2-(N-benzyloxycarbonylamino)-2-deoxy-D-glucose-6-phosphate dimethyl ester | 612493-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(N-benzyloxycarbonylamino)-2-deoxy-D-glucose-6-phosphate dimethyl ester
• CAS: 612493-13-7
• 化学式: C₁₆H₂₄NO₁₀P
• 分子量: 421.341
• InChiKey: DYBRWQXVWAFUFF-GBJTYRQASA-N

反应信息

• 作为反应物：
  描述：

  2-(N-benzyloxycarbonylamino)-2-deoxy-D-glucose-6-phosphate dimethyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 Phosphoric acid (2R,3S,4R,5S)-5-amino-2,3,4,6-tetrahydroxy-hexyl ester dimethyl ester
  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：

  重氮甲烷 、 2-(N-benzyloxycarbonylamino)-2-deoxy-D-glucose-6-phosphate 以 乙醚 、 水 为溶剂， 以90 mg的产率得到2-(N-benzyloxycarbonylamino)-2-deoxy-D-glucose-6-phosphate dimethyl ester
  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