N-((3S,4R,5R,6R)-4,5-dihydroxy-6-methylpiperidin-3-yl)acetamide | 134735-50-5

• 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: N-((3S,4R,5R,6R)-4,5-dihydroxy-6-methylpiperidin-3-yl)acetamide
• 英文别名: N-[(3S,4R,5R,6R)-4,5-dihydroxy-6-methylpiperidin-3-yl]acetamide
• CAS: 134735-50-5
• 化学式: C₈H₁₆N₂O₃
• 分子量: 188.227
• InChiKey: BUHKKYXYOVYMPN-PXBUCIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-N-acetyl-2-(diethoxymethyl)aziridine 在 sodium azide 、 zinc(II) chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-((3S,4R,5R,6R)-4,5-dihydroxy-6-methylpiperidin-3-yl)acetamide
  参考文献：
  名称：

  Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitors

  摘要：

  A combined fructose 1,6-diphosphate aldolase reaction and catalytic reductive amination has been used in the asymmetric synthesis of azasugars structurally corresponding to N-acetylglucosamine, N-acetylmannosamine, and deoxyhexoses. The 6-deoxyazasugars were prepared by direct hydrogenolysis of the aldolase product without removal of the 6-phosphate group. Both (R)- and (S)-3-azido-2-acetamidopropanal used as substrates in the aldolase reactions were prepared from the corresponding lipase-resolved 2-hydroxy species followed by formation of an aziridine intermediate and opening of the aziridine with azide. Evaluation of these azasugars and their diastereomerically pure tertiary amine oxides as well as 5-thioglucose and its sulfoxide derivatives as glycosidase inhibitors was carried out. It was found that all synthetic azasugars and 5-thioglucose were strong inhibitors, but oxidation of the ring heteroatom weakened the inhibition. With the aid of molecular modeling and inhibition analysis, a structure-K(i) relation of inhibitors was established which provides useful information for the design of new glycosidase inhibitors.

  DOI：

  10.1021/ja00016a039

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：WO2014032187A1

  公开（公告）日：2014-03-06

  The invention provides compounds of Formula (I) for inhibiting gh cosidases, prodrugs of the compounds, and pharmaceutical compositions comprising the compounds or prodrugs of the compounds. The invention also provides method of treating diseases and disorders related to deficiency or over-expression of O-gh coprotein 2-acetamido-2- deoxy-β-D-giucopyranosidase (O-GlcNAcase), accumulation or deficiency of 2-acetamido-2-deoxy-β-D- glucopyranoside (O-GlcNAc).

  该发明提供了化合物(I)的配方，用于抑制ghcosidase，该化合物的前药以及包含该化合物或该化合物的前药的制药组合物。该发明还提供了治疗与O-ghcoprotein 2-乙酰氨基-2-脱氧-β-D-葡萄糖苷酶（O-GlcNAcase）的缺乏或过度表达，2-乙酰氨基-2-脱氧-β-D-葡萄糖苷醇（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：US20150218097A1

  公开（公告）日：2015-08-06

  The invention provides compounds of Formula (I) for inhibiting gh cosidases, prodrugs of the compounds, and pharmaceutical compositions comprising the compounds or prodrugs of the compounds. The invention also provides method of treating diseases and disorders related to deficiency or over-expression of O-gh coprotein 2-acetamido-2-deoxy-β-D-glucopyranosidase (O-GlcNAcase), accumulation or deficiency of 2-acetamido-2-deoxy-β-D-glucopyranoside (O-GlcNAc).

  本发明提供了化合物(I)的抑制gh cosidases的作用，该化合物的前药以及包含该化合物或该化合物的前药的药物组合物。本发明还提供了治疗与O-gh蛋白2-乙酰胺基-2-脱氧-β-D-葡萄糖吡喃酶(O-GlcNAcase)缺乏或过度表达、2-乙酰胺基-2-脱氧-β-D-葡萄糖吡喃苷(O-GlcNAc)积累或缺乏相关疾病和障碍的方法。
• C-REL INHIBITORS AND USES THEREOF
  申请人：CORNELL UNIVERSITY

  公开号：US20150218109A1

  公开（公告）日：2015-08-06

  Compounds having a c-Rel inhibiting property according to the formula: (1) wherein R 1 and R 2 are each independently selected from hydrogen atom and hydrocarbon groups having at least one and up to thirty carbon atoms and optionally substituted with one or more heteroatoms selected from halogen, nitrogen, oxygen, and sulfur; R 3 is selected from hydrocarbon groups having at least one and up to thirty carbon atoms and optionally substituted with one or more heteroatoms selected from halogen, nitrogen, oxygen, and sulfur; and X 1 , X 2 , and X 3 are each independently selected from oxygen and sulfur atoms. Methods for treating diseases and conditions associated with c-Rel overexpression by administering compounds of Formula (1) or a pharmaceutical composition thereof to a subject afflicted with such a disease or condition are also described.

  具有抑制c-Rel性质的化合物按照公式（1）：其中R1和R2各自独立地选择氢原子和至少一个碳原子至三十个碳原子的含有一个或多个杂原子（选自卤素、氮、氧和硫）的烃基，并且可以被一个或多个杂原子（选自卤素、氮、氧和硫）取代；R3选择至少一个碳原子至三十个碳原子的含有一个或多个杂原子（选自卤素、氮、氧和硫）的烃基，并且可以被一个或多个杂原子（选自卤素、氮、氧和硫）取代；X1、X2和X3各自独立地选择氧原子和硫原子。还描述了通过向患有这种疾病或情况的受试者投与公式（1）的化合物或其制剂来治疗与c-Rel过度表达相关的疾病和情况的方法。
• EP0576592A4
  申请人：——

  公开号：EP0576592A4

  公开（公告）日：1996-01-24
• OLIGOSACCHARIDE ENZYME SUBSTRATES AND INHIBITORS: METHODS AND COMPOSITIONS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP0576592B1

  公开（公告）日：2000-05-31