N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester | 486424-67-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester
• 英文别名: N⁶-benzoyl-3'-deoxyadenylyl-{2'-[O^P-(2-cyanoethyl)]->2"}-N⁶-benzoyl-9-[(2"-hydroxyethoxy)methyl]adenine；[(2R,3R,5S)-2-(6-benzamidopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl] 2-[(6-benzamidopurin-9-yl)methoxy]ethyl 2-cyanoethyl phosphate
• CAS: 486424-67-3
• 化学式: C₃₅H₃₄N₁₁O₉P
• 分子量: 783.697
• InChiKey: YHINOEGPCBNEGQ-KEESBOICSA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  253
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-苯甲酰基-5'-O-[二(4-甲氧基苯基)苯基甲基]-3'-脱氧-腺苷 2'-[2-氰基乙基二(1-甲基乙基)亚磷酰胺] 、 N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以82%的产率得到N⁶-benzoyl-O^P-(2-cyanoethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenylyl-(2'->5')-N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester
  参考文献：
  名称：

  Nucleotides Part LXX

  摘要：

  The chemical syntheses of nuclease-resistant, nontoxic bioactive (2'-5')agonists, 3'-deoxyadenylyl-(2'-->5')3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (d(3)A-d(3)A-d(3)A-etherA; 36), 1-benzyl-3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->2")-9-[2"-hydroxyethoxy)methyl]adenine (N-1-benzyl-d(3)A-d(3)A-d(3)A-etherA; 37), N-6-benzyl-3'-deoxyadenylyl-(2'-5')3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (N-6-benzyl-d(3)Ad(3)A-d(3)A-etherA; 38), N-6-benzyladenylyl-(2'-->5')-adenylyl-(2'-->5')-adenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (N-6-benzyl-A-A-A-etherA; 39), as well as the biological activities of 37, 38, and already synthesized and published adenylyl-(2'-->5')-adenylyl-(2'-->5')-adenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (A-A-A-etherA; 40), are described. The above (2'-5')A derivatives 37-40 inhibit HIV-1 replication as measured by inhibition of syncytia formation, HIV-1 reverse transcriptase activity, or HIV-1 p24-antigen expression, with no evidence of cytotoxicity. Oligonucleotides 37, 38, and 40 were taken up intact into T cells in culture of cytoplasmic concentrations sufficient to activate the latent endoribonuclease, RNase L. N-6-Benzyl-d(3)A-d(3)A-d(3)A-etherA (38) also exerts immunostimulatory effects by increasing expression of monocyte chemotactic protein-1 (MCP-1), and, thereby, competing with HIV-1 for binding to a critical HIV-coreceptor.

  DOI：

  10.1002/1522-2675(200208)85:8<2284::aid-hlca2284>3.0.co;2-e
• 作为产物：
  描述：

  N-[9-(2-羟基乙氧基甲基)嘌呤-6-基]苯甲酰胺 在 四氮唑 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.75h， 生成 N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester
  参考文献：
  名称：

  Nucleotides Part LXX

  摘要：

  The chemical syntheses of nuclease-resistant, nontoxic bioactive (2'-5')agonists, 3'-deoxyadenylyl-(2'-->5')3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (d(3)A-d(3)A-d(3)A-etherA; 36), 1-benzyl-3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->2")-9-[2"-hydroxyethoxy)methyl]adenine (N-1-benzyl-d(3)A-d(3)A-d(3)A-etherA; 37), N-6-benzyl-3'-deoxyadenylyl-(2'-5')3'-deoxyadenylyl-(2'-->5')-3'-deoxyadenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (N-6-benzyl-d(3)Ad(3)A-d(3)A-etherA; 38), N-6-benzyladenylyl-(2'-->5')-adenylyl-(2'-->5')-adenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (N-6-benzyl-A-A-A-etherA; 39), as well as the biological activities of 37, 38, and already synthesized and published adenylyl-(2'-->5')-adenylyl-(2'-->5')-adenylyl-(2'-->2")-9-[(2"-hydroxyethoxy)methyl]adenine (A-A-A-etherA; 40), are described. The above (2'-5')A derivatives 37-40 inhibit HIV-1 replication as measured by inhibition of syncytia formation, HIV-1 reverse transcriptase activity, or HIV-1 p24-antigen expression, with no evidence of cytotoxicity. Oligonucleotides 37, 38, and 40 were taken up intact into T cells in culture of cytoplasmic concentrations sufficient to activate the latent endoribonuclease, RNase L. N-6-Benzyl-d(3)A-d(3)A-d(3)A-etherA (38) also exerts immunostimulatory effects by increasing expression of monocyte chemotactic protein-1 (MCP-1), and, thereby, competing with HIV-1 for binding to a critical HIV-coreceptor.

  DOI：

  10.1002/1522-2675(200208)85:8<2284::aid-hlca2284>3.0.co;2-e