7α-methylestrone acetate | 36014-09-2

• 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: 7α-methylestrone acetate
• 英文别名: [(7R,8R,9S,13S,14S)-7,13-dimethyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 36014-09-2
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: FRHUCMWUOPTVRN-REMQMKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7α-methylestrone acetate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 6.0h， 以10.5 g的产率得到3,9α,11β-trihydroxy-7α-methylestra-1,3,5(10)-trien-17-one 3-acetate 11-nitrate ester
  参考文献：
  名称：

  11.beta.-Nitrate estrane analogs: potent estrogens

  摘要：

  Various estrane derivatives 1 reacted with cerium ammonium nitrate (CAN) selectively and efficiently to provide 9 alpha,11 beta-defunctionalized derivatives 2, which were subsequently deoxygenated at C-9 with triethylsilane/boron trifluoride etherate to the desired target 11 beta-nitratoestranes 3a, 3b, and 5. When examined for estrogenic and postcoital antifertility activity, 11 beta-nitrates 2c, 2d, and 3b most notably displayed more potent oral activity than did ethynylestradiol.

  DOI：

  10.1021/jm00130a014
• 作为产物：
  描述：

  乙酸异丙烯酯 、 阿美雌酮 在 硫酸 作用下， 反应 2.0h， 以54%的产率得到7α-methylestra-1,3,5(10),16-tetraene-3,17-diol diacetate
  参考文献：
  名称：

  7.alpha.-Methyl- and 11.beta.-ethoxy-substitution of iodine-125-labeled [125I]16.alpha.-iodoestradiol: effect on estrogen receptor-mediated target tissue uptake

  摘要：

  The 7alpha-methyl and 11beta-ethoxy derivatives of 16alpha-[I-125]iodoestradiol were prepared via halogen exchange with I-125 of the corresponding 16beta-bromoestradiol precursors. The 16alpha-bromo derivatives were obtained via halogenation of the analogous 17-enol acetate, epimerization to the 16beta-isomer, and hydride reduction. Stereochemical assignments were based on high resolution H-1 NMR. To evaluate the effect of the nature and stereochemistry of the 16-halo substituent on the relative binding affinity for the estrogen receptor, the analogous 16-chloro derivatives were also prepared. The highest binding affinities were observed with the 7alpha-methyl-16alpha-haloestradiols, particularly the bromo and chloro derivatives while the 16alpha-iodo derivatives gave somewhat lower values. Both the 11beta-ethoxy and 7alpha-methyl-16alpha-[I-125]iodoestradiols localize in the uteri of immature female rats via a receptor-mediated process. Rapid blood clearance of the I-125-labeled 7alpha-methyl derivative results in lower I-125 uptake by the uterus as well as nontarget organs as compared to the 11beta-substituted estradiol analogs. However, uterus to blood and nontarget ratios are more favorable for the 7alpha-methyl-16alpha-[I-125]iodoestradiol as compared to the analogous 11beta-ethoxy derivatives suggesting that this compound substituted with I-125 may be useful for the in vivo imaging of estrogen receptor-rich breast tumors by single photon emission computerized tomography.

  DOI：

  10.1021/jm00054a011

文献信息

• [EN] ORALLY ACTIVE DERIVATIVES OF 1,3,5(10)-ESTRATRIENE<br/>[FR] DERIVES DE 1,3,5(10)-ESTRATRIENE ACTIFS PAR VOIE ORALE
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1995007925A1

  公开（公告）日：1995-03-23

  (EN) 17$g(b)-nitrate and 11$g(b),17$g(b)-dinitrate esters of estradiol which exibit elevated estrogenic and postcoital contraceptive activities are disclosed. A process for their manufacture and their use in pharmaceuticals is also disclosed.(FR) L'invention concerne décrit des dinitrate-17$g(b)-nitrate et 11$g(b)-,17$g(b)-ester d'estradiol, qui présentent une activité oestrogénique et contraceptive postcoïtale élevée. Un procédé pour leur fabrication et leur utilisation dans des produits pharmaceutiques est également décrit.

  本发明涉及17β-降噪酸根和11β,17β-二降硝酸酯的雌二醇 esters，这些化合物具有显著的雌激素活性和避孕作用后受精作用。此外，还描述了这些化合物的制备过程及其药用方法。
• PETERS, RICHARD H.;CROWE, DAVID F.;AVERY, MITCHELL A.;CHONG, WESLEY K. M.+, J. MED. CHEM., 32,(1989) N0, C. 2306-2310
  作者：PETERS, RICHARD H.、CROWE, DAVID F.、AVERY, MITCHELL A.、CHONG, WESLEY K. M.+

  DOI：——

  日期：——
• CROWE, DAVID E.;TANABE, MASATO;PETERS, RICHARD
  作者：CROWE, DAVID E.、TANABE, MASATO、PETERS, RICHARD

  DOI：——

  日期：——
• 11-BETA-NITRATE-SUBSTITUTED ESTRANES
  申请人：SRI INTERNATIONAL

  公开号：EP0227813B1

  公开（公告）日：1991-10-02
• ORALLY ACTIVE DERIVATIVES OF 1,3,5(10)-ESTRATRIENE
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by the SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0719276B1

  公开（公告）日：1997-11-26