4-Amino-5-carboxamido-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyrrolo<2,3-d>pyrimidine | 115044-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-Amino-5-carboxamido-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyrrolo<2,3-d>pyrimidine
• 英文别名: 4-amino-5-carboxamido-7-(2,3-dideoxy-β-D-glyceropentofuranosyl)pyrrolo[2,3-d]pyrimidine；7H-Pyrrolo(2,3-d)pyrimidine-5-carboxamide, 4-amino-7-(tetrahydro-5-(hydroxymethyl)-2-furanyl)-, (2R-cis)-；4-amino-7-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
• CAS: 115044-82-1
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: LUXJLFMVHQURFG-POYBYMJQSA-N

物化性质

• 熔点：
  207-208 °C
• 沸点：
  677.8±55.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  桑霉素 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 19.0~22.0 ℃ 、68.94 kPa 条件下， 反应 5.0h， 生成 4-Amino-5-carboxamido-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyrrolo<2,3-d>pyrimidine
  参考文献：
  名称：

  Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs

  摘要：

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.

  DOI：

  10.1021/jo00129a034

文献信息

• Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase
  申请人：Bhat Balkrishen

  公开号：US20120165515A1

  公开（公告）日：2012-06-28

  The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

  本发明提供了核苷酸化合物及其某些衍生物，它们是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，可用于治疗RNA依赖性RNA病毒感染。它们特别适用于作为丙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，和/或用于治疗丙型肝炎感染。本发明还描述了包含这种核苷酸化合物的药物组合物，单独或与其他对RNA依赖性RNA病毒感染活性的药剂结合使用，特别是HCV感染。还揭示了使用本发明的核苷酸化合物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。
• KRAWCZYK, STEVEN H.;TOWNSEND, LEROY B., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 97-115
  作者：KRAWCZYK, STEVEN H.、TOWNSEND, LEROY B.

  DOI：——

  日期：——
• US7202224B2
  申请人：——

  公开号：US7202224B2

  公开（公告）日：2007-04-10
• Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs
  作者：Morris J. Robins、John S. Wilson、Danuta Madej、Nicholas H. Low、Fritz Hansske、Stanislaw F. Wnuk

  DOI：10.1021/jo00129a034

  日期：1995.12

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.