(3beta,5alpha)-麦角甾烷-3-醇 | 6538-02-9

• 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: (3beta,5alpha)-麦角甾烷-3-醇
• 中文别名: 麥角甾烷醇
• 英文名称: ergostanol
• 英文别名: campestanol；24S-methyl-5α-cholestan-3β-ol；(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 6538-02-9
• 化学式: C₂₈H₅₀O
• 分子量: 402.704
• InChiKey: ARYTXMNEANMLMU-OZEQXKMUSA-N

物化性质

• 熔点：
  144-145°
• 比旋光度：
  D20 +15.9° (c = 1.8 in chloroform)
• 沸点：
  464.78°C (rough estimate)
• 密度：
  0.9476 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3beta,5alpha)-麦角甾烷-3-醇 生成 5α-ergostanyl-(3β)-palmitate
  参考文献：
  名称：

  Oleson et al., Journal of Biological Chemistry, 1947, vol. 171, p. 1,3

  摘要：

  DOI：
• 作为产物：
  描述：

  ergost-22-en-3-one 在 乙酸乙酯 、 铂 作用下， 生成 (3beta,5alpha)-麦角甾烷-3-醇
  参考文献：
  名称：

  380.分子旋转差异法在类固醇上的应用。第十部分“ β-二氢麦角固醇”。

  摘要：

  DOI：

  10.1039/jr9490001771

文献信息

• Facile Barton−McCombie Deoxygenation of Alcohols with Tetrabutylammonium Peroxydisulfate and Formate Ion
  作者：Hee Sock Park、Hee Yoon Lee、Yong Hae Kim

  DOI：10.1021/ol050886h

  日期：2005.7.1

  [reaction: see text]. A new method for efficient radical deoxygenation of alcohols is described for preparing bulk chemicals avoiding scale-up problems. Treatment of various thiocarbonyl derivatives with (Bu(4)N)(2)S(2)O(8) and HCO(2)Na in DMF afforded the corresponding deoxygenated products in excellent yields. The deoxygenation appears to be initiated by the transfer of a single electron to thiocarbonyl

  [反应：请参见文字]。描述了一种用于醇的有效自由基脱氧的新方法，用于制备散装化学品以避免规模扩大的问题。用（Bu（4）N）（2）S（2）O（8）和HCO（2）Na在DMF中处理各种硫代羰基衍生物以优异的收率提供了相应的脱氧产物。脱氧似乎是由单个电子从CO（2）（*）（-）而不是SO4（*）（-）转移到硫代羰基衍生物而引发的。
• Novel sterol/stanol phosphorylnitroderivatives and use thereof in treating or preventing cardiovascular disease, its underlying conditions and other disorders
  申请人：Orchansky Liliana Patricia

  公开号：US20070232688A1

  公开（公告）日：2007-10-04

  Sterol and stanol phosphorylnitro derivatives and their use in treating or preventing cardiovascular disease, its underlying conditions and other disorders are disclosed. The disclosed compounds include a phosphate linker, at least one moiety that releases nitric oxide (NO), and a sterol or stanol moiety. Some compounds additionally include an ascorbyl moiety to make the compound more readily soluble in aqueous and non-aqueous media.

  甾醇和甾酚磷酸硝基衍生物及其在治疗或预防心血管疾病、其潜在病症和其他疾病中的用途被披露。所披露的化合物包括一个磷酸酯连接物、至少一个释放一氧化氮（NO）的基团，以及一个甾醇或甾酚基团。一些化合物还包括抗坏血酸基团，以使化合物在水性和非水性介质中更容易溶解。
• [EN] DERIVATIVES COMPRISING STEROLS AND/OR STANOLS AND SPECIFIC CLASSES OF ANTI-INFLAMMATORY AGENTS AND USE THEREOF IN TREATING OR PREVENTING CARDIOVASCULAR DISEASE<br/>[FR] DERIVES COMPRENANT DES STEROLS ET/OU DES STANOLS ET DES CLASSES SPECIFIQUES D'AGENTS ANTI-INFLAMMATOIRES, ET UTILISATION DESDITS DERIVES POUR LE TRAITEMENT OU LA PREVENTION DE MALADIES CARDIOVASCULAIRES
  申请人：FORBES MEDI TECH INC

  公开号：WO2004029068A1

  公开（公告）日：2004-04-08

  The present invention provides, in one aspect, novel derivatives comprising sterols and/or stanols and an NSAID selected from salicylic acids and arylalkanoic acids, including salts of these derivatives, and having one or more of the following formulae: a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) formula (I), wherein R is a sterol or stanol moiety, R2 is derived from a salicylic acid or an arylalkanoic acid and n=1-5. Also provided are pharmaceutical compositions comprising one or more of these novel derivatives and methods of treating or preventing cardiovascular disease and its underlying conditions including, without limitation, atherosclerosis, hypercholesterolemia, hyperlipidemia, hypertension, thrombosis, coronary artery disease, and for treating and reducing inflammation including coronary plaque inflammation, bacterial-induced inflammation, viral induced inflammation and inflammation associated with acute pain and surgical procedures which comprises administering to an animal, particularly a human, a non-toxic and therapeutically effective amount of one or more of these compounds or a biologically acceptable salt thereof.

  本发明一方面提供了新颖的衍生物，包括甾醇和/或甾烷醇以及从水杨酸和芳烷酸中选择的非甾体抗炎药（NSAID），包括这些衍生物的盐，并具有以下一种或多种公式：a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) 公式 (I)，其中R是甾醇或甾烷醇部分，R2来自水杨酸或芳烷酸，n=1-5。还提供了包含一种或多种这些新颖衍生物的药物组合物，以及治疗或预防心血管疾病及其基础条件的方法，包括但不限于动脉粥样硬化、高胆固醇血症、高脂血症、高血压、血栓形成、冠心病，以及治疗和减少炎症的方法，包括冠状动脉斑块炎症、细菌诱导的炎症、病毒诱导的炎症以及与急性疼痛和手术程序相关的炎症，该方法包括向动物，尤其是人类，投予一种或多种这些化合物或其生物学可接受的盐的非毒性和治疗有效量。
• FORMULATIONS FOR THE DELIVERY OF ACTIVE AGENTS TO INSECTS, PLANTS, AND PLANT PATHOGENS
  申请人：Preceres Inc.

  公开号：US20170325457A1

  公开（公告）日：2017-11-16

  The present disclosure is directed to formulations comprising (1) at least one formulation transport agent, (2) at least one complexing agent, and (3) at least one active agent that modulates one or more traits of a target insect, plant, or plant pathogen. The present disclosure is also directed to methods of delivering such formulations to the target organism, as well as to formulation transport agents used to prepare such formulations.

  本公开涉及包含（1）至少一种制剂运输剂、（2）至少一种络合剂和（3）至少一种调节目标昆虫、植物或植物病原体的一个或多个特征的活性剂的配方。本公开还涉及将这种配方传递给目标生物体的方法，以及用于制备这种配方的制剂运输剂。
• Marine and Semi-Synthetic Hydroxysteroids as New Scaffolds for Pregnane X Receptor Modulation
  作者：Valentina Sepe、Francesco Di Leva、Claudio D'Amore、Carmen Festa、Simona De Marino、Barbara Renga、Maria D'Auria、Ettore Novellino、Vittorio Limongelli、Lisette D'Souza、Mahesh Majik、Angela Zampella、Stefano Fiorucci

  DOI：10.3390/md12063091

  日期：——

  In recent years many sterols with unusual structures and promising biological profiles have been identified from marine sources. Here we report the isolation of a series of 24-alkylated-hydroxysteroids from the soft coral Sinularia kavarattiensis, acting as pregnane X receptor (PXR) modulators. Starting from this scaffold a number of derivatives were prepared and evaluated for their ability to activate

  近年来，已从海洋来源中鉴定出许多具有不寻常结构和有希望的生物特征的甾醇。在这里，我们报告了从软珊瑚 Sinularia kavarattiensis 中分离出一系列 24-烷基化羟基类固醇，作为孕烷 X 受体 (PXR) 调节剂。从该支架开始，制备了许多衍生物，并通过评估反式激活和量化基因表达来评估它们激活 PXR 的能力。我们的研究表明，ergost-5-en-3β-ol (4) 在 HepG2 细胞中诱导 PXR 反式激活并刺激 PXR 靶基因 CYP3A4 的表达。为了阐明这些配体与 PXR 之间相互作用的分子基础，我们通过对接模拟研究了该系列中最有效的化合物 4 与 PXR 的结合机制。