N-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide | 478921-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide
• CAS: 478921-25-4
• 化学式: C₄₂H₄₁F₃N₄O₈
• 分子量: 786.805
• InChiKey: WBPMVBGNSPFCTH-VLMMXISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  57.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  150.24
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 N-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以62%的产率得到Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(4-benzoylamino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Nucleosides and nucleotides. Part 214: thermal stability of triplexes containing 4′α-C-Aminoalkyl-2′-deoxynucleosides

  摘要：

  In order to develop novel antigene molecules forming thermally stable triplexes with target DNAs and having nuclease resistance properties, e synthesized oligodeoxynucleotides (ODNs) with various lengths of aminoalkyl-linkers at the 4'alpha position of thymidine and the aminoethyl-linker at the 4'alpha position of 2'-deoxy-5-methylcytidine. Thermal stability of triplexes between these ODNs and a DNA duplex was studied by thermal denaturation. The ODNs containing the nucleoside 2 with the aminoethyl-tinker or the nucleoside 3 with the aminopropyl-linker thermally stabilized the triplexes, whereas the ODNs containing the nucleoside I with the aminomethyl-linker or the nucleoside 4 with the 2-[N-(2-aminoethyl)carbamoyl]oxy]ethyl-linker thermally destabilized the triplexes. The ODNs containing 2 were the most efficient at stabilizing the triplexes with the target DNA. The ODNs containing 4'alpha-C-(2-aminoethyl)-2'-deoxy-5-methylcytidine (5) also efficiently stabilized the triplexes with the target DNA. Stability of the ODN containing 5 to nucleolytic hydrolysis by snake venom phosphodiesterase (a 3'-exonuclease) was Studied. It was found that the ODN containing 5 was more resistant to nucleolytic digestion by the enzyme than all unmodified ODN. In a previous paper, we reported that the ODNs containing 2 were more resistant to nucleolytic digestion by DNase I (an endonuclease) than the Unmodified ODNs. Thus, it was found that the ODNs containing 4'alpha-C-(2-aminoethyl)-2'-deoxynucleosides were good candidates for antigene molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00141-4
• 作为产物：
  描述：

  4'α-C-(2-azidoethyl)-3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)thymidine 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 34.0h， 生成 N-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide
  参考文献：
  名称：

  Nucleosides and nucleotides. Part 214: thermal stability of triplexes containing 4′α-C-Aminoalkyl-2′-deoxynucleosides

  摘要：

  In order to develop novel antigene molecules forming thermally stable triplexes with target DNAs and having nuclease resistance properties, e synthesized oligodeoxynucleotides (ODNs) with various lengths of aminoalkyl-linkers at the 4'alpha position of thymidine and the aminoethyl-linker at the 4'alpha position of 2'-deoxy-5-methylcytidine. Thermal stability of triplexes between these ODNs and a DNA duplex was studied by thermal denaturation. The ODNs containing the nucleoside 2 with the aminoethyl-tinker or the nucleoside 3 with the aminopropyl-linker thermally stabilized the triplexes, whereas the ODNs containing the nucleoside I with the aminomethyl-linker or the nucleoside 4 with the 2-[N-(2-aminoethyl)carbamoyl]oxy]ethyl-linker thermally destabilized the triplexes. The ODNs containing 2 were the most efficient at stabilizing the triplexes with the target DNA. The ODNs containing 4'alpha-C-(2-aminoethyl)-2'-deoxy-5-methylcytidine (5) also efficiently stabilized the triplexes with the target DNA. Stability of the ODN containing 5 to nucleolytic hydrolysis by snake venom phosphodiesterase (a 3'-exonuclease) was Studied. It was found that the ODN containing 5 was more resistant to nucleolytic digestion by the enzyme than all unmodified ODN. In a previous paper, we reported that the ODNs containing 2 were more resistant to nucleolytic digestion by DNase I (an endonuclease) than the Unmodified ODNs. Thus, it was found that the ODNs containing 4'alpha-C-(2-aminoethyl)-2'-deoxynucleosides were good candidates for antigene molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00141-4