4-Methyl-androst-4-en-3,17-dion | 5696-39-9

• 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
• 英文名称: 4-Methyl-androst-4-en-3,17-dion
• 英文别名: 4-Methyl-androsten-(4)-dion-(3,17)；4-Methyl-4-androsten-3,17-dione；(8R,9S,10R,13S,14S)-4,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 5696-39-9
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: ISMVMNHPEDSOTR-TXDMSJPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Methyl-androst-4-en-3,17-dion 在 吡啶 、 甲醇 、 甲基溴化镁 、 sodium methylate 、 对甲苯磺酸 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 34.8h， 生成 (17α)-4-methyl-1'-(methylsulfonyl)-1'H-pregn-4-en-20-yno<3,2-c>pyrazol-17-ol
  参考文献：
  名称：

  Antiandrogenic steroidal sulfonylpyrazoles

  摘要：

  The steroidal sulfonylpyrazole 1 bound to the rat ventral prostate androgen receptor in vitro; it inhibited testosterone propionate induced increases in ventral prostate weight in vivo in the castrated, immature male rat with an ED50 of 15 mg/kg po. Compound 1 lacked androgenic activity in vivo in contrast to the parent steroidal pyrazole 5, which was both androgenic and antiandrogenic. The 2'- and 5'-methylsulfonyl isomers 6 and 6a did not bind to the androgen receptor. Introduction of an alkylsulfonyl at the N-1'-position has served, therefore, to isolate the intrinsic antiandrogenic properties of the steroidal heterocycle free of apparent hormone agonist properties. Structure-activity relationship studies revealed that a methylsulfonyl group at N-1' together with a C-17 alpha-substituent were the optimal combination for in vitro androgen receptor binding, in vivo antiandrogenic potency, and a lack of androgenic activity.

  DOI：

  10.1021/jm00170a008
• 作为产物：
  描述：

  睾酮 在 potassium tert-butylate 、 dipyridine chromium trioxide 作用下， 以 叔丁醇 为溶剂， 生成 4-Methyl-androst-4-en-3,17-dion
  参考文献：
  名称：

  4-Substituted Steroids¹

  摘要：

  DOI：

  10.1021/ja01496a044

文献信息

• 6-substituted androsta-1,4-diene-3,17-diones
  申请人：Farmitalia Carlo Erba S.r.l.

  公开号：US04808616A1

  公开（公告）日：1989-02-28

  The invention relates to 6-alkylidenandrosta-1,4-diene-3,17-dione derivatives, having the following general formula ##STR1## wherein each of R and R.sub.2, independently, is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.1 is hydrogen, halogen or C.sub.1 -C.sub.6 alkyl, which are useful in therapy, in particular in the treatment of hormone-dependent cancers.

  这项发明涉及6-烷基亚雄甾-1,4-二烯-3,17-二酮衍生物，具有以下一般式##STR1##其中R和R.sub.2中的每一个独立地是氢或C.sub.1-C.sub.6烷基，R.sub.1是氢、卤素或C.sub.1-C.sub.6烷基，这些衍生物在治疗中特别是在治疗激素依赖性癌症方面是有用的。
• Substituted androsta-1,4-diene-3,17-diones
  申请人：Farmitalia Carlo Erba S.p.A.

  公开号：US04904650A1

  公开（公告）日：1990-02-27

  The invention relates to 6-alkylidenadrosta-1,4-diene-3,17-dione derivatives, having the following general formula ##STR1## wherein each of R and R.sub.2, independently, is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.1 is hydrogen, halogen or C.sub.1 -C.sub.6 alkyl, which are useful in therapy, in particular in the treatment of hormone-dependent cancers.

  本发明涉及6-烷基亚甲基-睾酮酮-1,4-二烯-3,17-二酮衍生物，其具有以下通式：##STR1## 其中R和R.sub.2各自独立地为氢或C.sub.1-C.sub.6烷基，R.sub.1为氢，卤素或C.sub.1-C.sub.6烷基，该衍生物在治疗方面有用，特别是在治疗激素依赖性癌症方面。
• 20-Fluoro-17(20)-vinyl steroids
  申请人：——

  公开号：US20020019548A1

  公开（公告）日：2002-02-14

  The invention related to 20&xgr;-fluoropregna-4,17(20)-dien-3-on-21-oic acid ethyl ester, 20&xgr;-fluoro-3&bgr;-hydroxypregna-4,17(20)-dien-21-oic acid ethyl ester, 20&xgr;-fluoro-21-hydroxypregna-4,17(20)-dien-3-one, 20&xgr;-fluoropregna-4,17(20)-dien-3&bgr;,21-diol and related compounds and to compositions incorporating these compounds, as well as the inhibition of C 17,20 lyase, 5&agr;-reductase and C 17 -hydroxylase, and to the use of these compounds in the treatment of androgen and estrogen mediated or dependent disorders, including benign prostatic hyperplasia, prostate cancer, breast cancer and DHT-mediated disorders such as acne and hirsutism. Treatment of disorders related to the over synthesis of cortisol, for example, Cushing's Syndrome are also included. The treatment of androgen-dependent disorders also includes a combination therapy with known androgen-receptor antagonists, such as flutamide. The compounds of the invention have the following general formulae: 1

  本发明涉及20&xgr;-氟孕-4,17（20）-二烯-3-酮-21-羧酸乙酯，20&xgr;-氟-3&bgr;-羟基孕-4,17（20）-二烯-21-羧酸乙酯，20&xgr;-氟-21-羟基孕-4,17（20）-二烯-3-酮，20&xgr;-氟孕-4,17（20）-二烯-3&bgr;，21-二醇及其相关化合物，以及包含这些化合物的组合物，以及抑制C17,20裂解酶、5&agr;-还原酶和C17-羟化酶，并将这些化合物用于治疗雄激素和雌激素介导或依赖性疾病，包括良性前列腺增生症、前列腺癌、乳腺癌和DHT介导的疾病，如痤疮和多毛症。本发明还包括治疗与皮质醇过度合成有关的疾病，例如库欣综合征。雄激素依赖性疾病的治疗还包括与已知雄激素受体拮抗剂（如氟他胺）的联合治疗。本发明的化合物具有以下一般式：1
• Antiandrogens
  申请人：Endorecherche

  公开号：US06015806A1

  公开（公告）日：2000-01-18

  Androgen nucleus derivatives having specified substituents at the 17.alpha. position are disclosed for use as antiandrogens for the treatment of androgen-dependent diseases. In some preferred embodiments, the compound ##STR1## is formulated together with pharmaceutically acceptable diluent or carrier for topical use in the treatment of androgen-dependent diseases associated with the skin.

  本发明揭示了在17α位点具有指定取代基的雄激素核衍生物，用于作为抗雄激素治疗雄激素依赖性疾病。在一些优选实施例中，化合物##STR1##与药学上可接受的稀释剂或载体一起制剂，用于治疗与皮肤相关的雄激素依赖性疾病。
• Julia,S.; Moutonnier,C., Bulletin de la Societe Chimique de France, 1964, p. 321 - 330
  作者：Julia,S.、Moutonnier,C.

  DOI：——

  日期：——