N⁶-benzoyl-O^P-(2-cyanoethyl)-3'-deoxyadenylyl-(2'->5')-N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester | 486424-72-0

• 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-O^P-(2-cyanoethyl)-3'-deoxyadenylyl-(2'->5')-N⁶-benzoyl-3'-deoxy-2'-adenylic acid 2-{[6-(benzoylamino)-9H-purin-9-yl]methoxy}ethyl 2-cyanoethyl ester
• 英文别名: [(2R,3R,5S)-2-(6-benzamidopurin-9-yl)-5-[[[(2R,3R,5S)-2-(6-benzamidopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]oxolan-3-yl] 2-[(6-benzamidopurin-9-yl)methoxy]ethyl 2-cyanoethyl phosphate
• CAS: 486424-72-0
• 化学式: C₅₅H₅₃N₁₇O₁₅P₂
• 分子量: 1254.08
• InChiKey: ZRPGWMIFXXUKPD-COYRFMIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  89.0
• 可旋转键数：
  28.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  403.12
• 氢给体数：
  4.0
• 氢受体数：
  29.0

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-O^P-(2-cyanoethyl)-3'-deoxyadenylyl-(2'->5')-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83%的产率得到
  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：

  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 在 水 、 溶剂黄146 作用下， 反应 0.5h， 以79%的产率得到N⁶-benzoyl-O^P-(2-cyanoethyl)-3'-deoxyadenylyl-(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