1,3,4,6-tetra-O-acetyl-2-N-(4-methoxy)benzoyl-2-deoxy-β-D-glucopyranose | 113951-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-N-(4-methoxy)benzoyl-2-deoxy-β-D-glucopyranose
• 英文别名: N-Anisoyl-1,3,4,6-tetra-O-acetyl-β-D-glucosamin
• CAS: 113951-09-0
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: NHGYCXONZZAFHK-CDVBAKLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-N-(4-methoxy)benzoyl-2-deoxy-β-D-glucopyranose 在 劳森试剂 、 甲醇 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 1,2-dideoxy-2'-(4-methoxy)phenyl-α-D-glucopyrano-[2,1-d]-Δ2'-thiazoline
  参考文献：
  名称：

  Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases

  摘要：

  beta-N-Acetyl-D-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using D-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two beta-N-acetyl-D-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 beta-N-acetyl-D-hexosaminidase. Among the compounds tested, compounds 5a (IC50 = 12.6 mu M, hOGA) and 5e (IC50 = 12.5 mu M, OfOGA) proved to be a highly selective and potent inhibitor. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.06.004
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 1,3,4,6-tetra-O-acetyl-2-N-(4-methoxy)benzoyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases

  摘要：

  beta-N-Acetyl-D-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using D-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two beta-N-acetyl-D-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 beta-N-acetyl-D-hexosaminidase. Among the compounds tested, compounds 5a (IC50 = 12.6 mu M, hOGA) and 5e (IC50 = 12.5 mu M, OfOGA) proved to be a highly selective and potent inhibitor. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.06.004