3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5,6,7-tetrahydro-8H-imidazo[4,5-d][1,3]diazepine-5,8-dione | 139173-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5,6,7-tetrahydro-8H-imidazo[4,5-d][1,3]diazepine-5,8-dione
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(5,8-dioxo-6,7-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)oxolan-2-yl]methyl benzoate
• CAS: 139173-35-6
• 化学式: C₃₂H₂₆N₄O₉
• 分子量: 610.58
• InChiKey: QTYLKKKDFSQPGC-GTVIQNQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5,6,7-tetrahydro-8H-imidazo[4,5-d][1,3]diazepine-5,8-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以69%的产率得到3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3,4,6,7-tetrahydro-imidazo[4,5-d][1,3]diazepine-5,8-dione
  参考文献：
  名称：

  Irreversible, Tight-Binding Inhibition of Adenosine Deaminase by Coformycins: Inhibitor Structural Features That Contribute to the Mode of Enzyme Inhibition

  摘要：

  Coformycin analogues 1-6 were synthesized and biochemically screened against adenosine deaminase in order to assess the relative contributions of N-4, N-6, and the N-3 sugar moiety to the mane of enzyme inhibition. Our results indicate that N-4 plays a relatively greater role than N-6 in enzyme tight-binding, and that a benzyl group can substitute for the sugar moiety at N-3. The absence of a sugar or benzyl group at N-3, however, leads to lass of activity. The hydroxyl group at C-8, while crucial for activity, does not alone confer the tight-binding characteristics to coformycins.

  DOI：

  10.1080/07328319708006131
• 作为产物：
  描述：

  3-benzyl-4,5,6,7-tetrahydro-8H-imidazo[4,5-d][1,3]diazepine-5,8-dione 在 palladium dihydroxide 三甲基氯硅烷 、 三氟甲磺酸 、 氢气 、 六甲基二硅氮烷 作用下， 以 溶剂黄146 为溶剂， 生成 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5,6,7-tetrahydro-8H-imidazo[4,5-d][1,3]diazepine-5,8-dione
  参考文献：
  名称：

  Irreversible, Tight-Binding Inhibition of Adenosine Deaminase by Coformycins: Inhibitor Structural Features That Contribute to the Mode of Enzyme Inhibition

  摘要：

  Coformycin analogues 1-6 were synthesized and biochemically screened against adenosine deaminase in order to assess the relative contributions of N-4, N-6, and the N-3 sugar moiety to the mane of enzyme inhibition. Our results indicate that N-4 plays a relatively greater role than N-6 in enzyme tight-binding, and that a benzyl group can substitute for the sugar moiety at N-3. The absence of a sugar or benzyl group at N-3, however, leads to lass of activity. The hydroxyl group at C-8, while crucial for activity, does not alone confer the tight-binding characteristics to coformycins.

  DOI：

  10.1080/07328319708006131

文献信息

• Ring expanded nucleosides and nucleotides
  申请人：——

  公开号：US20040077564A1

  公开（公告）日：2004-04-22

  The present invention relates to compositions comprising analogues of purine nucleosides containing a ring-expanded (“fat”) heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such compositions, as well as methods of use thereof. In particular, these compositions may be utilized in the treatment of certain cancers, bacterial, fungal, parasitic, and viral infections, including, but not limited to, Acquired Immunodeficiency Syndrome (AIDS), hepatitis, Epstein-Barr and cytomegalovirus.

  本发明涉及含有环扩张（“肥胖”）杂环环代替嘌呤的嘌呤核苷类似物和未经改性或改性的糖残基的组合物，以及这些组合物的药学上可接受的衍生物，以及其使用方法。特别地，这些组合物可用于治疗某些癌症、细菌、真菌、寄生虫和病毒感染，包括但不限于获得性免疫缺陷综合症（AIDS）、肝炎、EB病毒和巨细胞病毒。
• Ring-expanded nucleosides and nucleotides
  申请人：Nabi

  公开号：EP1227103B1

  公开（公告）日：2006-07-26
• RING-EXPANDED NUCLEOSIDES AND NUCLEOTIDES
  申请人：Nabi

  公开号：EP0724587B1

  公开（公告）日：2002-09-04
• US6677310B1
  申请人：——

  公开号：US6677310B1

  公开（公告）日：2004-01-13
• Irreversible, Tight-Binding Inhibition of Adenosine Deaminase by Coformycins: Inhibitor Structural Features That Contribute to the Mode of Enzyme Inhibition
  作者：Mikyung Hong、Ramachandra S. Hosmane

  DOI：10.1080/07328319708006131

  日期：1997.7

  Coformycin analogues 1-6 were synthesized and biochemically screened against adenosine deaminase in order to assess the relative contributions of N-4, N-6, and the N-3 sugar moiety to the mane of enzyme inhibition. Our results indicate that N-4 plays a relatively greater role than N-6 in enzyme tight-binding, and that a benzyl group can substitute for the sugar moiety at N-3. The absence of a sugar or benzyl group at N-3, however, leads to lass of activity. The hydroxyl group at C-8, while crucial for activity, does not alone confer the tight-binding characteristics to coformycins.