2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-6-(5''-azido-1'',5''-dideoxy-β-D-ribos-1''-yl)-D-glucitol | 1022954-66-0

• 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)-6-(5''-azido-1'',5''-dideoxy-β-D-ribos-1''-yl)-D-glucitol
• 英文别名: 1-[[(2S,3R,4R,5R)-5-[[(2R,3R,4S,5R)-5-(azidomethyl)-3,4-dihydroxyoxolan-2-yl]oxymethyl]-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl]pyrimidine-2,4-dione
• CAS: 1022954-66-0
• 化学式: C₂₉H₃₃N₅O₉
• 分子量: 595.609
• InChiKey: NYNXBNJLYUGQNN-PNDOSKJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-6-(5''-azido-1'',5''-dideoxy-β-D-ribos-1''-yl)-D-glucitol 在 氢气 、 钯 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以20%的产率得到2,5-anhydro-1-deoxy-1-(uracil-1'-yl)-6-(5''-amino-1'',5''-dideoxy-β-D-ribos-1''-yl)-D-glucitol
  参考文献：
  名称：

  Bacterial transferase MraY inhibitors: Synthesis and biological evaluation

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.04.023
• 作为产物：
  描述：

  2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-6-(5''-azido-1'',5''-dideoxy-2'',3''-O-isopentylidene-β-D-ribos-1''-yl)-D-glucitol 在 三氟乙酸 作用下， 以 水 为溶剂， 以80%的产率得到2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-(uracil-1'-yl)-6-(5''-azido-1'',5''-dideoxy-β-D-ribos-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