(R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-(piperidin-1-yl)pentan-1-one | 241139-67-3

• 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: (R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-(piperidin-1-yl)pentan-1-one
• 英文别名: 3β-hydroxychol-5(6)-enic acid piperidine amide；(4R)-4-[(3S,8S,9S,10R,13R,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]-1-piperidin-1-ylpentan-1-one
• CAS: 241139-67-3
• 化学式: C₂₉H₄₇NO₂
• 分子量: 441.698
• InChiKey: HQEOOEBPIAQBCV-OHPSOFBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到(R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-(piperidin-1-yl)pentan-1-one
  参考文献：
  名称：

  胆碱酰胺衍生物作为LXR配体的结构要求。

  摘要：

  对胆酸衍生物作为肝X受体（LXR）配体的结构要求进行了研究。与LXR络合的胆酰胺衍生物1的模型显示，C24羰基氧与位于Trp457附近的His435形成氢键。N，N-二甲基位于疏水口袋中。基于这些数据，我们设计了对LXR具有高亲和力的化合物。由3β-乙酰基-Δ5-胆酸20合成胆酰胺衍生物1-11，由醇25合成内酰胺12-19。在报告基因分析中，叔酰胺3和4表现出更高的活性，具有疏水残基的化合物表现出最高的活性所有衍生品。发现C23的立体化学是EC50和基因反式激活的重要决定因素，因为每种异构体均表现出不同的活性。

  DOI：

  10.1016/j.bmcl.2019.03.051

文献信息

• STEROL ANALOGS AND USES THEREOF
  申请人：ModernaTX, Inc.

  公开号：US20220402965A1

  公开（公告）日：2022-12-22

  The invention relates to compositions and methods for the preparation, manufacture, and therapeutic use of compositions comprising mRNA and a lipid nanoparticle comprising a compound of the invention and an ionizable lipid.

  本发明涉及包含mRNA和脂质纳米粒子的组合物的制备、制造和治疗用途的方法和组合物，所述脂质纳米粒子包括本发明的化合物和可离子化脂质。
• COMPOSITIONS AND METHODS FOR DELIVERY OF AGENTS TO IMMUNE CELLS
  申请人：ModernaTX, Inc.

  公开号：US20190314291A1

  公开（公告）日：2019-10-17

  The disclosure features immune cell delivery lipid nanoparticle (LNP) compositions that allow for enhanced delivery of agents, e.g., nucleic acids, such as therapeutic and/or prophylactic RNAs, to immune cells, in particular T cells, as well as B cells, dendritic cells and monocytes. The LNPs comprise an effective amount of an immune cell delivery potentiating lipid such that delivery of an agent by an immune cell delivery LNP is enhanced as compared to an LNP lacking the immune cell delivery potentiating agent. Methods of using the immune cell delivery LNPs for delivery of agents, e.g., nucleic acid delivery, for protein expression, for modulating immune cell activity and modulating immune responses are also disclosed.
• [EN] COMPOSITIONS AND METHODS FOR DELIVERY OF AGENTS TO IMMUNE CELLS<br/>[FR] COMPOSITIONS ET PROCÉDÉS DESTINÉS À L'ADMINISTRATION D'AGENTS À DES CELLULES IMMUNITAIRES
  申请人：MODERNATX INC

  公开号：WO2019152557A1

  公开（公告）日：2019-08-08

  The disclosure features immune cell delivery lipid nanoparticle (LNP) compositions that allow for enhanced delivery of agents, e.g., nucleic acids, such as therapeutic and/or prophylactic RNAs, to immune cells, in particular T cells, as well as B cells, dendritic cells and monocytes. The LNPs comprise an effective amount of an immune cell delivery potentiating lipid such that delivery of an agent by an immune cell delivery LNP is enhanced as compared to an LNP lacking the immune cell delivery potentiating agent. Methods of using the immune cell delivery LNPs for delivery of agents, e.g., nucleic acid delivery, for protein expression, for modulating immune cell activity and modulating immune responses are also disclosed.
• [EN] STEROL ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES DE STÉROL ET LEURS UTILISATIONS
  申请人：MODERNATX INC

  公开号：WO2020061332A1

  公开（公告）日：2020-03-26

  The invention relates to compositions and methods for the preparation, manufacture, and therapeutic use of compositions comprising mRNA and a lipid nanoparticle comprising a compound of the invention and an ionizable lipid.
• [EN] DIFFERENTIALLY EXPRESSED IMMUNE CELL MICRORNAS FOR REGULATION OF PROTEIN EXPRESSION<br/>[FR] MICROARN DE CELLULES IMMUNITAIRES EXPRIMÉS DE MANIÈRE DIFFÉRENTIELLE POUR LA RÉGULATION DE L'EXPRESSION DE PROTÉINES
  申请人：MODERNATX INC

  公开号：WO2020227537A1

  公开（公告）日：2020-11-12

  The disclosure features mRNAs engineered with one or more microRNA binding sites targeted by a microRNA(s) that are differentially expressed in a target immune cell relative to a plurality of non-target immune cells. The disclosure also features methods of using the same, for example, for selectively degrading the mRNA in the target immune cell relative to the plurality of non-target immune cells.