[(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxy-hexyl] diethyl phosphate | 612493-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxy-hexyl] diethyl phosphate
• 英文别名: [(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxyhexyl] diethyl phosphate
• CAS: 612493-11-5
• 化学式: C₁₂H₂₆NO₉P
• 分子量: 359.313
• InChiKey: XUOLFRDQUIYYQU-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxy-hexyl] diethyl phosphate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以40%的产率得到[(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxy-hexyl] ethyl hydrogen phosphate
  参考文献：
  名称：

  Hydrophobic derivatives of 2-amino-2-deoxy-d-glucitol-6-phosphate: A new type of d-Glucosamine-6-phosphate synthase inhibitors with antifungal action

  摘要：

  Several N-acyl and ester derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) have been synthesised and tested as inhibitors of fungal enzymes involved in early steps of chitin biosynthesis and for antifungal activity. All the tested derivatives were found to be much poorer inhibitors of the enzyme, D-glucosamine-6-phosphate (GIcN-6-P) synthase, than the parent compound but some of them exhibited much better antifungal activity. MIC values for the investigated compounds ranged between 10 mg mL(-1), found for ADGP and 0.3 mg mL(-1) for the most active derivative, namely ADGP dimethyl ester. Increased affinity of ADGP derivatives to the artificial immobilised cell membrane was correlated with their enhanced ability to be taken up by fungal cells by free diffusion. It was found that some of the examined derivatives behaved as 'pro-drugs' and after internalisation were converted into ADGP in the cell-free extract. This conversion was relatively rapid for ADGP esters but very slow for N-acyl derivatives. Results of our studies demonstrate a possibility of design and preparation of GIcN-6-P synthase inhibitors exhibiting antifungal activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00049-x
• 作为产物：
  描述：

  D-GlcNAc 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 silver cyanide 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙醇 为溶剂， 反应 82.5h， 生成 [(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxy-hexyl] diethyl phosphate
  参考文献：
  名称：

  Hydrophobic derivatives of 2-amino-2-deoxy-d-glucitol-6-phosphate: A new type of d-Glucosamine-6-phosphate synthase inhibitors with antifungal action

  摘要：

  Several N-acyl and ester derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) have been synthesised and tested as inhibitors of fungal enzymes involved in early steps of chitin biosynthesis and for antifungal activity. All the tested derivatives were found to be much poorer inhibitors of the enzyme, D-glucosamine-6-phosphate (GIcN-6-P) synthase, than the parent compound but some of them exhibited much better antifungal activity. MIC values for the investigated compounds ranged between 10 mg mL(-1), found for ADGP and 0.3 mg mL(-1) for the most active derivative, namely ADGP dimethyl ester. Increased affinity of ADGP derivatives to the artificial immobilised cell membrane was correlated with their enhanced ability to be taken up by fungal cells by free diffusion. It was found that some of the examined derivatives behaved as 'pro-drugs' and after internalisation were converted into ADGP in the cell-free extract. This conversion was relatively rapid for ADGP esters but very slow for N-acyl derivatives. Results of our studies demonstrate a possibility of design and preparation of GIcN-6-P synthase inhibitors exhibiting antifungal activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00049-x