2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-D-glucitol | 1022954-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-D-glucitol
• 英文别名: 1-[[(2S,3R,4R,5R)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrimidine-2,4-dione
• CAS: 1022954-52-4
• 化学式: C₂₄H₂₆N₂O₆
• 分子量: 438.48
• InChiKey: DWUFPICUZHPBRY-KKSHJYNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl fluoride 、 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-D-glucitol 在 molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Efficient synthesis of a bacterial translocase MraY inhibitor

  摘要：

  The bacterial translocase MraY has recently been demonstrated as a prime target for the development of new antibiotics. We describe a straightforward synthesis of a new inhibitor I of this enzyme. The two key steps involve a tandem nucleophilic epoxide ring opening of C2-symmetrical bis-epoxide and subsequent O-heterocyclisation, followed by O-glycosylation. The in vitro biological evaluation of 1 at 2 mM showed an 81% of inhibition of the MraY activity. Therefore, congeners of I should permit detailed SAR investigations for the discovery of novel antibacterials. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.037
• 作为产物：
  描述：

  尿嘧啶 、 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 在 N,O-双(三甲基硅烷基)三氟乙酰胺 、 magnesium(II) perchlorate 作用下， 以 乙腈 为溶剂， 以46%的产率得到2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-D-glucitol
  参考文献：
  名称：

  Efficient synthesis of a bacterial translocase MraY inhibitor

  摘要：

  The bacterial translocase MraY has recently been demonstrated as a prime target for the development of new antibiotics. We describe a straightforward synthesis of a new inhibitor I of this enzyme. The two key steps involve a tandem nucleophilic epoxide ring opening of C2-symmetrical bis-epoxide and subsequent O-heterocyclisation, followed by O-glycosylation. The in vitro biological evaluation of 1 at 2 mM showed an 81% of inhibition of the MraY activity. Therefore, congeners of I should permit detailed SAR investigations for the discovery of novel antibacterials. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.037

文献信息

• Bacterial transferase MraY inhibitors: Synthesis and biological evaluation
  作者：Delphine Lecerclé、Anthony Clouet、Bayan Al-Dabbagh、Muriel Crouvoisier、Ahmed Bouhss、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1016/j.bmc.2010.04.023

  日期：2010.6.15

  New inhibitors of the bacterial transferase MraY are described. Their structure is based on an aminoribosyl-O-uridine like scaffold, readily obtained in two key steps. The amino group can be coupled with proline or guanylated. Alternatively, these amino, prolinyl or guanidinyl groups can be introduced through a triazole linker. Biological evaluation of these compounds on MraY from Bacillus subtilis revealed interesting inhibitory activity for both amino compounds. (C) 2010 Published by Elsevier Ltd.
• Efficient synthesis of a bacterial translocase MraY inhibitor
  作者：Anthony Clouet、Christine Gravier-Pelletier、Bayan Al-Dabbag、Ahmed Bouhss、Yves Le Merrer

  DOI：10.1016/j.tetasy.2008.01.037

  日期：2008.3

  The bacterial translocase MraY has recently been demonstrated as a prime target for the development of new antibiotics. We describe a straightforward synthesis of a new inhibitor I of this enzyme. The two key steps involve a tandem nucleophilic epoxide ring opening of C2-symmetrical bis-epoxide and subsequent O-heterocyclisation, followed by O-glycosylation. The in vitro biological evaluation of 1 at 2 mM showed an 81% of inhibition of the MraY activity. Therefore, congeners of I should permit detailed SAR investigations for the discovery of novel antibacterials. (C) 2008 Elsevier Ltd. All rights reserved.