(3R,4r,5S)-1-octylpiperidine-3,4,5-triol | 1233944-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4r,5S)-1-octylpiperidine-3,4,5-triol
• 英文别名: (3R,5S)-1-octylpiperidine-3,4,5-triol；N-octyl-1,5-dideoxy-1,5-iminoxylitol
• CAS: 1233944-52-9；1314889-17-2
• 化学式: C₁₃H₂₇NO₃
• 分子量: 245.362
• InChiKey: PCHZTBUOIUSSAT-ITGUQSILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 在 硼烷四氢呋喃络合物 、 palladium 10% on activated carbon 、 氢气 、 sodium cyanoborohydride 、 臭氧 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 28.3h， 生成 (3R,4r,5S)-1-octylpiperidine-3,4,5-triol
  参考文献：
  名称：

  Synthetic N-Alkylated Iminosugars as New Potential Immunosuppressive Agents

  摘要：

  The new emerging immunosuppressive effects displayed by iminosugars have not been much investigated so far. Several new N-alkyl dideoxy iminoalditols were designed and synthesized to explore their immunosuppressive effects. These iminosugars inhibited the proliferation of mouse splenocytes and the secretion of both IFN-gamma and IL-4, which are the hallmark cytokines of Th1 and Th2 cells, respectively. Some compounds exerted good inhibitory effects. More importantly, the synthetic iminosugars prolonged the allograft survival in the mouse skin transplantation experiment. Our results provide a lead for further elucidation of the structure-activity relationships and modifications of iminosugars for better immunosuppressive agents.

  DOI：

  10.1021/ml2000998

文献信息

• [EN] GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GLYCOSIDASES ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2014032184A1

  公开（公告）日：2014-03-06

  The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  该发明提供了用于抑制糖苷酶的化合物，这些化合物的前药，以及包括这些化合物或这些化合物的前药的药物组合物。该发明还提供了用于治疗与O-GlcNAcase缺乏或过度表达、O-GlcNAc的积累或缺乏相关的疾病和障碍的方法。
• GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Alectos Therapeutics Inc.

  公开号：US20150299122A1

  公开（公告）日：2015-10-22

  The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  本发明提供了抑制糖苷酶的化合物，该化合物的前药，以及包括该化合物或该化合物的前药的制药组合物。本发明还提供了治疗与O-GlcNA酶的缺乏或过度表达、O-GlcNAc的积累或缺乏有关的疾病和障碍的方法。
• Rational Design and Synthesis of Highly Potent Pharmacological Chaperones for Treatment of N370S Mutant Gaucher Disease
  作者：Guan-Nan Wang、Gabriele Reinkensmeier、Si-Wei Zhang、Jian Zhou、Liang-Ren Zhang、Li-He Zhang、Terry D. Butters、Xin-Shan Ye

  DOI：10.1021/jm801506m

  日期：2009.5.28

  Highly potent N-substituted delta-lactams have been rationally designed and synthesized by a concise route with a one-pot tandem reaction as key step. These iminosugars show weak inhibition of wildtype beta-glucocerebrosidase but 3- to 6-fold increases in mutant enzyme activity (N370S).
• Synthetic N-Alkylated Iminosugars as New Potential Immunosuppressive Agents
  作者：Guan-Nan Wang、Yulan Xiong、Jia Ye、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/ml2000998

  日期：2011.9.8

  The new emerging immunosuppressive effects displayed by iminosugars have not been much investigated so far. Several new N-alkyl dideoxy iminoalditols were designed and synthesized to explore their immunosuppressive effects. These iminosugars inhibited the proliferation of mouse splenocytes and the secretion of both IFN-gamma and IL-4, which are the hallmark cytokines of Th1 and Th2 cells, respectively. Some compounds exerted good inhibitory effects. More importantly, the synthetic iminosugars prolonged the allograft survival in the mouse skin transplantation experiment. Our results provide a lead for further elucidation of the structure-activity relationships and modifications of iminosugars for better immunosuppressive agents.