N-[7-amino-hept-1-yl]-2-acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol | 1220907-09-4

• 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-[7-amino-hept-1-yl]-2-acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol
• 英文别名: N-[(3S,4R,5R,6R)-1-(7-aminoheptyl)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide
• CAS: 1220907-09-4
• 化学式: C₁₅H₃₁N₃O₄
• 分子量: 317.429
• InChiKey: QWZPVJYIJZQINK-GBJTYRQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[7-amino-hept-1-yl]-2-acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol 在 copper(ll) sulfate pentahydrate 、 triflic azide 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以83%的产率得到C₁₅H₂₉N₅O₄
  参考文献：
  名称：

  1,5-Dideoxy-1,5-imino-D-glucitol Compounds

  摘要：

  规范中显示的1,5-二去氧-1,5-亚胺-D-葡萄糖醇化合物。还公开了一种治疗己糖氨基酸酶相关疾病的方法。

  公开号：

  US20100113519A1

文献信息

• Development of GlcNAc-Inspired Iminocyclitiols as Potent and Selective <i>N</i>-Acetyl-β-Hexosaminidase Inhibitors
  作者：Ching-Wen Ho、Shinde D. Popat、Ta-Wei Liu、Keng-Chang Tsai、Meng-Jung Ho、Wei-Hung Chen、An-Suei Yang、Chun-Hung Lin

  DOI：10.1021/cb100011u

  日期：2010.5.21

  Human N-acetyl-beta-hexosaminidase (Hex) isozymes are considered to be important targets for drug discovery. They are directly linked to osteoarthritis because Hex is the predominant glycosidase released by chondrocytes to degrade glycosaminoglycan. Hex is also associated with lysosomal storage disorders. We report the discovery of GlcNAc-type iminocyclitiols as potent and selective Hex inhibitors, likely contributed by the gain of extra electrostatic and hydrophobic interactions. The most potent inhibitor had a K-i of 0.69 nM against human Hex B and was 2.5 x 10(5) times more selective for Hex B than for a similar human enzyme O-GlcNAcase. These glycosidase inhibitors were shown to modulate intracellular levels of glycolipids, including ganglioside-GM2 and asialoganglioside-GM2.
• 1,5-Dideoxy-1,5-imino-D-glucitol Compounds
  申请人：Lin Chun-Hung

  公开号：US20100113519A1

  公开（公告）日：2010-05-06

  1,5-Dideoxy-1,5-imino-D-glucitol compounds as shown in the specification. Also disclosed is a method of treating a hexosaminidase-associated disease.

  规范中显示的1,5-二去氧-1,5-亚胺-D-葡萄糖醇化合物。还公开了一种治疗己糖氨基酸酶相关疾病的方法。