N⁶-benzyl-3'-deoxy-5'-O-(monomethoxytrityl)adenosine | 486424-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁶-benzyl-3'-deoxy-5'-O-(monomethoxytrityl)adenosine
• 英文别名: (2R,3R,5S)-2-[6-(benzylamino)purin-9-yl]-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-3-ol
• CAS: 486424-58-2
• 化学式: C₃₇H₃₅N₅O₄
• 分子量: 613.716
• InChiKey: VKCIHPWLKWODTM-MFNWSBMRSA-N

物化性质

• 沸点：
  813.3±75.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  103.55
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N⁶-benzyl-3'-deoxy-5'-O-(monomethoxytrityl)adenosine 在 吡啶 、 1H-1,2,4-三唑 、 水 、 4-硝基苯甲醛肟 作用下， 以 1,4-二氧六环 为溶剂， 反应 27.5h， 生成 N⁶-benzyl-3'-deoxy-5'-O-(monomethoxytrityl)-2'-adenylic acid 2-(4-nitrophenyl)ethyl ester triethylammonium salt
  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：

  虫草素 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 N⁶-benzyl-3'-deoxy-5'-O-(monomethoxytrityl)adenosine
  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