3-O-(2-acetamido-2-deoxy-6-O-sulfo-α-D-glucopyranosyl)-2,6-dideoxy-2,6-imino-L-gulonic acid sodium salt

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-O-(2-acetamido-2-deoxy-6-O-sulfo-α-D-glucopyranosyl)-2,6-dideoxy-2,6-imino-L-gulonic acid sodium salt
• 英文别名: sodium;[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3R,4R,5S)-2-carboxy-4,5-dihydroxypiperidin-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methyl sulfate
• 化学式: C₁₄H₂₃N₂O₁₃S*Na
• 分子量: 482.398
• InChiKey: UQROTFOAWWCCQH-SIXIVWLUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -8.42
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  253
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 palladium on activated charcoal jones reagent 、 三甲基氨基磺酸 、 氢气 、 caesium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 68.17h， 生成 3-O-(2-acetamido-2-deoxy-6-O-sulfo-α-D-glucopyranosyl)-2,6-dideoxy-2,6-imino-L-gulonic acid sodium salt
  参考文献：
  名称：

  Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure

  摘要：

  Aza-analogue of the basic disaccharide unit of heparane sulfate was designed as a potent inhibitor against heparanase produced by solid tumors cell, and synthesized via a coupling reaction of phenyl 2-azide-1-thio-D-glucopyranoside derivatives with a partially protected 1-deoxynojirimycin derived from D-glucose. The azapseudodisaccharide inhibited tumor cell heparanase with IC50 value of 58-63 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00642-1

文献信息

• Synthesis of a Potential Heparanase Inhibitor
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1246/cl.1994.2119

  日期：1994.11

  Aza-analog of the basic disaccharide unit in heparan sulfate was designed as a potential inhibitor against heparanase produced by solid tumor cells, and synthesized via a coupling reaction of a phenyl 2-azido-1-thio-d-glucopyranoside derivative with a partially protected 1-deoxynojirymycin derived from d-glucose, followed by manipulation such as imino acid formation, O-sulfation.

  基于肝素硫酸盐中基本二糖单元设计了一种氮杂类似物，作为针对实体瘤细胞产生的肝素酶的潜在抑制剂，并通过苯基2-叠氮基-1-硫代-D-吡�糖苷衍生物与部分保护的1-脱氧野尻霉素（来自D-葡萄糖）的偶联反应合成，随后进行亚胺酸形成、O-硫酸化等操作。
• Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara、Motowo Nakajima

  DOI：10.1016/s0040-4020(01)00642-1

  日期：2001.8

  Aza-analogue of the basic disaccharide unit of heparane sulfate was designed as a potent inhibitor against heparanase produced by solid tumors cell, and synthesized via a coupling reaction of phenyl 2-azide-1-thio-D-glucopyranoside derivatives with a partially protected 1-deoxynojirimycin derived from D-glucose. The azapseudodisaccharide inhibited tumor cell heparanase with IC50 value of 58-63 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.