p-methoxyphenyl 4,6-dideoxy-4,6-diazido-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside | 620172-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 4,6-dideoxy-4,6-diazido-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: p-methylphenyl-4,6-dideoxy-4,6-diazido-2,3-O-benzoyl-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3-azido-2-(azidomethyl)-5-benzoyloxy-6-(4-methylphenyl)sulfanyloxan-4-yl] benzoate
• CAS: 620172-02-3
• 化学式: C₂₇H₂₄N₆O₅S
• 分子量: 544.591
• InChiKey: JHBVCUQEYWGKBN-CXBVJKJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4,6-dideoxy-4,6-diazido-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside 、 acetic acid 2-[3-acetoxy-4-(4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-5-hydroxymethyl-tetrahydro-furan-2-yloxy]-4,6-diazido-3-(4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  A New Class of Branched Aminoglycosides:  Pseudo-Pentasaccharide Derivatives of Neomycin B

  摘要：

  The clinically important antibiotic neomycin B was modified at position C5" by adding one extra sugar ring in the beta-configuration, and the observed pseudo-pentasaccharides were tested against various bacterial strains, including pathogenic and resistant strains. The designed antibiotics show antibacterial activity superior to that of neomycin B against pathogenic and resistant bacterial strains.

  DOI：

  10.1021/ol035213i
• 作为产物：
  描述：

  p-methoxyphenyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside 在 吡啶 、 三氟甲磺酸酐 、 六甲基磷酰三胺 、 sodium azide 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 3.42h， 以72%的产率得到p-methoxyphenyl 4,6-dideoxy-4,6-diazido-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes

  摘要：

  一种新型氨基糖苷类药物，与目前已有的氨基糖苷类药物在骨架方面具有一些结构特征，同时又具有显著的结构差异。这种相似性使得这些氨基糖苷类药物具有很高的抗菌作用和有效性，而显著的差异使得这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的发展。

  公开号：

  US20050004052A1

文献信息

• Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes
  申请人：Baasov Timor

  公开号：US20050004052A1

  公开（公告）日：2005-01-06

  A novel group of aminoglycosides which share some structural features of currently available aminoglycosides with regard to the backbone, while also having significant structural differences. The similarity enables these aminoglycosides to be highly potent and effective antibiotics, while the significant differences enable these aminoglycosides to reduce or even block antibiotic resistance.

  一种新型氨基糖苷类药物，与目前已有的氨基糖苷类药物在骨架方面具有一些结构特征，同时又具有显著的结构差异。这种相似性使得这些氨基糖苷类药物具有很高的抗菌作用和有效性，而显著的差异使得这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的发展。
• A New Class of Branched Aminoglycosides:  Pseudo-Pentasaccharide Derivatives of Neomycin B
  作者：Micha Fridman、Valery Belakhov、Sima Yaron、Timor Baasov

  DOI：10.1021/ol035213i

  日期：2003.10.1

  The clinically important antibiotic neomycin B was modified at position C5" by adding one extra sugar ring in the beta-configuration, and the observed pseudo-pentasaccharides were tested against various bacterial strains, including pathogenic and resistant strains. The designed antibiotics show antibacterial activity superior to that of neomycin B against pathogenic and resistant bacterial strains.