3'-O-<(tert-butyl)dimethylsilyl>-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine | 226917-59-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 3'-O-<(tert-butyl)dimethylsilyl>-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• 英文别名: 2-(4-nitrophenyl)ethyl N-[9-[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-[[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-(hexadecanoylamino)-5-[6-[2-(4-nitrophenyl)ethoxycarbonylamino]purin-9-yl]oxolan-2-yl]methoxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]oxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]carbamate
• CAS: 226917-59-5
• 化学式: C₇₄H₁₀₅N₁₄O₂₀PSi₂
• 分子量: 1597.87
• InChiKey: KMIZHJDCKRZFGF-NAPIEKNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.28
• 重原子数：
  111
• 可旋转键数：
  43
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  432
• 氢给体数：
  4
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  3'-deoxy-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 2'-<2-(4-nitrophenyl)ethyl diisopropylphosphoramidite> 、 3'-O-<(tert-butyl)dimethylsilyl>-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 在 吡啶 、 四氮唑 、 水 、 碘 作用下， 生成 3'-deoxy-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-3'-O-<(tert-butyl)dimethylsilyl>-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(te...
  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：

  3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>ad... 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 以87%的产率得到3'-O-<(tert-butyl)dimethylsilyl>-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenylyl-<2'-P-<2-(4-nitrophenyl)ethyl>>-5'>-2'-O-<(tert-butyl)dimethylsilyl>-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