3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine | 226917-51-7

• 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: 3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• 英文别名: 3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• CAS: 226917-51-7
• 化学式: C₃₅H₅₁N₇O₈
• 分子量: 697.832
• InChiKey: MPNJDAHIVLRLPQ-HSRPRZCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  50.0
• 可旋转键数：
  22.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  203.86
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 在 吡啶 、 咪唑 作用下， 以 吡啶 为溶剂， 反应 67.0h， 生成 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
  参考文献：
  名称：

  Nucleotides, Part LIX, Synthesis, Characterization, and Biological Activities of New Potential Antiviral Agents: (2′ - 5′)Adenylate Trimer Analogs Containing 3′-Deoxy-3′-(hexadecanoylamino)adenosine at the 2′-Terminus

  摘要：

  Based upon 3'-amino-3'-deoxyadenosine (15), its protected 3'-hexadecanoylamino derivative 22 was chosen as starting material for the synthesis of a series of new modified 2'-5'-adenylate trimers 33-36 as potential antiviral agents. All (2'-5')A trimer analogs 33-36 inhibit HIV-1 replication as measured by the inhibition of syncytia formation and inhibition of HIV-1 reverse transcriptase activity. Compound 34 inhibits HIV-1 reverse transcription by 100% and subsequently inhibits expression of HIV-1 p24. However, compound 35 acts differently, since it does not inhibit HIV-1 reverse transcription, HIV-1 integrase, or HIV-1 p24 expression. Therefore, 35 appears to exert its inhibitory effect at a later stage of HIV-1 replication, i.e., the budding process.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<597::aid-hlca597>3.0.co;2-v
• 作为产物：
  描述：

  9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine 在 palladium on activated charcoal sodium hydroxide 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 228.33h， 生成 3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
  参考文献：
  名称：

  Nucleotides, Part LIX, Synthesis, Characterization, and Biological Activities of New Potential Antiviral Agents: (2′ - 5′)Adenylate Trimer Analogs Containing 3′-Deoxy-3′-(hexadecanoylamino)adenosine at the 2′-Terminus

  摘要：

  Based upon 3'-amino-3'-deoxyadenosine (15), its protected 3'-hexadecanoylamino derivative 22 was chosen as starting material for the synthesis of a series of new modified 2'-5'-adenylate trimers 33-36 as potential antiviral agents. All (2'-5')A trimer analogs 33-36 inhibit HIV-1 replication as measured by the inhibition of syncytia formation and inhibition of HIV-1 reverse transcriptase activity. Compound 34 inhibits HIV-1 reverse transcription by 100% and subsequently inhibits expression of HIV-1 p24. However, compound 35 acts differently, since it does not inhibit HIV-1 reverse transcription, HIV-1 integrase, or HIV-1 p24 expression. Therefore, 35 appears to exert its inhibitory effect at a later stage of HIV-1 replication, i.e., the budding process.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<597::aid-hlca597>3.0.co;2-v