4-(苯硫基)-4-雄甾烯-3,17,二酮 | 100513-95-9

• 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
• 中文名称: 4-(苯硫基)-4-雄甾烯-3,17,二酮
• 英文名称: 4-(phenylthio)-4-androstene-3,17-dione
• 英文别名: 4-phenylthio-4-androstene-3,17-dione；(8R,9S,10R,13S,14S)-10,13-dimethyl-4-phenylsulfanyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 100513-95-9
• 化学式: C₂₅H₃₀O₂S
• 分子量: 394.578
• InChiKey: CLKVUYDHWSHNGQ-BKCLIDBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(苯硫基)-4-雄甾烯-3,17,二酮 在 苯亚硒酸酐 作用下， 以 氯苯 为溶剂， 反应 0.5h， 以25%的产率得到4-phenylthio-androsta-1,4-diene-3,17-dione
  参考文献：
  名称：

  Aromatase inhibitors: Effect of ring A and ring B unsaturation on aromatase inhibition by 4-thiosubstituted derivatives of 4-androstene-3,17-dione

  摘要：

  The synthesis and biological evaluation of 4-thiosubstituted derivatives of 1,4-androstadienedione, 4,6-androstadienedione, and 1,4,6-androstatrienedione as inhibitors of aromatase are described. Inhibitory activity of synthesized compounds was assessed using a human placental microsomal preparation as the enzyme source and [1 beta-H-3]androstenedione as substrate. Under initial velocity assay conditions of low product formation, the inhibitors demonstrated potent inhibition of aromatase, with apparent K(i)s ranging from 9.8 to 137 nM and with K-m for androstenedione being 38 nM. However, unlike other 1,4-androstadienediones and 1,4,6-androstatrienediones in which time-dependent inactivation was observed, the 4-thiosubstituted analogs were found to be competitive inhibitors and did not produce any time-dependent inactivation of aromatase.

  DOI：

  10.1016/0039-128x(95)00020-q
• 作为产物：
  描述：

  苯硫酚 、 (4β,5)-epoxy-5β-androstan-3,17-dione 在 sodium 作用下， 反应 8.0h， 以83%的产率得到4-(苯硫基)-4-雄甾烯-3,17,二酮
  参考文献：
  名称：

  合成和评估4-（取代的硫代）-4-雄烯-3,17-二酮衍生物作为潜在的芳香化酶抑制剂。

  摘要：

  描述了作为雌激素合成酶（芳香酶）抑制剂的4-（取代硫代）-4-雄烯-3,17-二酮衍生物的合成和评价。通过将各种硫醇试剂添加到4 beta，5β-环氧雄烷二酮中来制备所有化合物。以人胎盘微粒体制剂为酶源，以[1β-3H] -4-雄烯酮-3,17-二酮为底物，测定合成化合物的抑制活性。在初始速度条件下进一步评估了表现出高抑制活性的合成化合物，以确定表观Ki值。几种化合物是有效的竞争性抑制剂，其表观Ki值范围为36至73 nM，雄烯二酮的表观Km为53 nM。

  DOI：

  10.1021/jm00154a025

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。
• Composition and uses for influencing hair growth
  申请人：S.W. Patentverwertungs Limited

  公开号：US11052059B2

  公开（公告）日：2021-07-06

  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.

  本发明描述了至少一种芳香化酶抑制剂（分别选自化学合成芳香化酶抑制剂和具有芳香化酶抑制作用的大豆和油菜籽萃取物）与至少一种植物萃取物的组合，该植物萃取物含有一种或多种从植物中提取的活性成分物质，这些活性成分物质选自 5α 还原酶 I 型和/或 II 型抑制剂以及雄激素受体阻断剂。此外，还介绍了这种组合物的用途。
• Aromatase marking
  申请人：——

  公开号：US20040241087A1

  公开（公告）日：2004-12-02

  Compounds are described which exhibit an inhibitory action towards the enzyme aromatase and which comprise at least one detectable group. Such compounds are excellently suitable for medical diagnosis and/or for therapy, particularly for tumor diseases and above all for breast cancer.

  所述化合物对芳香化酶具有抑制作用，并包含至少一个可检测基团。这些化合物非常适合医学诊断和/或治疗，特别是肿瘤疾病，尤其是乳腺癌。