ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside | 1334525-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside
• CAS: 1334525-91-5
• 化学式: C₁₅H₁₉N₃O₄S
• 分子量: 337.4
• InChiKey: XFWUPFSGOVDQSD-KYFQHEKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside 在 二乙胺基三氟化硫 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU

  摘要：

  GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D-glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-alpha-D-glucopyranoside 6-phosphate (1 alpha), methyl 2-amino-2deoxyl-beta-D-glucopyranoside 6-phosphate (1 beta), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-alpha-D-glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-alpha-Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1 alpha, 1 beta, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1 beta, 1 beta and 2 were inactive against GlmM and GlmU even at high concentrations. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.024
• 作为产物：
  描述：

  ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 六甲基磷酰三胺 、 15-冠醚-5 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside
  参考文献：
  名称：

  Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU

  摘要：

  GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D-glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-alpha-D-glucopyranoside 6-phosphate (1 alpha), methyl 2-amino-2deoxyl-beta-D-glucopyranoside 6-phosphate (1 beta), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-alpha-D-glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-alpha-Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1 alpha, 1 beta, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1 beta, 1 beta and 2 were inactive against GlmM and GlmU even at high concentrations. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.024