4-Amino-7-[(2R,3R,4S,5S)-4-azidomethyl-5-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile | 214134-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Amino-7-[(2R,3R,4S,5S)-4-azidomethyl-5-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 214134-74-4
• 化学式: C₁₄H₁₅BrN₈O₄
• 分子量: 439.228
• InChiKey: OZYMRSDMOXVWPS-KORGGLPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  199.2
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-Amino-7-[(2R,3R,4S,5S)-4-azidomethyl-5-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以86.5%的产率得到4-Amino-7-[(2R,3R,4S,5S)-4-aminomethyl-5-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of some amino-deoxy 7-hexofuranosylpyrrolo[2,3-d]pyrimidines

  摘要：

  7-(6-amino-6-deoxy-beta-D-glucofuranosyl)-5-cyanopyrrolo[2,3-d]pyrimidine (22) and 7-(3-amino-methyl-3-deoxy-beta-D-allofuranosyl)-5-cyanopyrrolo [2,3-d]pyrimidine (28) were synthesized by sequentially coupling silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with the corresponding protected sugars 9 and 17, followed by deblocking and catalytic hydrogenation. Conversion of the 5-nitrile in 22 and 28 into a carboxamide gave the corresponding sangivamycin derivatives 23 and 29. Whereas 5'-aminomethyl nucleosides 22 and 23 inhibited the growth of four different human tumor cell lines at mu M concentrations, the 3'-aminomethyl analogs 28 and 29 were much less active against these cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00098-6
• 作为产物：
  描述：

  1-O-acetyl-3-azidomethyl-2,5,6-tri-O-benzoyl-3-deoxy-β-D-allofuranose 在 三氟甲磺酸三甲基硅酯 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 40.5h， 生成 4-Amino-7-[(2R,3R,4S,5S)-4-azidomethyl-5-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of some amino-deoxy 7-hexofuranosylpyrrolo[2,3-d]pyrimidines

  摘要：

  7-(6-amino-6-deoxy-beta-D-glucofuranosyl)-5-cyanopyrrolo[2,3-d]pyrimidine (22) and 7-(3-amino-methyl-3-deoxy-beta-D-allofuranosyl)-5-cyanopyrrolo [2,3-d]pyrimidine (28) were synthesized by sequentially coupling silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with the corresponding protected sugars 9 and 17, followed by deblocking and catalytic hydrogenation. Conversion of the 5-nitrile in 22 and 28 into a carboxamide gave the corresponding sangivamycin derivatives 23 and 29. Whereas 5'-aminomethyl nucleosides 22 and 23 inhibited the growth of four different human tumor cell lines at mu M concentrations, the 3'-aminomethyl analogs 28 and 29 were much less active against these cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00098-6