3β,27-dihydoxycholest-5-en-7-one | 148988-28-7

• 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,27-dihydoxycholest-5-en-7-one
• 英文别名: 27-hydroxy-7-ketocholesterol；27-Hydroxy-7-keto Cholesterol；(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-17-[(2R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 148988-28-7
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: LFNAJBFFWWMSEW-ANDJGGKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 在 dirhodium(II) tetrakis(caprolactam) 叔丁基过氧化氢 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以60%的产率得到3β,27-dihydoxycholest-5-en-7-one
  参考文献：
  名称：

  Optimal TBHP Allylic Oxidation of Δ⁵-Steroids Catalyzed by Dirhodium Caprolactamate

  摘要：

  Dirhodium caprolactamate is the most efficient catalyst for the oxidation of Delta(5)-steroids to 7-keto-Delta(5)-steroids by 70% tert-butyl hydroperoxide in water (T-HYDRO). Isolated product yields range from 38 to 87%.

  DOI：

  10.1021/ol7025284

文献信息

• [EN] INHIBITION OF PPAR GAMMA EXPRESSION IN PREADIPOCYTE CELLS BY OXYSTEROLS<br/>[FR] INHIBITION DE L'EXPRESSION DES PPAR GAMMA DANS LES CELLULES PRÉADIPOCYTAIRES AU MOYEN D'OXYSTÉROLS
  申请人：UNIV CALIFORNIA

  公开号：WO2011006087A1

  公开（公告）日：2011-01-13

  This invention relates, e.g., to methods and agents to inhibit peroxisome proliferator activated receptor expression (PPAR) in preadipocytes.

  这项发明涉及抑制脂肪前体细胞中过氧化物酶体增殖激活受体表达（PPAR）的方法和药剂。
• Novel class of sterol ligands and their uses in regulation of cholesterol and gene expression
  申请人：Javitt B. Norman

  公开号：US20060121024A1

  公开（公告）日：2006-06-08

  This invention relates to oxysteroids and oxysteroid hormones which have been identified. These oxysteroids are C27 modified sterols, particularly derivatives of intermediates in cholesterol synthesis, including lanosterol, zymosterol and desmosterol, including C27 diol and C27 acid derivatives, as well as related compounds and analogs thereof. The oxysteroids are capable of binding to or otherwise interacting with orphan nuclear receptors to result in modulation of gene expression. The invention further relates to methods of modulating the rate of cholesterol synthesis in a mammal. More specifically, the invention relates to treatment of cholesterol-related conditions which are improved or ameliorated by modulating the rate of cholesterol synthesis or cholesterol metabolism in a human in need thereof by administration of these oxysteroids, analogs or antagonists thereof. The invention includes methods for ameliorating, treating or preventing macular degeneration in a mammal comprising administering to said mammal an agent which stimulates or enhances the expression or activity of steroid sulphotransferase (SLUT2), particularly SLUT2B1b, or which stimulates or enhances the expression or activity of CYP27A1 or sterol 27-hydroxylase or otherwise increasing the sulfonation or 27-hydroxylation of cholesterol intermediates, including 7-ketocholesterol. Assays for identification of analogs, antagonists or modulators of these oxysteroids or of sterol 27-hydroxylase are also provided.

  本发明涉及已经鉴定的氧化甾体和氧化甾体激素。这些氧化甾体是C27修饰类固醇，特别是胆固醇合成中间体的衍生物，包括鲸蜡醇、酵母蜡醇和脱酸酶醇，包括C27二醇和C27酸衍生物，以及相关化合物和类似物。这些氧化甾体能够与孤儿核受体结合或以其他方式相互作用，从而调节基因表达。本发明进一步涉及在哺乳动物中调节胆固醇合成速率的方法。更具体地，本发明涉及通过给予这些氧化甾体、类似物或其拮抗剂来改善或缓解需要调节胆固醇合成或胆固醇代谢速率的人类的与胆固醇相关的疾病的治疗。本发明包括治疗、改善或预防哺乳动物黄斑退化的方法，包括给予一种刺激或增强类固醇硫酸转移酶（SLUT2），特别是SLUT2B1b，表达或活性的药物，或者刺激或增强CYP27A1或类固醇27-羟化酶的表达或活性，或以其他方式增加胆固醇中间体的磺酸化或27-羟化，包括7-酮胆固醇。还提供了用于鉴定这些氧化甾体或类固醇27-羟化酶的类似物、拮抗剂或调节剂的测定方法。
• Oxysterol Compounds and the Hedgehog Pathway
  申请人：Parhami Farhad

  公开号：US20100034781A1

  公开（公告）日：2010-02-11

  This invention relates, for example, to synthetic oxysterols. Also described are methods for using the compounds, including treating subjects in need thereof, and pharmaceutical compositions and kits for implementing methods of the invention.

  本发明涉及合成氧化甾醇，例如。还描述了使用这些化合物的方法，包括治疗需要的受体，以及实施本发明方法的药物组合物和工具包。
• INHIBITION OF PPAR GAMMA EXPRESSION BY SPECIFIC OSTEOGENIC OXYSTEROLS
  申请人：Parhami Farhad

  公开号：US20100105645A1

  公开（公告）日：2010-04-29

  This invention relates to methods for using agents to inhibit peroxisome proliferator activated receptor expression.

  本发明涉及使用药剂抑制过氧化物酶体增殖激活受体表达的方法。
• Liposomal formulation of nonglycosidic ceramides and uses thereof
  申请人：LUDWIG INSTITUTE FOR CANCER RESEARCH LTD.

  公开号：US10039715B2

  公开（公告）日：2018-08-07

  The invention provides liposomes containing nonglycosidic ceramides within their bilayers, and compositions thereof. These liposomes activate murine iNKT cells and induce dendritic cell (DC) maturation, both in vitro and in vivo at an efficacy that is comparable to their corresponding soluble nonglycosidic ceramides. Also provided are methods for treating diseases using the liposomes and compositions of the invention.

  本发明提供了在其双层内含有非糖苷类神经酰胺的脂质体及其组合物。这些脂质体可在体外和体内激活小鼠 iNKT 细胞并诱导树突状细胞（DC）成熟，其功效与相应的可溶性非糖苷神经酰胺相当。此外，还提供了使用本发明脂质体和组合物治疗疾病的方法。