20α,22R-dihydroxycholesterol

• 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: 20α,22R-dihydroxycholesterol
• 英文别名: 20,22-Dihydroxycholesterol；(2R)-2-[(3S,8S,9S,10R,13S,14S,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]-6-methylheptane-2,3-diol
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: ISBSSBGEYIBVTO-SDRJTJMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cholesterol 20α-hydroperoxide 在 bovine recombinant cytochrome P₄₅₀ 11-hydroxylase 作用下， 生成 20α,22R-dihydroxycholesterol
  参考文献：
  名称：

  胆固醇氢过氧化物作为胆固醇代谢的细胞色素P450酶的底物以及25-羟基胆固醇和其他氧固醇的替代来源

  摘要：

  据报道，胆固醇的主要自氧化产物（即25和20ξ-氢过氧化物）与四种主要的胆固醇代谢细胞色素P450酶之间存在相互作用。在酶CYP27A1和CYP11A1中添加25-氢过氧化胆固醇会引起明确的光谱变化，同时产生25-羟基胆固醇作为主要产物。CYP27A1和CYP11A1中20ξ-氢过氧化物诱导的光谱移动，但仅使用CYP11A1检测到乙二醇代谢产物。CYP7A1和CYP46A1不能与任何氢过氧化物产生代谢物。提出了P450氢过氧化物分流反应，其中氢过氧化物既充当还原性氧的供体，又充当底物。CYP27A1被证明可介导将25-氢过氧化胆固醇还原为25-羟基胆固醇，对于具有高氧化应激的富含胆固醇的组织具有潜在意义。CYP27A1可能参与这些组织中有害自氧化产物的清除，同时提供25-羟基胆固醇的补充来源，25-羟基胆固醇是免疫细胞功能的调节剂和病毒细胞进入的介质。

  DOI：

  10.1002/anie.201505002

文献信息

• [EN] DESIGN AND SYNTHESIS OF OPTIMIZED LIGANDS FOR PPAR<br/>[FR] CONCEPTION ET SYNTHESE DE LIGANDS OPTIMISE POUR PPAR
  申请人：BETHESDA PHARMACEUTICALS INC

  公开号：WO2005009437A1

  公开（公告）日：2005-02-03

  This invention provides new chemical entities useful for treating a variety of clinical disorders including those that areinfluenced by the activity of peroxisome proliferator activated receptors (PPAR). The structures of the compounds and methods to design, make and use the compounds are provided. Compounds and methods for administering therapeutic compositions comprising the compounds in cases of the disease psoriasis are provided. An exemplary compound having the formula compound is 5­adamantan-2-yl-pentanoic acid 2-[4-(2,4-dioxo-thiazolidin-5-yl-methyl)-phenoxy]-ethyl}-methyl-amide is provided.

  这项发明提供了新的化学实体，可用于治疗各种临床疾病，包括那些受过氧化物酶体增殖物激活受体（PPAR）活性影响的疾病。提供了这些化合物的结构以及设计、制造和使用这些化合物的方法。提供了在牛皮癣病例中使用这些化合物的治疗组合物的化合物和方法。提供了一个具有以下结构的示例化合物：5-金刚烷基-2-基戊酸2-[4-(2,4-二氧-噻唑啉-5-基-甲基)-苯氧基]-乙基}-甲基酰胺。
• [EN] LIGANDS THAT MODULATE LXR-TYPE RECEPTORS<br/>[FR] LIGANDS MODULANT DES RECEPTEURS DU TYPE LXR
  申请人：GALDERMA RES & DEV

  公开号：WO2004076418A1

  公开（公告）日：2004-09-10

  The invention relates to novel compounds that are ligands of the LXR receptors, corresponding to the general formula (I) below also to the method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine, or alternatively in cosmetic compositions.

  本发明涉及新型化合物，它们是LXR受体的配体，对应于下面的通式（I），以及它们的制备方法和它们在制备用于人类或兽医药物、或者化妆品组合物的药物组合物中的使用。
• Compounds that act to modulate insect growth and methods and systems for identifying such compounds
  申请人：Henrich C. Vincent

  公开号：US20050049230A1

  公开（公告）日：2005-03-03

  Disclosed are methods and systems for screening for compounds that act to modulate insect growth. Bioassays including cell culture and/or transgenic insects engineered with various components of the ecdysoid receptor (EcR) and/or the farsenoid-X receptor (RXR) systems to identify compounds that act as insecticides and/or hormone receptor activators are described. Also described are compounds, and compositions, identified as being putative insecticides based upon their ability to activate EcR and/or FXR mediated transcription.

  本发明涉及筛选调节昆虫生长的化合物的方法和系统。描述了生物测定法，包括细胞培养和/或转基因昆虫，这些昆虫经过工程改造，具有ecdysoid受体（EcR）和/或farsenoid-X受体（RXR）系统的各种组分，以识别作为杀虫剂和/或激素受体激活剂的化合物。还描述了被鉴定为潜在杀虫剂的化合物和组合物，这些化合物和组合物的鉴定基于它们激活EcR和/或FXR介导的转录的能力。
• Novel ligands that modulate LXR-type receptors and cosmetic/pharmaceutical applications thereof
  申请人：Diaz Philippe

  公开号：US20060058351A1

  公开（公告）日：2006-03-16

  Novel compounds that are ligands of the LXR receptors have the following structural formula (I): and are formulated into pharmaceutical compositions useful in human or veterinary medicine, or alternatively into cosmetic compositions.

  具有以下结构式(I)的配体LXR受体的新化合物，可制成在人类或兽医学中有用的药物组合物，或者制成化妆品组合物。
• Compounds That Act To Modulate Insect Growth And Methods And Systems For Identifying Such Compounds
  申请人：Henrich Vincent C.

  公开号：US20110207707A1

  公开（公告）日：2011-08-25

  Disclosed are methods and systems for screening for compounds that act to modulate insect growth. Bioassays including cell culture and/or transgenic insects engineered with various components of the ecdysoid receptor (EcR) and/or the farsenoid-X receptor (RXR) systems to identify compounds that act as insecticides and/or hormone receptor activators are described. Also described are compounds, and compositions, identified as being putative insecticides based upon their ability to activate EcR and/or FXR mediated transcription.

  本发明涉及筛选调节昆虫生长的化合物的方法和系统。本发明描述了生物测定方法，包括细胞培养和/或转基因昆虫，这些昆虫经过工程设计，具有各种成分的ecdysoid受体（EcR）和/或farsenoid-X受体（RXR）系统，以识别作为杀虫剂和/或激素受体激活剂的化合物。本发明还描述了通过其激活EcR和/或FXR介导的转录而被认为是杀虫剂的化合物和组合物。