡烷的快速偶联（捕获）反应，旨在将短寿命的（11）C标记的甲基掺入具有1的生物活性有机化合物中-丙炔基结构单元。
• 11.beta.-Substituted Estradiol Derivatives, Potential High-Affinity Carbon-11-Labeled Probes for the Estrogen Receptor: A Structure-Affinity Relationship Study
  作者：Elio Napolitano、Rita Fiaschi、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1021/jm00003a005

  日期：1995.2

  In view of their possible development as carbon-11-labeled receptor-based radiotracers for imaging estrogen-responsive breast tumors, we have synthesized a series of estradiols (1), estriols (2), 11 beta-ethylestradiols (3), 11 beta-ethylestriols (4), 11 beta-methoxyestradiols (5), and 11 beta-methoxyestriols (6), differing in the type of substituent R present at the 17 alpha-position (a, -H; b, -CH3; c, -C=CH; d, -C=CCH3; e, -Ph; f, -CH=CHMe cis), and measured their binding affinity for the estrogen receptor relative to estradiol(RBA): As expected, all the derivatives having an 11 beta-ethyl substituent have good binding properties (3a-d, 4a-d, RBA (25 degrees C): 109-3000%), and among them there are several promising candidates for carbon-11 labeling. Moxestrol (RBA (25 degrees C) = 185%) and its corresponding estriol derivative (4c, RBA (25 degrees C) = 20%) were the analogs having the highest affinity in the 11 beta-methoxyestradiol (5a-f) and 11 beta-methoxyestriol (6a-e) series, respectively; other analogs (R = Me, C=CMe, Ph, or cis-CH=CHMe) had uniformly lower RBA values.