(2R,3R,4R,5S)-2-(hydroxymethyl)-1-(3-(3-propoxyphenyl)propyl)piperidine-3,4,5-triol | 1383152-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-(3-(3-propoxyphenyl)propyl)piperidine-3,4,5-triol
• 英文别名: (2R,3R,4R,5S)-2-(hydroxymethyl)-1-[3-(3-propoxyphenyl)propyl]piperidine-3,4,5-triol
• CAS: 1383152-98-4
• 化学式: C₁₈H₂₉NO₅
• 分子量: 339.432
• InChiKey: RBVNMVUNDNYSBX-XMTFNYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(3-propoxyphenyl)-1-propanol 在 silica gel 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 (2R,3R,4R,5S)-2-(hydroxymethyl)-1-(3-(3-propoxyphenyl)propyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v

文献信息

• [EN] NON-LYSOSOMAL GLUCOSYLCERAMIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDASE NON LYSOSOMALE ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2021224865A1

  公开（公告）日：2021-11-11

  The invention provides compounds for inhibiting glucosylceramidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds.

  这项发明提供了用于抑制葡萄糖酰胺酶的化合物，这些化合物的前药以及包括这些化合物或化合物的前药的药物组合物。