sodium 7-O-(2-deoxy-2-sulfamido-α-D-glucopyranosyl)-4-methylcoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: sodium 7-O-(2-deoxy-2-sulfamido-α-D-glucopyranosyl)-4-methylcoumarin
• 英文别名: 4-Methylumbelliferyl 2-Sulfamino-2-deoxy-alpha-D-glucopyranoside Sodium Salt；sodium;N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]sulfamate
• 化学式: C₁₆H₁₈NO₁₀S*Na
• 分子量: 439.375
• InChiKey: LMECUNAMBHBGFU-MYDYNYEJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.66
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯 在 benzamine 、 三氟化硼乙醚 、 sodium methylate 、 三氧化硫吡啶 、 苯硫酚 、 三乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 sodium 7-O-(2-deoxy-2-sulfamido-α-D-glucopyranosyl)-4-methylcoumarin
  参考文献：
  名称：

  Synthesis of 7-O-(2-deoxy-2-sulfamido-α-d-glucopyranosyl)-4-methylcoumarin sodium salt: a fluorogenic substrate for sulfamidase

  摘要：

  The title compound, useful for testing the efficacy of heparin sulfamidase, was synthesized in good yield starting from 2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl fluoride, reducing the azido group efficiently with SnCl2-PhSH-Et3N reagent and finally crystallizing the N-sulfated product from methanol after deacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00088-5

文献信息

• [EN] TARGETED HEPARAN SULFATASE COMPOUNDS<br/>[FR] COMPOSÉS D'HÉPARANE SULFATASE CIBLÉS
  申请人：ANGIOCHEM INC

  公开号：WO2014194428A1

  公开（公告）日：2014-12-11

  The present invention is related to a compound that includes a lysosomal enzyme (e.g., heparan sulfatase) and a targeting moiety, for example, where compound is a fusion protein including heparan sulfatase and Angiopep-2. In certain embodiments, these compounds, owning to the presence of the targeting moiety can crossing the blood-brain barrier or accumulate in the lysosome more effectively than the enzyme alone. The invention also features methods for treating lysosomal storage disorders (e.g., mucopolysaccharidosis Type IlIa) using such compounds.