(3B)-3-羟基-胆甾-5-烯-22-酮 | 19243-30-2

• 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: (3B)-3-羟基-胆甾-5-烯-22-酮
• 英文名称: 3β-hydroxycholest-5-en-22-one
• 英文别名: 22-keto-cholesterol；22-ketocholesterol；22-oxocholesterol；3β-hydroxy-cholest-5-en-22-one；3β-Hydroxy-cholest-5-en-22-on；3β-Hydroxycholest-5-en-22-on；(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-one
• CAS: 19243-30-2
• 化学式: C₂₇H₄₄O₂
• mdl: MFCD07357246
• 分子量: 400.645
• InChiKey: ZJIBAMHOAQWYSE-CNXJXGGASA-N

物化性质

• 熔点：
  142.5-143.5 °C
• 沸点：
  508.5±23.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• 保留指数：
  3255

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3B)-3-羟基-胆甾-5-烯-22-酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 cholest-5-ene-3β,22R-diol
  参考文献：
  名称：

  在牛肾上腺皮质制剂中抑制胆固醇向孕烯醇酮的转化。

  摘要：

  在牛肾上腺皮质线粒体乙缩醛制剂中，已研究了多种类固醇对[4-14C]胆固醇向[4-14C]孕烯醇酮转化的抑制作用。在等摩尔底物和抑制剂浓度（3.3μM）下，最有效的抑制剂是胆固醇衍生物，其在c-22处具有氮官能，其次是衍生物在c-22或c-20处或两者具有氧官能。c-17处羟基的存在或氟对3β-羟基的取代降低了抑制效力。在抑制剂也是胆固醇侧链裂解系统的良好底物的情况下，例如某些胆固醇衍生物在侧链中被羟基化，[4-14C]孕烯醇酮的形成速率随时间的增加而增加。 。（20S）-20，21-二羟基胆固醇对[4-14C]孕烯醇酮的形成动力学产生了这样的影响，并且产生了21-羟基孕烯醇酮，其通过气相色谱-质谱法鉴定。描述了（20R）-22-酮胆固醇，（20R，22R）-22-羟基胆固醇，（20R，22S）-羟基胆固醇和（20S）-去甾醇的合成。

  DOI：

  10.1016/0039-128x(76)90057-x
• 作为产物：
  描述：

  magnesium,2-methylbutane,bromide 在 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 47.5h， 生成 (3B)-3-羟基-胆甾-5-烯-22-酮
  参考文献：
  名称：

  Regulation of liver X receptor target genes by 22-functionalized oxysterols. Synthesis, in silico and in vitro evaluations

  摘要：

  The endogenous oxysterol 22(R)-hydroxycholesterol (22RHC, 1) is an LXR agonist which upregulates genes of critical involvement in human cholesterol- and lipid metabolism. In contrast, its synthetic epimer 22(S)-hydroxycholesterol (22SHC, 8) has shown specific antagonistic effects in recent studies, avoiding unwanted side effects provided by potent LXR agonists. In terms of LXR modulation, the aim of this study was to compare 22SHC (8), 22RHC (1) and synthesized ligands with keto- and amide functionality in the 22nd position of the cholesterol scaffold. 22SHC (8) and 22RHC (1) performed as expected while 22-ketocholesterol (22KC, 10) revealed an attractive in vitro profile for further investigation in terms of anti-atherosclerotic properties as selective upregulation of the ATP-binding cassette transporter ABCA1 was observed. A new synthesized amide derivate, Fernholtz cyclohexylamide (13) was shown to reduce lipogenesis in a dose-responsive manner and abolish the effect of the potent LXR agonist T0901317 when administered simultaneously. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.12.003

文献信息

• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• Process for producing steroid compounds having an oxogroup in the side chain
  申请人：TEIJIN LIMITED

  公开号：EP0013082A1

  公开（公告）日：1980-07-09

  A process for producing a steroid compound having an oxo group in the side chain, which comprises condensing an acid halide having a steroid skeleton with an organozinc compound at a halocarbonyl group of the acid halide in an inert organic medium in the presence of a catalytic amound of an ether capable of forming a complex with the organozinc compound and, if desired, hydrolyzing the product. The process gives the steroid compound in a high yield, and often in an almost quantitative yield. The steroid compound can be an important intermediate for the production of vitamin D3 analogs, such as active forms of vitamin D3.

  一种生产侧链中含有氧代基团的甾体化合物的工艺，包括在惰性有机介质中，在能与有机锌化合物形成络合物的醚的催化下，在酸卤化物的卤代羰基上将具有甾体骨架的酸卤化物与有机锌化合物缩合，并在需要时水解产物。该工艺可以得到高产率的甾体化合物，通常几乎可以达到定量产率。类固醇化合物可以作为生产维生素 D3 类似物（如活性维生素 D3）的重要中间体。
• METHOD OF ASSAYING OXIDIZED LDL-BETA 2-GLYCOPROTEIN I COMPLEX IN VIVO
  申请人：Matsuura, Eiji

  公开号：EP1548436A1

  公开（公告）日：2005-06-29

  A complex having oxLDL bound covalently to β2-GPI can be used as a standard for measuring a β2-GPI/oxLDL complex in the living body thereby measuring the β2-GPI/oxLDL complex in the living body more accurately and strictly, and can be utilized to provide a new measurement method, detection method, kit etc.

  氧化LDL 与 β2-GPI 共价结合的复合物可用作测量活体内 β2-GPI/oxLDL 复合物的标准，从而更准确、更严格地测量活体内的 β2-GPI/oxLDL 复合物，并可用于提供新的测量方法、检测方法、试剂盒等。
• Constructs and methods for biosynthesis of cyclopamine
  申请人：Donald Danforth Plant Science Center

  公开号：US11001850B2

  公开（公告）日：2021-05-11

  The present disclosure relates generally to the identification of enzymes within the cyclopamine biosynthesis pathway as well as to engineering transgenic plants or organisms for the production of cyclopamine.

  本公开总体上涉及环丙胺生物合成途径中酶的鉴定以及用于生产环丙胺的转基因植物或生物工程。