acetyl 4,6-diazido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranoside | 485809-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetyl 4,6-diazido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranoside
• 英文别名: 1,2,3-tri-O-acetyl-4,6-deoxy-4,6-di-azido-D-glucopyranoside；(2R,3R,4S,5R,6R)-5-Azido-6-(azidomethyl)tetrahydro-2H-pyran-2,3,4-triyl triacetate；[(2R,3R,4S,5R,6R)-2,3-diacetyloxy-5-azido-6-(azidomethyl)oxan-4-yl] acetate
• CAS: 485809-75-4
• 化学式: C₁₂H₁₆N₆O₇
• 分子量: 356.295
• InChiKey: NXFBOSDFKNUIMG-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  acetyl 4,6-diazido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranoside 在 4 A molecular sieve 、 乙酸肼 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2S,3R,4S,5S,6R)-5-Azido-6-azidomethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042
• 作为产物：
  描述：

  methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 草酰氯 、 三氟甲磺酸酐 、 硫酸 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 acetyl 4,6-diazido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• The Identification of Perillyl Alcohol Glycosides with Improved Antiproliferative Activity
  作者：Nitin S. Nandurkar、Jianjun Zhang、Qing Ye、Larissa V. Ponomareva、Qing-Bai She、Jon S. Thorson

  DOI：10.1021/jm500870u

  日期：2014.9.11

  A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribosomal protein phosphorylation as a putative mechanism of representative POH glycosides. The most active glycoside from this cumulative study (4'-azido-d-glucoside, PG9) represents one of the most cytotoxic POH analogues reported to date.