1,4-dihydroxy-2-((3,4,6-tri-O-acetyl-2-deoxy-2-((trifluoroacetyl)amino)-β-D-glucosyloxy)methyl)-9,10-dihydro-9,10-anthracenedione | 102830-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-dihydroxy-2-((3,4,6-tri-O-acetyl-2-deoxy-2-((trifluoroacetyl)amino)-β-D-glucosyloxy)methyl)-9,10-dihydro-9,10-anthracenedione
• 英文别名: 1,4-dihydroxy-2-<<3,4,6-tri-O-acetyl-2-deoxy-2-<(trifluoroacetyl)amino>-β-D-glucosyloxy>methyl>-9,10-dihydro-9,10-anthracenedione；1,4-dihydroxy-2-({3,4,6-tri-O-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]-β-D-glucosyloxy}methyl)-9,10-dihydro-9,10-anthracenedione
• CAS: 102830-95-5
• 化学式: C₂₉H₂₆F₃NO₁₃
• 分子量: 653.52
• InChiKey: XWYWOSVXUKPSHD-RWCFXCBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  201.06
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1,4-dihydroxy-2-((3,4,6-tri-O-acetyl-2-deoxy-2-((trifluoroacetyl)amino)-β-D-glucosyloxy)methyl)-9,10-dihydro-9,10-anthracenedione 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以62%的产率得到1,4-dihydroxy-2-<(2-deoxy-2-amino-β-D-glucosyloxy)methyl>-9,10-dihydro-9,10-anthracenedione
  参考文献：
  名称：

  Synthesis of anthraquinonyl glucosaminosides and studies on the influence of aglycone hydroxyl substitution on superoxide generation, DNA binding, and antimicrobial properties

  摘要：

  A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (11a-e) with bromo sugar 12 followed by saponification. These glycosides were intended to serve as models to study the role played by the hydroxyl substituents on the aglycone portion of the antitumor anthracycline antibiotics. Superoxide generation as measured in rat heart sarcosomes was found to increase with the addition of successive hydroxyl groups to the anthraquinone nucleus. The 1,8-dihydroxy pattern was determined to generate significantly less superoxide than the 1,4-dihydroxy pattern. Hydroxyl substitution was also observed to stabilize the complex formed between the anthraquinones and DNA and was required for antibacterial activity against a number of Gram-positive organisms.

  DOI：

  10.1021/jm00159a024
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide 、 digiferrol 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以21%的产率得到1,4-dihydroxy-2-((3,4,6-tri-O-acetyl-2-deoxy-2-((trifluoroacetyl)amino)-β-D-glucosyloxy)methyl)-9,10-dihydro-9,10-anthracenedione
  参考文献：
  名称：

  Synthesis of anthraquinonyl glucosaminosides and studies on the influence of aglycone hydroxyl substitution on superoxide generation, DNA binding, and antimicrobial properties

  摘要：

  A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (11a-e) with bromo sugar 12 followed by saponification. These glycosides were intended to serve as models to study the role played by the hydroxyl substituents on the aglycone portion of the antitumor anthracycline antibiotics. Superoxide generation as measured in rat heart sarcosomes was found to increase with the addition of successive hydroxyl groups to the anthraquinone nucleus. The 1,8-dihydroxy pattern was determined to generate significantly less superoxide than the 1,4-dihydroxy pattern. Hydroxyl substitution was also observed to stabilize the complex formed between the anthraquinones and DNA and was required for antibacterial activity against a number of Gram-positive organisms.

  DOI：

  10.1021/jm00159a024