6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine | 130469-50-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine
• 英文别名: [(2S,3R,4R,5R)-4-acetyloxy-2-(benzoyloxymethyl)-5-(6-chloropurin-9-yl)oxolan-3-yl]methyl benzoate
• CAS: 130469-50-0
• 化学式: C₂₇H₂₃ClN₄O₇
• 分子量: 550.955
• InChiKey: YXDOYYHADSYOJZ-KLPRUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 氨 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 67.08h， 生成 9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity

  摘要：

  Two ring-expanded analogues (compounds 2 and 3) of the anti-HIV fermentation product oxetanocin A (1) were synthesized from commercially available diacetone D-glucose. Antiviral testing against HIV in ATH8 cells revealed that the ring-expanded analogue 2 possessed a similar activity profile as oxetanocin A. Neither compound, however, was capable of providing full protection to the cells against HIV infection. The isomeric ring-expanded analogue 3 was totally devoid of anti-HIV activity. Molecular modeling suggested that while oxetanocin A and compounds 2 and 3 share a large common substructure with the potent anti-HIV drug, dideoxyadenosine (ddA), the extra hydroxymethyl substituent may contribute negatively to the binding of these molecules to a critical enzyme. The negative contribution may be less important in oxetanocin and isomer 2 than in isomer 3. From these studies it would appear that both oxetane and tetrahydrofuran rings are equivalent templates to support the adenine base in terms of anti-HIV activity.

  DOI：

  10.1021/jm00105a054
• 作为产物：
  描述：

  [(3aR,5S,6R,6aR)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]methanol 在 吡啶 、 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 7.42h， 生成 6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine
  参考文献：
  名称：

  [EN] 3'-SUBSTITUTED METHYL OR ALKYNYL NUCLEOSIDES FOR THE TREATMENT OF HCV
  [FR] NUCLÉOSIDES MÉTHYLE OU ALCYNYLE SUBSTITUÉS EN POSITION 3 POUR LE TRAITEMENT DU VIRUS DE L'HÉPATITE C

  摘要：

  本文提供了用于治疗黄病毒科感染的化合物、组合物和方法，包括HCV感染。在某些实施例中，披露了核苷衍生物的化合物和组合物，可以单独或与其他抗病毒药物联合使用。在某些实施例中，所述化合物是Formula I的3'-取代甲基或炔基核苷衍生物：(I)；或其药学上可接受的盐、溶剂化合物、立体异构体形式、互变异构体形式或多形形式，其中Base、PD、RA、RB1、RB2、RC和Z如本文所定义。

  公开号：

  WO2015161137A1

文献信息

• 3′-substituted methyl or alkynyl nucleosides nucleotides for the treatment of HCV
  申请人：IDENIX PHARMACEUTICALS LLC

  公开号：US10202411B2

  公开（公告）日：2019-02-12

  Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds are 3′-substituted methyl or alkynyl nucleosides of Formula I: (I); or a pharmaceutically acceptable salt, solvate, stereoisomeric form, tautomeric form or polymorphic form thereof, wherein Base, PD, RA, RB1, RB2, RC and Z are as defined herein.

  本文提供了用于治疗黄病毒科感染（包括 HCV 感染）的化合物、组合物和方法。在某些实施方案中，公开了核苷衍生物的化合物和组合物，可单独使用或与其他抗病毒药物联合使用。在某些实施方案中，所述化合物为式I的3′-取代甲基或炔基核苷：(I)；或其药学上可接受的盐、溶液剂、立体异构体形式、同分异构体形式或多晶型形式，其中Base、PD、RA、RB1、RB2、RC和Z如本文所定义。
• TSENG, CHRISTOPHER K. -H.;MARGUEZ, VICTOR E.;MILNE, GEORGE W. A.;WYSOCKI,+, J. MED. CHEM., 34,(1991) N, C. 343-349
  作者：TSENG, CHRISTOPHER K. -H.、MARGUEZ, VICTOR E.、MILNE, GEORGE W. A.、WYSOCKI,+

  DOI：——

  日期：——
• 3'-SUBSTITUTED METHYL OR ALKYNYL NUCLEOSIDES NUCLEOTIDES FOR THE TREATMENT OF HCV
  申请人：IDENIX PHARMACEUTICALS LLC

  公开号：US20170044205A1

  公开（公告）日：2017-02-16

  Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds are 3′-substituted methyl or alkynyl nucleosides of Formula I: (I); or a pharmaceutically acceptable salt, solvate, stereoisomeric form, tautomeric form or polymorphic form thereof, wherein Base, PD, R A , R B1 , R B2 , R C and Z are as defined herein.