4-((1R,2R)-2-amino-1-hydroxy-3-(pyrrolidin-1-yl)propyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-((1R,2R)-2-amino-1-hydroxy-3-(pyrrolidin-1-yl)propyl)phenol
• 英文别名: 4-[(1R,2R)-2-amino-1-hydroxy-3-pyrrolidin-1-ylpropyl]phenol
• 化学式: C₁₃H₂₀N₂O₂
• 分子量: 236.314
• InChiKey: GEBNUWSIEIBNRX-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  69.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((1R,2R)-2-amino-1-hydroxy-3-(pyrrolidin-1-yl)propyl)phenol 在 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-((1R,2R)-1-(4-(cyclopropylmethoxy)phenyl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2-(2,3-dihydro-1H-inden-2-yl)acetamide
  参考文献：
  名称：

  [EN] GLUCOSYLCERAMIDE SYNTHASE INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  [FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE ET MÉTHODES THÉRAPEUTIQUES LES UTILISANT

  摘要：

  公开号：

  WO2016126572A3

文献信息

• Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors
  申请人：Genzyme Corporation

  公开号：US20030050299A1

  公开（公告）日：2003-03-13

  Disclosed is a novel enantiomeric synthesis cermamide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

  披露了一种新型对映合成UDP葡萄糖：N-酰基鞘氨醇葡糖转移酶抑制剂的方法。同时还披露了在合成过程中形成的新型中间体。
• SYNTHESIS OF UDP-GLUCOSE: N-ACYLSPHINGOSINE GLUCOSYL TRANSFERASE INHIBITORS
  申请人：GENZYME CORPORATION

  公开号：US20150148534A1

  公开（公告）日：2015-05-28

  Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

  本发明揭示了一种新的手性合成UDP-葡萄糖：N-酰基鞘氨醇葡萄糖基转移酶抑制剂。同时还揭示了在合成过程中形成的新型中间体。
• 2-acylaminopropanol-type glucosylceramide synthase inhibitors
  申请人：Genzyme Corporation

  公开号：EP2594562A2

  公开（公告）日：2013-05-22

  A compound is represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. A pharmaceutical composition comprises a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. A method of treating a subject in need thereof comprises administering to the subject a therapeutically effective amount of a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The subject has type 2 diabetes; renal hypertrophy or hyperplasia associated with diabetic nephropathy; Tay-Sachs; Gaucher's or Fabry's disease. Methods of decreasing plasma TNF-α, lowering blood glucose levels, decreasing glycated hemoglobin levels, inhibiting glucosylceramide synthase, and lowering glycosphingolipid concentration in a subject in need thereof respectively comprise administering to the subject a therapeutically effective amount of a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof.

  一种化合物由结构式 (I) 代表：或其药学上可接受的盐。一种药物组合物包含由结构式（I）代表的化合物或其药学上可接受的盐。一种治疗有需要的受试者的方法，包括向受试者施用治疗有效量的结构式（I）所代表的化合物或其药学上可接受的盐。受试者患有 2 型糖尿病；与糖尿病肾病相关的肾肥大或增生；Tay-Sachs；Gaucher 或 Fabry 病。降低血浆TNF-α、降低血糖水平、降低糖化血红蛋白水平、抑制葡萄糖酰甘油酰胺合成酶和降低糖磷脂浓度的方法包括向有需要的受试者分别施用治疗有效量的由结构式(I)代表的化合物或其药学上可接受的盐。
• Glucosylceramide synthase inhibitors and therapeutic methods using the same
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US10202340B2

  公开（公告）日：2019-02-12

  Glucosylceramide synthase inhibitors and compositions containing the same are disclosed. Methods of using the glucosylceramide synthase inhibitors in the treatment of diseases and conditions wherein inhibition of glucosylceramide synthase provides a benefit, like Gaucher disease and Fabry disease, also are disclosed.

  本发明公开了葡萄糖酰胺合成酶抑制剂和含有这些抑制剂的组合物。还公开了使用葡萄糖基甘油酰胺合成酶抑制剂治疗疾病和病症的方法，在这些疾病和病症中，抑制葡萄糖基甘油酰胺合成酶会带来益处，如戈谢病和法布里病。
• EP3253734B1
  申请人：——

  公开号：EP3253734B1

  公开（公告）日：2020-12-23