3'-azido-3'-deoxythymidylyl-(5'->5')-N⁴-palmitoyl-2',3'-dideoxycytidine | 246023-10-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: 3'-azido-3'-deoxythymidylyl-(5'->5')-N⁴-palmitoyl-2',3'-dideoxycytidine
• 英文别名: [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl [(2S,5R)-5-[4-(hexadecanoylamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl hydrogen phosphate；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2S,5R)-5-[4-(hexadecanoylamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl hydrogen phosphate
• CAS: 246023-10-9
• 化学式: C₃₅H₅₅N₈O₁₀P
• 分子量: 778.843
• InChiKey: LQPNGMSOLKIECQ-IIYBCFIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  54
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  200
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxythymidylyl-(5'->5')-N⁴-palmitoyl-2',3'-dideoxycytidine 在 氨 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 72.0h， 以80%的产率得到3'-azido-3'-deoxythymidylyl-(5'->5')-2',3'-dideoxycytidine
  参考文献：
  名称：

  Synthesis and in vitro anti-HIV activities of amphiphilic heterodinucleoside phosphate derivatives containing the 2',3'-dideoxynucleosides ddC, AZT and ddI

  摘要：

  N-4-Palmitoyl-2',3'-dideoxycytidine-5'-hydrogenphosphonate was condensed with 2',3'-dideoxyinosine (ddI) and 3'-azido-2',3'-dideoxythymidine (AZT) to the amphiphilic heterodimers 2',3'-dideoxyinosinylyl-(5'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (2) and 3'-azido-2',3'-dideoxythymidylyl-(5'-->5') 2',3'-dideoxycytidine (3) which was also converted to the hydrophilic heterodimer 3'-azido-2',3'-dideoxythymidylyl-(5'-->5')-2',3'-dideoxycytidine (3a). The heterodimers exhibit strong activity against HIV wild type and an AZT-resistant virus variant. The anti-HIV activity of 3 combining AZT with pN(4)-pamddC was lower than that of 2'-deoxythymidylyl-(3'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (4) linking pN(4)-pamddC as the only antiviral monomer unit to the inactive thymidine. It is expected that the anti-HIV activities and selectivities of ddNs can be varied by their dimerization to heterodimers offering the prospect of new therapeutic modalities. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80084-1
• 作为产物：
  描述：

  N⁴-palmitoyl-2',3'-dideoxycytidine 在 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 三甲基乙酰氯 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 1.05h， 生成 3'-azido-3'-deoxythymidylyl-(5'->5')-N⁴-palmitoyl-2',3'-dideoxycytidine
  参考文献：
  名称：

  Synthesis and in vitro anti-HIV activities of amphiphilic heterodinucleoside phosphate derivatives containing the 2',3'-dideoxynucleosides ddC, AZT and ddI

  摘要：

  N-4-Palmitoyl-2',3'-dideoxycytidine-5'-hydrogenphosphonate was condensed with 2',3'-dideoxyinosine (ddI) and 3'-azido-2',3'-dideoxythymidine (AZT) to the amphiphilic heterodimers 2',3'-dideoxyinosinylyl-(5'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (2) and 3'-azido-2',3'-dideoxythymidylyl-(5'-->5') 2',3'-dideoxycytidine (3) which was also converted to the hydrophilic heterodimer 3'-azido-2',3'-dideoxythymidylyl-(5'-->5')-2',3'-dideoxycytidine (3a). The heterodimers exhibit strong activity against HIV wild type and an AZT-resistant virus variant. The anti-HIV activity of 3 combining AZT with pN(4)-pamddC was lower than that of 2'-deoxythymidylyl-(3'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (4) linking pN(4)-pamddC as the only antiviral monomer unit to the inactive thymidine. It is expected that the anti-HIV activities and selectivities of ddNs can be varied by their dimerization to heterodimers offering the prospect of new therapeutic modalities. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80084-1

文献信息

• Synthesis and in vitro anti-HIV activities of amphiphilic heterodinucleoside phosphate derivatives containing the 2',3'-dideoxynucleosides ddC, AZT and ddI
  作者：Herbert Schott、Peter S Ludwig、Andreas Immelmann、Reto A Schwendener

  DOI：10.1016/s0223-5234(99)80084-1

  日期：1999.4

  N-4-Palmitoyl-2',3'-dideoxycytidine-5'-hydrogenphosphonate was condensed with 2',3'-dideoxyinosine (ddI) and 3'-azido-2',3'-dideoxythymidine (AZT) to the amphiphilic heterodimers 2',3'-dideoxyinosinylyl-(5'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (2) and 3'-azido-2',3'-dideoxythymidylyl-(5'-->5') 2',3'-dideoxycytidine (3) which was also converted to the hydrophilic heterodimer 3'-azido-2',3'-dideoxythymidylyl-(5'-->5')-2',3'-dideoxycytidine (3a). The heterodimers exhibit strong activity against HIV wild type and an AZT-resistant virus variant. The anti-HIV activity of 3 combining AZT with pN(4)-pamddC was lower than that of 2'-deoxythymidylyl-(3'-->5')-N-4-palmitoyl-2',3'-dideoxycytidine (4) linking pN(4)-pamddC as the only antiviral monomer unit to the inactive thymidine. It is expected that the anti-HIV activities and selectivities of ddNs can be varied by their dimerization to heterodimers offering the prospect of new therapeutic modalities. (C) Elsevier, Paris.