4-羟基雄烯二酮醋酸酯 | 61630-32-8

• 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
• 中文名称: 4-羟基雄烯二酮醋酸酯
• 英文名称: 3,17-dioxoandrost-4-en-4-yl acetate
• 英文别名: 4-acetoxy-4-androstene-3,17-dione；4-acetoxyandrost-4-ene-3,17-dione；4-acetoxyandrost-4-en-3,17-dione；4-acetoxyandrostenedione；[(8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
• CAS: 61630-32-8
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: LRXSFNGKRCOHRS-VMRCMBGLSA-N

物化性质

• 熔点：
  184-185 °C
• 沸点：
  501.2±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• LogP：
  2.325 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.761
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基雄烯二酮醋酸酯 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-Acetoxy-Δ^1,4-androstdiendion-(3,17)
  参考文献：
  名称：

  Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives

  摘要：

  The synthesis and biological evaluation of androstenedione derivatives as inhibitors of estrogen biosynthesis are described. The results show that 4-hydroxy analogues are among the most potent in vitro inhibitors of the series. Esterification of the 4-hydroxy steroids generally reduced activity. Further conjugation of the 3-keto 4-ene system to give 4-hydroxy-4,6-androstadiene-3,17-dione caused more rapid inactivation of aromatase in rat ovarian microsomes than 4-hydroxyandrostenedione. Some compounds exhibited differences in activity when tested for inhibition of human placental microsomes vs. rat ovarian microsomes. The 4-hydroxyandrostenedione derivatives and their nonbulky esters were generally more potent in vitro and in vivo inhibitors than other substituted steroids in the series. Several of the synthesized compounds markedly reduce (50-81%) estrogen levels in rats on proestrus and/or had antifertility action. To date, none of the compounds surpassed the in vivo inhibitory action of 4-hydroxy-4-androstene-3,17-dione or its 4-acetate derivative.

  DOI：

  10.1021/jm00383a017
• 作为产物：
  描述：

  4,5-epoxyandrostane-3,17-dione 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 4-羟基雄烯二酮醋酸酯
  参考文献：
  名称：

  Mann, John; Pietrzak, Barbara, Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2681 - 2685

  摘要：

  DOI：

文献信息

• Methods and compositions for the treatment of estrogen-dependent hyperproliferative uterine disorders
  申请人：Wang Changjin

  公开号：US20100087402A1

  公开（公告）日：2010-04-08

  The present invention relates to the treatment of estrogen-dependent hyperproliferative uterine disorders including endometriosis, uterine fibroids, endometrial hyperplasia, uterine cancer, and their related symptoms by intravaginally administering at least two active agents selected from an aromatase inhibitor, an antiinflammatory agent, and a uterine-selective estrogen receptor antagonist. This combination therapy reduces local estrogen production, blocks local estrogen action, and suppresses inflammation locally, resulting in starvation of the estrogen-dependent diseased tissues, relief of related symptoms, and retardation of disease progression. Intravaginal delivery maximizes local inhibition of estrogen production without significantly affecting systemic circulating estrogen levels. This results in enhanced clinical efficacy and reduced side effects.

  本发明涉及治疗依赖雌激素的子宫过度增生性疾病，包括子宫内膜异位症、子宫肌瘤、子宫内膜增生、子宫癌及其相关症状，通过阴道给药至少两种活性药物，所选药物包括芳香化酶抑制剂、抗炎药和子宫选择性雌激素受体拮抗剂。这种联合疗法降低了局部雌激素产生，阻断了局部雌激素作用，并在局部抑制了炎症，导致对依赖雌激素的疾病组织的饥饿，缓解相关症状，延缓疾病进展。阴道给药最大限度地抑制了局部雌激素产生，而不显著影响全身循环雌激素水平。这导致增强的临床疗效和减少的副作用。
• Topical treatment for mastalgia
  申请人：——

  公开号：US20040018991A1

  公开（公告）日：2004-01-29

  A composition for medicinal treatment by means of topical administration is described, which contains an aromatase inhibitor, in addition to conventional constituents of topical forms of administration. The active ingredient or the composition containing this active ingredient is especially suitable for the prophylaxis and for the treatment of mastalgia.

  本文描述了一种用于局部给药的医疗治疗组合物，其中包含一种芳香化酶抑制剂，除了传统的局部给药成分之外。这种活性成分或含有该活性成分的组合物特别适用于乳房疼痛的预防和治疗。
• composition and uses for influencing hair growth
  申请人：Schmidt Alfred

  公开号：US20110117218A1

  公开（公告）日：2011-05-19

  The invention describes a combination of at least one aromatase inhibitor selected from the group of chemical-synthetic aromatase inhibitors and aromatase inhibition exhibiting extracts of soya beans and rapeseed, respectively, and at least one plant extract that contains one or more active ingredient substance(s) extracted from the plant, which is(are) selected from the group of 5α reductase type I and/or type II inhibitors and androgen receptor blockers, said combination being contained for example in a composition and having special properties for influencing hair growth. Uses of this combination are also described.

  该发明描述了一种组合物，该组合物包括至少一种从化学合成芳香化酶抑制剂和大豆和油菜籽提取物中选择的芳香化酶抑制剂和至少一种植物提取物，该植物提取物含有从植物中提取的一个或多个活性成分，所述活性成分从5α还原酶I型和/或II型抑制剂和雄激素受体阻断剂中选择，该组合物例如包含在一种组合物中，并具有影响头发生长的特殊性质。还描述了该组合物的用途。
• Estrogen synthesis inhibitors
  申请人：THE ROCKEFELLER UNIVERSITY

  公开号：EP0161492A2

  公开（公告）日：1985-11-21

  Invention relates to 3-methylene substituted androst-4- ene-17-oxygenated compounds substituted with various substituents at the 10β-position which are useful as inhibitors of estrogen biosynthesis.

  本发明涉及在 10β 位上被各种取代基取代的 3-亚甲基取代雄-4-烯-17-氧化合物，这些化合物可用作雌激素生物合成的抑制剂。
• Pharmaceutical use
  申请人：Lucolas-M.D. Ltd.

  公开号：US10835540B2

  公开（公告）日：2020-11-17

  The invention relates to the use of a pharmaceutical medication comprising an aromatase inhibitor, preferably a steroidal aromatase inactivator and an antioxidant as effective ingredients for the treatment of sex hormone-dependent diseases. Furthermore, the invention relates to a composition comprising an aromatase inhibitor/—inactivator and α-lipoic acid and/or extract of green tea containing polyphenols. The combination of an aromatase inhibitor and—inactivator and α-lipoic acid and/or extract of green tea containing polyphenols is particularly suitable for the treatment of sex hormone-dependent diseases as well as for the treatment of benign tumors such as e.g. lipomatoses as occurring in Madelung's disease.

  本发明涉及一种由芳香化酶抑制剂（最好是类固醇芳香化酶灭活剂）和抗氧化剂组成的药物，作为治疗性激素依赖性疾病的有效成分。此外，本发明还涉及一种由芳香化酶抑制剂/灭活剂和α-硫辛酸和/或含有茶多酚的绿茶提取物组成的组合物。芳香化酶抑制剂和灭活剂与α-硫辛酸和/或含有茶多酚的绿茶提取物的组合特别适用于治疗性激素依赖性疾病以及良性肿瘤，例如马德龙氏病中出现的脂肪瘤。