[(2R,3S,4R,5S)-5-(3-carbamoyl-4-phenoxyphenyl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate | 949587-40-0

• 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-(3-carbamoyl-4-phenoxyphenyl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 949587-40-0
• 化学式: C₁₈H₂₀NO₉P
• 分子量: 425.332
• InChiKey: IUCIUGXOUIDNQA-VQHPVUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  169
• 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-(3-carbamoyl-4-phenoxyphenyl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate 、 5'-腺嘌呤核苷酸 生成 4-phenoxyBAD
  参考文献：
  名称：

  Synthesis of 4-phenoxybenzamide adenine dinucleotide as NAD analogue with inhibitory activity against enoyl-ACP reductase (InhA) of Mycobacterium tuberculosis

  摘要：

  The chemical synthesis of 4-phenoxybenzamide adenine dinucleotide (3), a NAD analogue which mimics isoniazid-NAD adduct and inhibits Mycobacterium tuberculosis NAD-dependent enoyl-ACP reductase (InhA), is reported. The 4-phenoxy benzamide riboside (1) has been prepared as a key intermediate, converted into its 5 '-mononucleotide (2), and coupled with AMP imidazolide to give the desired NAD analogue 3. It inhibits InhA with IC50 = 27 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.084
• 作为产物：
  描述：

  2-氟-5-碘苯甲腈 在 potassium trimethylsilonate 、 异丙基氯化镁 、 三溴化硼 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(2R,3S,4R,5S)-5-(3-carbamoyl-4-phenoxyphenyl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  Synthesis of 4-phenoxybenzamide adenine dinucleotide as NAD analogue with inhibitory activity against enoyl-ACP reductase (InhA) of Mycobacterium tuberculosis

  摘要：

  The chemical synthesis of 4-phenoxybenzamide adenine dinucleotide (3), a NAD analogue which mimics isoniazid-NAD adduct and inhibits Mycobacterium tuberculosis NAD-dependent enoyl-ACP reductase (InhA), is reported. The 4-phenoxy benzamide riboside (1) has been prepared as a key intermediate, converted into its 5 '-mononucleotide (2), and coupled with AMP imidazolide to give the desired NAD analogue 3. It inhibits InhA with IC50 = 27 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.084