3β-hydroxy-pregn-5-en-20-one | 145-13-1

• 物质功能分类: 天然产物 - 甾体化合物
• 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-hydroxy-pregn-5-en-20-one
• 英文别名: 3-Hydroxy-20-oxopregn-5-en；Pregnenolon；Pregmnolon；pregnenolone；1-[(10R,13S)-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: 145-13-1；566-63-2；19037-28-6；38372-24-6
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: ORNBQBCIOKFOEO-OYZZJKLHSA-N

物化性质

• 熔点：
  188-190 °C
• 比旋光度：
  28.5 º (c=1, EtOH)
• 沸点：
  395.89°C (rough estimate)
• 密度：
  1.0382 (rough estimate)
• 闪点：
  9℃
• 溶解度：
  乙醇：可溶10mg/mL，澄清，无色至淡黄色
• LogP：
  4.4 at 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2937290090
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  TU5560700

制备方法与用途

生物活性

Pregnenolone 是一种内源性类固醇激素，能够抑制 M1 受体和 M3 受体介导的电流，其 IC50 分别为 11.4 µM 和 6.0 µM。

靶点

• 目标：孕激素受体

体外研究

Pregnenolone 在剂量相关地诱导 MAP2 促进微管蛋白组装的速率和程度方面表现出作用，而 progesterone 却没有活性并抵消了 Pregnenolone 的刺激作用。Pregnenolone 引起的微管组装增加，形成一个完全正常的结构。此外，它还保持微管丰富，并在外包过程中促进细胞运动。在小鼠海马细胞株（HT-22）中，Pregnenolone 导致孕激素受体核定位显著减少。Pregnenolone 对谷氨酸和 β 淀粉样蛋白具有神经病理学的神经保护作用。

体内研究

在完整雄性 SCID 小鼠和去势动物中，Pregnenolone 维持其体内增殖活性并刺激 LNCaP 肿瘤异种移植物的生长。Pregnenolone 通过激活 LNCaP 雄激素受体（AR），而不是野生型 AR，来转录。在这些动物模型中，Pregrenolone 还导致星形胶质细胞在伤口附近显著减少，并使大鼠活性星形细胞中溴脱氧尿苷掺入的水平显著降低。此外，Pregnenolone 促进了下游神经甾体 allopregnanolone 的增加，后者具有神经保护作用，能增加神经发生、减少细胞凋亡和炎症、调节下丘脑-垂体-肾上腺轴，并显着地提高 GABA（A）受体的反应性。Pregnenolone 还提高了 Pregnenolone 硫酸盐的水平，后者是积极调节 NMDA 受体的神经甾体。

化学性质

Pregnenolone 是一种白色结晶粉末，熔点为 193℃，不溶于水。其溶解度（g/100ml）如下：四氯化碳 0.5、石油醚 0.1、乙酸乙酯 1.1、丙酮 0.6、氯仿 17.0、乙醇 1.9、苯 0.9、异丙醇 1.5、丙二醇 0.1、二氧六环 3.1、苄醇 8.1。

用途

Pregnenolone 主要用于生化研究，并作为激素类药物黄体酮的中间体。此外，它还可用于甾体类药物中间体和甾体类药物的合成，以及用作医药黄体酮的中间体。

生产方法

将乙酸妊娠双烯醇酮、乙醇与雷氏镍一起加热至 50℃左右使其溶解，然后抽真空通入氢气，反复3次后，在搅拌下通氢，在 34-36℃反应 3.5h。静置，通氮气排出氢气，滤出催化剂。将滤液浓缩回收大部分乙醇，析出结晶。将结晶投入水解锅内减压蒸尽乙醇，冷却后加入甲醇加热回流使其溶解，加入 50% 碳酸钾水溶液，回流 1.5h，减压浓缩回收甲醇，出料后冷却至 5℃以下，滤取结晶，用温水洗至中性烘干。再用 10 倍量乙醇溶解，加活性炭脱色，重结晶一次，得妊烯醇酮。

文献信息

• Azasteroids for treatment of tuberculosis
  申请人：The Research Foundation for the State University of New York

  公开号：US11072633B2

  公开（公告）日：2021-07-27

  The present invention provides a compound having the structure: for use in combination with an anti-tuberculosis drug for treating a subject infected with M. tuberculosis.

  本发明提供了一种具有以下结构的化合物： 用于与抗结核药物联合使用，治疗感染结核杆菌的患者。
• USE OF FINASTERIDE, DUTASTERIDE AND RELATED COMPOUNDS FOR THE PREVENTION OR TREATMENT OF NEUROLOGICALLY-ASSOCIATED DISORDERS
  申请人：Soskic Vukic

  公开号：US20090170889A1

  公开（公告）日：2009-07-02

  The present invention relates to new pharmaceutical uses of 4-azasteroid compounds, in particular of Finasteride/Dutasteride/Dutasteride and Dutasteride, particularly preferred of Finasteride/Dutasteride/Dutasteride, and its pharmaceutically acceptable derivatives, and combinations comprising said compounds. The invention also features generally the use of a modulator compound of neuroprotective conditions via beta subunits of shaker-type voltage-gated potassium channels and/or via members of solute carriers family 25, in particular Aralar (member 12) and adenine-nucleotide translocators 1 & 2 (member 4 & 5) and/or via a 4-nitrophenylphosphatase domain and non-neuronal SNAP25-like protein homolog 1 (NIPSNAP 1) as a neuroprotective medicament, particularly as a medicament for the prevention and/or treatment of neurological diseases such as dementia, Parkinson, Alzheimer, schizophrenia or epilepsy. The demonstrated inhibition of the MPTP appears to constitute a novel principle applicable to all pathological conditions which have underlying excitotoxic/mitochondrial mechanisms, like: amyotrophic lateral sclerosis, Alzheimer's disease, depression, epilepsy, multiple sclerosis, pain, Parkinson's disease, schizophrenia, traumatic brain and spinal chord injury, stroke and other ischemic conditions in the brain.
• STEROL SIDE CHAIN-CLEAVING ENZYME PROTEIN AND USE THEREOF
  申请人：Yamagishi Masahiro

  公开号：US20120178124A1

  公开（公告）日：2012-07-12

  It is an object of the present invention to obtain highly active P450scc enzyme protein which is an important enzyme protein that catalyzes the first step of the biosynthesis of industrially useful steroid hormone. The present invention provides a sterol side chain cleavage enzyme protein having the following physicochemical properties: (1) action: the enzyme acts on sterol represented by formula (I) as defined in the specification and cleaves the carbon-carbon bond between positions 20 and 22 of a sterol side chain portion by its activity of cleaving the bonds, so as to generate a compound represented by formula (II) as defined in the specification; (2) substrate specificity: when microorganisms that produce the enzyme protein are allowed to react with an aqueous solution containing 100 μg/ml 4-cholesten-3-one or cholesterol at 28° C. for 5 hours, the conversion reaction rate from 4-cholesten-3-one to progesterone is 10% or more, and the conversion rate from cholesterol to pregnenolone is 10% or more;
• AZASTEROIDS FOR TREATMENT OF TUBERCULOSIS
  申请人：The Research Foundation for the State University of New York

  公开号：US20190161514A1

  公开（公告）日：2019-05-30

  The present invention provides a compound having the structure: for use in combination with an anti-tuberculosis drug for treating a subject infected with M. tuberculosis.
• US7998970B2
  申请人：——

  公开号：US7998970B2

  公开（公告）日：2011-08-16