N⁹-(6'-(N-(tert-butyloxycarbonyl)amino)-2',3'-O-isopropylidene-5',6',7',8',9'-pentadeoxy-β-D-ribo-1',4'-undecafuranosyl)adenine | 135285-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N⁹-(6'-(N-(tert-butyloxycarbonyl)amino)-2',3'-O-isopropylidene-5',6',7',8',9'-pentadeoxy-β-D-ribo-1',4'-undecafuranosyl)adenine
• 英文别名: tert-butyl N-[1-[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-6,7-dihydroxyheptan-2-yl]carbamate
• CAS: 135285-34-6；135285-41-5；135285-43-7；135285-44-8
• 化学式: C₂₄H₃₈N₆O₇
• 分子量: 522.602
• InChiKey: FBEIQCPTVXYAJC-YYCZMQGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  176.1
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N⁹-(6'-(N-(tert-butyloxycarbonyl)amino)-2',3'-O-isopropylidene-5',6',7',8',9'-pentadeoxy-β-D-ribo-1',4'-undecafuranosyl)adenine 在 三氟乙酸 作用下， 以 水 为溶剂， 生成 (2R,3S,4R,5R)-2-((S)-2-Amino-6,7-dihydroxy-heptyl)-5-(6-amino-purin-9-yl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Synthesis and biological activity of sinefungin analogs

  摘要：

  A series of nucleosides (2-4) that derive from adenosine by chain extension at the 5'-end have been synthesized starting from the known phosphonate 7. The latter was first combined with 4-pentenal to give 8, which underwent chemical manipulations to provide triacetate 11, which was found suitable for the adenylation step. Further transformations, among them the Hofmann degradation of the amide group of compound 13, and final deprotection gave nucleosides 2-4. They were considered as analogues of sinefungin (1) and tested for their antileishmanial activity together with compounds 5 and 6, which were obtained independently. All the modifications with respect to sinefungin resulted in nearly complete loss of growth inhibitory activity. These results indicate that the 9' terminal amino and carboxyl groups are necessary for the activity and that the presence of the amino group at C-6' is not sufficient to maintain the antileishmanial effect. Some of the analogues however could antagonize or reverse the inhibitory activity of sinefungin (1).

  DOI：

  10.1021/jm00113a018
• 作为产物：
  描述：

  N⁹-(6'-(N-(tert-butyloxycarbonyl)amino)-10'-ene-5',6',7',8',9',10',11'-heptadeoxy-2',3'-O-isopropylidene-β-D-ribo-1',4'-undecafuranosyl)adenine 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 乙腈 为溶剂， 以70%的产率得到N⁹-(6'-(N-(tert-butyloxycarbonyl)amino)-2',3'-O-isopropylidene-5',6',7',8',9'-pentadeoxy-β-D-ribo-1',4'-undecafuranosyl)adenine
  参考文献：
  名称：

  Synthesis and biological activity of sinefungin analogs

  摘要：

  A series of nucleosides (2-4) that derive from adenosine by chain extension at the 5'-end have been synthesized starting from the known phosphonate 7. The latter was first combined with 4-pentenal to give 8, which underwent chemical manipulations to provide triacetate 11, which was found suitable for the adenylation step. Further transformations, among them the Hofmann degradation of the amide group of compound 13, and final deprotection gave nucleosides 2-4. They were considered as analogues of sinefungin (1) and tested for their antileishmanial activity together with compounds 5 and 6, which were obtained independently. All the modifications with respect to sinefungin resulted in nearly complete loss of growth inhibitory activity. These results indicate that the 9' terminal amino and carboxyl groups are necessary for the activity and that the presence of the amino group at C-6' is not sufficient to maintain the antileishmanial effect. Some of the analogues however could antagonize or reverse the inhibitory activity of sinefungin (1).

  DOI：

  10.1021/jm00113a018