N-benzoyl-1'-deoxy-2'-isoadenosine-3'-[(2-chlorophenyl)(N-benzoyl-3'-O-acetyl-deoxycytidine-5'-yl)]phosphate | 265137-15-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: N-benzoyl-1'-deoxy-2'-isoadenosine-3'-[(2-chlorophenyl)(N-benzoyl-3'-O-acetyl-deoxycytidine-5'-yl)]phosphate
• 英文别名: [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,4R)-4-(6-benzamidopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-(2-chlorophenoxy)phosphoryl]oxymethyl]oxolan-3-yl] acetate
• CAS: 265137-15-3
• 化学式: C₄₁H₃₈ClN₈O₁₂P
• 分子量: 901.226
• InChiKey: XDPZKKFESIDQLG-ODJACXNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  63.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  246.44
• 氢给体数：
  3.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-1'-deoxy-2'-isoadenosine-3'-[(2-chlorophenyl)(N-benzoyl-3'-O-acetyl-deoxycytidine-5'-yl)]phosphate 在 吡啶 、 氨 、 水 、 N,N'-二环己基碳二亚胺 作用下， 生成 2'-deoxycytidylyl(5'-3')-1'-deoxy-2'-isoadenosine 5'-phosphate
  参考文献：
  名称：

  Recognition and inhibition of HIV integrase by a novel dinucleotide

  摘要：

  The viral enzyme, HIV integrase, is involved in the integration of viral DNA into host cell DNA. In the quest for a small nucleotide system with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered a conceptually novel dinucleotide, pIsodApdC, which is a potent inhibitor of this key viral enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00677-0
• 作为产物：
  描述：

  2-氯苯基二氯膦 在 吡啶 、 二氯乙酸 、 2,4,6-triisopropylbenzenesulfonyl tetrazolide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.05h， 生成 N-benzoyl-1'-deoxy-2'-isoadenosine-3'-[(2-chlorophenyl)(N-benzoyl-3'-O-acetyl-deoxycytidine-5'-yl)]phosphate
  参考文献：
  名称：

  Recognition and Inhibition of HIV Integrase by Novel Dinucleotides

  摘要：

  HIV integrase is involved in the integration of viral DNA into chromosomal DNA, a biological process that occurs by a sequence involving HIV DNA splicing and subsequent integration steps. in the quest for small nucleotide systems with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered novel, nuclease-resistant dinucleotides with defined base sequences that are inhibitors of this key viral enzyme. Synthetic methodologies utilized for the syntheses of the novel dinucleotides include an excellent new phosphorylating agent.

  DOI：

  10.1021/ja992528d