1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole | 94619-73-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole
• 英文别名: 4,5-dicyano-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole；1-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-4,5-dicyanoimidazole；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4,5-dicyanoimidazol-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 94619-73-5
• 化学式: C₃₁H₂₂N₄O₇
• 分子量: 562.538
• InChiKey: MMUAYKUUUPKUSQ-BIYDSLDMSA-N

物化性质

• 沸点：
  808.5±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole 在 sodium hydroxide 、 sodium hypochlorite 、 sodium methylate 作用下， 反应 7.0h， 生成 阿卡地新
  参考文献：
  名称：

  Nucleosides from carbohydrate adducts of diaminomaleonitrile. A novel synthesis of 5-amino-1-(.beta.-D-ribofuranosyl)imidazole-4-carboxamide and 5-amino-1-(.beta.-D-ribopyranosyl)imidazole-4-carboxamide

  摘要：

  DOI：

  10.1021/jo00206a004
• 作为产物：
  描述：

  N-formyl-N'-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonitrile 在 溶剂黄146 作用下， 以 苯 为溶剂， 反应 10.0h， 以63%的产率得到1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole
  参考文献：
  名称：

  Nucleosides from carbohydrate adducts of diaminomaleonitrile. A novel synthesis of 5-amino-1-(.beta.-D-ribofuranosyl)imidazole-4-carboxamide and 5-amino-1-(.beta.-D-ribopyranosyl)imidazole-4-carboxamide

  摘要：

  DOI：

  10.1021/jo00206a004

文献信息

• Purine nucleoside analogues for treating flaviviridae including hepatitis C
  申请人：Idenix Pharmaceuticals, Inc.

  公开号：US09186369B2

  公开（公告）日：2015-11-17

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-HCV biologically active pentofuranonucleoside where the pentofuranonucleoside base is an optionally substituted 2-azapurine. The optionally substituted pentofuranonucleoside, or a salt or prodrug thereof, may be administered alone or in combination with one or more optionally substituted pentofuranonucleosides or other anti-viral agents.

  这项发明涉及一种治疗宿主，特别是感染丙型肝炎、黄病毒和/或猪瘟病毒的方法，包括向该宿主施用一种抗HCV生物活性的戊呋喃核苷的有效量，其中戊呋喃核苷的碱基是一种可选择取代的2-氮杂嘌呤。可选择取代的戊呋喃核苷，或其盐或前药，可以单独或与一个或多个可选择取代的戊呋喃核苷或其他抗病毒药剂联合使用。
• 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。
• PURINE NUCLEOSIDE ANALOGUES FOR TREATING FLAVIVIRIDAE INCLUDING HEPATITIS C
  申请人：Indenix Pharmaceuticals, Inc.

  公开号：US20140234251A1

  公开（公告）日：2014-08-21

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-HCV biologically active pentofuranonucleoside where the pentofuranonucleoside base is an optionally substituted 2-azapurine. The optionally substituted pentofuranonucleoside, or a salt or prodrug thereof, may be administered alone or in combination with one or more optionally substituted pentofuranonucleosides or other anti-viral agents.

  这项发明涉及一种治疗感染丙型肝炎病毒、黄热病毒和/或猪瘟病毒的宿主，特别是人类的方法，包括向该宿主施用一种抗HCV生物活性戊呋喃核苷，其中戊呋喃核苷碱基是一个可选择取代的2-氮杂嘌呤。可选择取代的戊呋喃核苷，或其盐或前药，可以单独或与一个或多个可选择取代的戊呋喃核苷或其他抗病毒药物联合使用。
• 10.1002/ddr.22237
  作者：Du, Xingyi、Yang, Xingxing、Zhao, Jianyuan、Zhang, Jinyan、Yu, Jiahui、Ma, Ling、Zhang, Weina、Cen, Shan、Ren, Xuhong、He, Xinhua

  DOI：10.1002/ddr.22237

  日期：——

  target for broad‐spectrum antiviral nucleoside analogues. However, after over half a century of structural modification, exploring unclaimed chemical space using frequently‐used structural substitution methods to design new nucleoside analogues is challenging. In this study, we explore the use of the “ring‐opening” strategy to design new base mimics, thereby using these base mimics to design new nucleoside

  近年来，RNA 病毒感染的全球流行给公共卫生带来了重大挑战，需要扩大其替代治疗库。由于其进化保守性，RNA 依赖性 RNA 聚合酶 (RdRp) 已成为广谱抗病毒核苷类似物的潜在靶标。然而，经过半个多世纪的结构修饰，使用常用的结构替代方法探索无人认领的化学空间来设计新的核苷类似物是具有挑战性的。在本研究中，我们探索使用“开环”策略来设计新的碱基模拟物，从而利用这些碱基模拟物设计具有广谱抗病毒活性的新核苷类似物。共合成29种化合物。它们针对病毒 RdRp 的活性最初是使用甲型流感病毒 RdRp 高通量筛选模型进行筛选的。然后，验证了38a针对流感病毒株A/PR/8/34（H1N1）的抗病毒活性，显示出50%的抑制浓度（IC 50 ）值为 9.95 μM，优于利巴韦林（阳性对照，IC 50 = 11.43 μM）。此外，38a还对冠状病毒229E具有IC抑制活性50 30.82μM。此外，化合
• A Short Synthesis of a Novel Ring-Expanded Purine and Its Nucleoside Analogue Containing the Imidazo[4,5-<i>e</i>][1,3]diazepine Ring Skeleton with Multiple Amino Substituents Attached to the 7-Membered Ring
  作者：L. Wang、A. Bhan、R. S. Hosmane、R. D. Guiles

  DOI：10.1080/15257779408013222

  日期：1994.12

  The synthesis of 4,6,8-triaminoimidazo[4,5-e][1,3]diazepine (1) and its nucleoside analogue (6) are reported. The heterocycle was prepared in a single step by condensation of 4,5-dicyanoimidazole with guanidine. The 5,7-fused ring structure of 1 was distinguished from the other possible 5:5-fused isomer 2 by preparing the N-15-labeled heterocycle (1*) and exploring its N-15-H-1 coupling patterns in both H-1 and N-15 NMR spectra. These spectral patterns also enabled establishment of the triamino tautomeric form of 1 as assigned. Compound 1, a novel ring-expanded (''fat'') analogue of purine, is anticipated to be planar and aromatic as predicted by molecular modeling. The 1-benzyl analogue (4), a protocol for the ribosyl analogue 6, was similarly prepared from 1-benzyl-4,5-dicyanoimidazole. The nucleoside 6 was prepared by the modified Vorbruggen ribosylation of 1. The position of ribosylation was unequivocally established by an unambiguous synthesis of 6 from condensation of 1-(2',3',5'-tri-O-benzoyl-beta-($) under bar D-ribofuranosyl)-4,5-dicyanoimidazole (7) with guanidine in a solution of sodium methoxide in methanol. The nucleoside 7 was prepared by the Vorbruggen ribosylation of 4,5-dicyanoimidazole.