3-acetoxy-11β-hydroxy-estra-1,3,5(10)-trien-17-one | 95342-26-0

• 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: 3-acetoxy-11β-hydroxy-estra-1,3,5(10)-trien-17-one
• 英文别名: 3-Acetoxy-11β-hydroxy-oestra-1,3,5(10)-trien-17-on；[(8S,9S,11S,13S,14S)-11-hydroxy-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 95342-26-0
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: ODYCPVNRWDWDOS-CAVMOMJPSA-N

物化性质

• 熔点：
  185-187 °C
• 沸点：
  497.3±45.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxy-11β-hydroxy-estra-1,3,5(10)-trien-17-one 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 7.0h， 生成 3-benxyloxy-11β-hydroxyestra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Nonpolar and Short Side Chain Groups at C-11β of Estradiol Result in Antiestrogens

  摘要：

  We have previously found that esters of 11beta-estradiol carboxylates are transformed from an estrogen into an antiestrogen when the 11beta-side chain is increased in length from four to five non-hydrogen atoms (n greater than or equal to 5). To understand the structural requirements for this transformation and obtain metabolically stable analogues that are not susceptible to esterase cleavage, we have synthesized other compounds having an 11beta-side chain composed of other functional groups: ketones, amides, ethers, and thiono esters. With the exception of amides, which bind poorly to the estrogen receptor (ER), all of these compounds exhibit antiestrogenic action when the side chain length is n greater than or equal to 5. Ethers (n greater than or equal to 5), studied in more detail, inhibit the action of estradiol with either ERalpha or ERbeta. In rat uteri they are estrogen antagonists/weak agonists and decrease the concentration of cholesterol in blood (an hepatic estrogenic action). Thus, these short chain and nonpolar 11beta-analogues of estradiol have tissue specific antiestrogenic/estrogenic actions, characteristics of selective estrogen receptor modulators.

  DOI：

  10.1021/jm049352x
• 作为产物：
  描述：

  乙酸雌酮 在 三乙基硅烷 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 3-acetoxy-11β-hydroxy-estra-1,3,5(10)-trien-17-one
  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

文献信息

• Stereochemistry of Steroids containing Aromatic A-Ring. II. Reaction of 9α, 11α-Epoxyestrone.
  作者：Hiroko Hasegawa、Shigeo Nozoe、Kyosuke Tsuda

  DOI：10.1248/cpb.11.1037

  日期：——

  The reduction of 3-hydroxy-9α, 11α-epoxyestra-1, 3, 5 (10)-trien-17-one (III) with lithium aluminum hydride gave estra-1, 3, 5 (10)-triene-3, 11α, 17β-triol. The reaction of III with hydrogen chloride in methanol yielded 3-hydroxy-9β-estra-1, 3, 5 (10)-triene-11, 17-dione (IXa). On the other hand, the reaction in chloroform afforded 9ξ-chloro-3, 11α-dihydroxyestra-1, 3, 5 (10)-trien-17-one (VIIIa). With alkali 3-hydroxyestra-1, 3, 5 (10)-triene-11, 17-dione (Va) is converted into 9β-isomer (IXa).

  3-羟基-9α,11α-环氧雌甾-1,3,5(10)-三烯-17-酮（III）与氢化铝锂反应生成雌甾-1,3,5(10)-三烯-3,11α,17β-三醇。III与甲醇中的氯化氢反应生成3-羟基-9β-雌甾-1,3,5(10)-三烯-11,17-二酮（IXa）。另一方面，在氯仿中的反应生成9ξ-氯-3,11α-二羟基雌甾-1,3,5(10)-三烯-17-酮（VIIIa）。在碱的作用下，3-羟基雌甾-1,3,5(10)-三烯-11,17-二酮（Va）转化为9β-异构体（IXa）。
• [EN] 9 alpha , 11 beta -SUBSTITUTED AND 11 beta -SUBSTITUTED ESTRANES
  申请人：SRI INTERNATIONAL

  公开号：WO1987000175A1

  公开（公告）日：1987-01-15

  (EN) 9$g(a), 11$g(b) and 11$g(b)-susbstituted estranes which exhibit elevated estrogenic and postcoital contraceptive activities. A process for their manufacture and their use in pharmaceuticals is also disclosed.(FR) Des oestrones 9$g(a), 11$g(b) et 11$g(b) substituées présentent des effets oestrogènes et contraceptifs prononcés après des rapports sexuels. L'invention concerne également leur procédé de production et d'utilisation dans des substances pharmaceutiques.

  经甾体9g(a)、11g(b)及11g(b)-取代雌二烯酮，经ER具有高度雌作用和雄性交后的避孕性能。该发明还包含这些化合物的制备工艺及其用于药品中的应用。
• Structure-activity relationships of estrogens: Effects of esterification of the 11β-hydroxyl group
  作者：Albert Segaloff、R.Bruce Gabbard

  DOI：10.1016/0039-128x(84)90063-1

  日期：1984.1

  Fourteen esters (formate, acetate, propionate, butyrate, hexanoate, heptanoate, and benzoate) located at C-11 of 11 beta-hydroxyesterone and 11 beta-hydroxyestradiol-17 beta were synthesized and evaluated for uterotropic and gonadotropin release inhibition in rats, as well as their ability to displace (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor. The most potent uterotropic agent was 11 beta-formoxyestrone which was 1,625 or 2,500 times as active as 11 beta-hydroxyesterone in the uterotropic or gonadotropin release inhibition assay, respectively. 11 beta-Formoxyestrone was 7.5 times as uterotropic as estradiol-17 beta and equal to estradiol-17 beta in inhibiting gonadotropin release. However, the most potent inhibitor of gonadotropin release was 11 beta-acetoxy-estradiol-17 beta which had 133% of the activity of estradiol-17 beta, although it had only 38% of the activity of estradiol-17 beta in the uterotropic assay. Esters larger than the acetoxy group showed sharply decreased activities in either assay. Despite the high estrogenic potency of the 11-formates or 11-acetates, they were rather weak (6% to 35% as active as estradiol-17 beta) in displacing (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor.
• Golubovskaya; Rzheznikov, Russian Journal of Organic Chemistry, 1997, vol. 33, # 4, p. 559 - 560
  作者：Golubovskaya、Rzheznikov

  DOI：——

  日期：——
• 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：——