3β,21-dihydroxy-5-pregnen-20-one | 1164-98-3

• 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: 3β,21-dihydroxy-5-pregnen-20-one
• 英文别名: Δ⁵-Pregnen-3,21-diol-20-on；3β,21-Dihydroxy-20-keto-pregn-5-en；3β,21-Dihydroxy-20-oxo-pregn-5-en；3β,21-Dihydroxy-pregn-5-en-20-on；3β-21-Dihydroxy-pregn-5-en-20-on；Pregn-5-en-3β,21-diol-20-on；2-hydroxy-1-[(3S,10R,13S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 1164-98-3；1499-61-2
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: MOIQRAOBRXUWGN-ANWDBCJUSA-N

物化性质

• 熔点：
  155-167°C
• 沸点：
  483.4±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

生物活性的21-羟基孕烯醇酮是皮质酮合成的重要中间体。其相关靶点为人内源性代谢物。

反应信息

• 作为产物：
  描述：

  pregnenolone 在 四氧化锇 、 正丁基锂 、 对甲苯磺酸 、 N,N-二甲基苯胺 、 N-甲基吗啉氧化物 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 35.0h， 生成 3β,21-dihydroxy-5-pregnen-20-one
  参考文献：
  名称：

  Synthesis of 17β-[4-(1,3-thiazolyl)]androstane 3β-hemisuccinate and glycoside

  摘要：

  保护的20(21)-烯-20-醇醚III被N-甲基吗啡啶N-氧化物单水合物和四氧化锇氧化，得到羟基酮IV，经过甲磺酸酯VI转化为溴取代物VIII。VIII溴酮与乙硫酰胺乙酯的Hantzsch反应得到噻唑XI，其半琥珀酸盐XIII和糖苷XV被制备出来。

  DOI：

  10.1135/cccc19841039

文献信息

• Antagonists of CB1 receptor
  申请人：INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE)

  公开号：US10040816B2

  公开（公告）日：2018-08-07

  The invention relates to an antagonist of CB1 receptor for use in the treatment of a pathologic condition or disorder selected from the group consisting of bladder and gastrointestinal disorders; inflammatory diseases; cardiovascular diseases; nephropathies; glaucoma; spasticity; cancer; osteoporosis; metabolic disorders; obesity; addiction, dependence, abuse and relapse related disorders; psychiatric and neurological disorders; neurodegenerative disorders; autoimmune hepatitis and encephalitis; pain; reproductive disorders and skin inflammatory and fibrotic diseases.

  本发明涉及一种 CB1 受体拮抗剂，用于治疗选自以下组别的病理状况或紊乱：膀胱和胃肠道疾病；炎症性疾病；心血管疾病；肾病；青光眼；痉挛；癌症；骨质疏松症；代谢紊乱；肥胖；成瘾、依赖、滥用和复发相关紊乱；精神和神经紊乱；神经退行性疾病；自身免疫性肝炎；骨质疏松症；代谢紊乱；肥胖；成瘾、依赖、滥用和复发相关疾病；精神和神经系统疾病；神经退行性疾病；自身免疫性肝炎和脑炎；疼痛；生殖系统疾病以及皮肤炎症和纤维化疾病。
• Antagonists of CB1 Receptor
  申请人：INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE)

  公开号：US20160145294A1

  公开（公告）日：2016-05-26

  The invention relates to an antagonist of CB1 receptor for use in the treatment of a pathologic condition or disorder selected from the group consisting of bladder and gastrointestinal disorders; inflammatory diseases; cardiovascular diseases; nephropathies; glaucoma; spasticity; cancer; osteoporosis; metabolic disorders; obesity; addiction, dependence, abuse and relapse related disorders; psychiatric and neurological disorders; neurodegenerative disorders; autoimmune hepatitis and encephalitis; pain; reproductive disorders and skin inflammatory and fibrotic diseases.
• ANTAGONISTS OF CB1 RECEPTOR
  申请人：Piazza Pier Vincenzo

  公开号：US20190071465A1

  公开（公告）日：2019-03-07

  The invention relates to an antagonist of CB1 receptor for use in the treatment of a pathologic condition or disorder selected from the group consisting of bladder and gastrointestinal disorders; inflammatory diseases; cardiovascular diseases; nephropathies; glaucoma; spasticity; cancer; osteoporosis; metabolic disorders; obesity; addiction, dependence, abuse and relapse related disorders; psychiatric and neurological disorders; neurodegenerative disorders; autoimmune hepatitis and encephalitis; pain; reproductive disorders and skin inflammatory and fibrotic diseases.
• Synthesis of 17β-[4-(1,3-thiazolyl)]androstane 3β-hemisuccinate and glycoside
  作者：Pavel Drašar、Vladimír Pouzar、Ivan Černý、Jorga Smolíková、Miroslav Havel

  DOI：10.1135/cccc19841039

  日期：——

  The protected 20(21)-en-20-ol ether III was oxidized with N-methylmorpholine N-oxide monohydrate and osmium tetroxide to give the hydroxy ketone IV which was converted into the bromo derivative VIII via the mesylate VI. Hantzsch reaction of the bromo ketone VIII with ethyl thioxamate afforded the thiazole XI whose hemisuccinate XIII and glycoside XV were prepared.

  保护的20(21)-烯-20-醇醚III被N-甲基吗啡啶N-氧化物单水合物和四氧化锇氧化，得到羟基酮IV，经过甲磺酸酯VI转化为溴取代物VIII。VIII溴酮与乙硫酰胺乙酯的Hantzsch反应得到噻唑XI，其半琥珀酸盐XIII和糖苷XV被制备出来。