18-羟基-4-雄甾烯-3,17-二酮 | 7121-60-0

• 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
• 中文名称: 18-羟基-4-雄甾烯-3,17-二酮
• 英文名称: 18-Hydroxyandrost-4-ene-3,17-dione
• 英文别名: 18-hydroxy androstenedione；18-Hydroxy-4-androstene-3,17-dione；(8R,9S,10R,13S,14S)-13-(hydroxymethyl)-10-methyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 7121-60-0
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: ZZHNYTLKRMBVAI-NLPXPOPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  18-羟基-4-雄甾烯-3,17-二酮 在 四丁基氯化铵 、 三乙胺 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 18-Chloroandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Synthesis of 18-substituted androst-4-en-3-one derivatives as potential inhibitors of aldosterone biosynthesis

  摘要：

  Androst-4-en-3-one derivatives substituted at the 18-methyl group bearing a 17-keto or 17-spirolactone function have been synthesized and tested in vitro as inhibitors of aldosterone biosynthesis.

  DOI：

  10.1016/s0040-4020(01)89733-7
• 作为产物：
  描述：

  17β-Hydroxy-18-acetoxyandrost-4-ene-3-one 在 盐酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 18-羟基-4-雄甾烯-3,17-二酮
  参考文献：
  名称：

  Synthesis of 18-substituted androst-4-en-3-one derivatives as potential inhibitors of aldosterone biosynthesis

  摘要：

  Androst-4-en-3-one derivatives substituted at the 18-methyl group bearing a 17-keto or 17-spirolactone function have been synthesized and tested in vitro as inhibitors of aldosterone biosynthesis.

  DOI：

  10.1016/s0040-4020(01)89733-7

文献信息

• Method and product for increasing fertility in sheep using milk protein
  申请人：The Director General of the Ministry of Agriculture and Fisheries

  公开号：US04749567A1

  公开（公告）日：1988-06-07

  A product and method for increasing fertility in sheep. By "increasing felity" is meant increasing the potential of a flock of sheep to multiply by increasing ovulation in ewes. The product is an immunogenic conjugate of 4-androstene-3, 17-dione and a soluble milk protein (SMP): 6-hydroxyandrost-4-ene-3, 17-dione 6-hemisuccinyl: SMP. The method comprises immunizing the ewes in a flock of sheep against 4-androstene-3, 17-dione by administering 6-hydroxyandrost-4-ene-3, 17-dione 6-hemisuccinyl SMP at the rate of 3 to 5 mg per ewe. In previously untreated ewes, two administrations are required at between 8 to 9 and 4 to 5 weeks before the planned commencement of mating. Subsequent administrations are annually and are recommended at 5 weeks before the commencement of mating.

  一种增加绵羊生育能力的产品和方法。所谓“增加生育能力”是指通过增加母羊排卵来增加绵羊群体的繁殖潜力。该产品是4-雄烯-3，17-二酮和可溶性乳蛋白（SMP）的免疫原性结合物：6-羟基雄烯-4-烯-3，17-二酮6-半琥珀酰基：SMP。该方法包括对绵羊群体中的母羊进行免疫，以抗体6-羟基雄烯-4-烯-3，17-二酮6-半琥珀酰基SMP每只母羊3至5毫克的比例给药。对于以前未接受治疗的母羊，需要在计划交配前8至9周和4至5周之间进行两次给药。随后的给药每年进行一次，建议在交配开始前5周进行。
• Aspergillus ochraceus 11 alpha hydroxylase and oxidoreductase
  申请人：Bolten L. Suzanne

  公开号：US20050003473A1

  公开（公告）日：2005-01-06

  The present invention relates to a novel cytochrome P450-like enzyme ( Aspergillus ochraceus 11 alpha hydroxylase) and an oxidoreductase ( Aspergillus ochraceus oxidoreductase) isolated from cDNA library generated from the mRNA of Aspergillus ochraceus spores. When the cDNA encoding the 11 alpha hydroxylase was co-expressed in Spodoptera frugiperda (Sf-9) insect cells with the cDNA encoding human oxidoreductase as an electron donor, it successfully catalyzed the conversion of the steroid substrate 4-androstene-3,17-dione (AD) to 11 alpha-hydroxy-AD as determined by HPLC analysis. The invention also relates to nucleic acid molecules associated with or derived from these cDNAs including complements, homologues and fragments thereof, and methods of using these nucleic acid molecules, to generate, for example, polypeptides and fragments thereof. The invention also relates to the generation of antibodies that recognizes the A. ochraceus 11 alpha hydroxylase and oxidoreductase and methods of using these antibodies to detect the presence of these native and recombinant polypeptides within unmodified and transformed host cells, respectively. The invention also provides methods of expressing the Aspergillus 11 alpha hydroxylase gene separately, or in combination with human or Aspergillus oxidoreductase, in heterologous host cells, to facilitate the bioconversion of steroid substrates to their 11 alpha hydroxy-counterparts.

  本发明涉及一种新型细胞色素P450样酶（曲霉11α-羟化酶）和氧化还原酶（曲霉氧化还原酶），这些酶是从曲霉孢子的mRNA产生的cDNA文库中分离出来的。当编码11α-羟化酶的cDNA与编码人类氧化还原酶的cDNA在斯氏福斯虫细胞中共同表达时，成功地催化了类固醇底物4-雄烯-3,17-二酮（AD）转化为11α-羟基-AD，这是通过HPLC分析确定的。本发明还涉及与这些cDNA相关或衍生的核酸分子，包括其互补物、同源物和片段，以及使用这些核酸分子生成多肽和其片段的方法。本发明还涉及生成识别曲霉11α-羟化酶和氧化还原酶的抗体，以及使用这些抗体检测这些天然和重组多肽在未修改和转化宿主细胞中的存在的方法。本发明还提供在异源宿主细胞中分别或与人类或曲霉氧化还原酶结合表达曲霉11α-羟化酶基因的方法，以促进类固醇底物向其11α-羟基对应物的生物转化。
• Synthese d'une nouvelle lactone en serie steroide: Une hydrolyse de nitrile en milieu neutre
  作者：Philippe Schambel、Antoinette Viger、Andrée Marquet

  DOI：10.1016/s0040-4039(00)95566-7

  日期：——

  Treatment of 18-hydroxy androstenedione with acetone cyanohydrin under neutral conditions yielded intermediate which was hydrolyzed in situ by intramolecular attack of the vicinal 18-hydroxyl group, leading to the lactone .

  在中性条件下用丙酮氰醇处理18-羟基雄烯二酮产生中间体，该中间体通过邻位18-羟基的分子内攻击原位水解，从而产生内酯。
• Microbiological preparation of 9-alpha-hydroxy-17-keto steroids
  申请人：ROUSSEL-UCLAF

  公开号：EP0322081A1

  公开（公告）日：1989-06-28

  9α-hydroxy-17-keto steroids are prepared by fermenting steroids having a C-17 side chain of 5-10 carbon atoms inclusive, with the novel Mycobacterium species CBS 482.86. Starting from various substrates containing a 5-10 C carbon chain an C-17, 9α-hydroxyandrost-4-ene-3,17-dione, 7α,9α,12α-trihydroxyandrost-4-ene-3,17-dione or 9α-­hydroxyandrost-4,11-diene-3,17-dione are obtained in high yield. The resulting compounds are useful intermediates in the synthesis of therapeutically important steroids, particularly corticosteroids.

  新型分枝杆菌 CBS 482.86 通过发酵具有 5-10 个碳原子的 C-17 侧链的类固醇，制备出 9α-羟基-17-酮类固醇。 从含有 5-10 个碳原子的 C-17 侧链的各种底物开始，可以高产率地获得 9α-羟基雄甾-4-烯-3,17-二酮、7α,9α,12α-三羟基雄甾-4-烯-3,17-二酮或 9α-羟基雄甾-4,11-二烯-3,17-二酮。 所得化合物是合成具有重要治疗作用的类固醇，特别是皮质类固醇的有用中间体。
• NEUROACTIVE 19-ALKOXY-17-SUBSTITUTED STEROIDS, USEFUL IN METHODS OF TREATMENT
  申请人：Washington University

  公开号：EP4086270A1

  公开（公告）日：2022-11-09

  The present disclosure is generally directed to neuroactive 19-alkoxy-17-substituted steroids as referenced herein, and pharmaceutically acceptable salts thereof, for use as, for example, an anesthetic, and/or in the treatment of disorders relating to GABA function and activity. The present disclosure is further directed to pharmaceutical compositions comprising such compounds.

  本公开总体上涉及本文提及的神经活性 19-烷氧基-17-取代类固醇及其药学上可接受的盐类，用于例如麻醉剂和/或治疗与 GABA 功能和活性有关的疾病。本公开进一步涉及包含此类化合物的药物组合物。