4-Amino-7-[(2R,3R,4R,5R)-5-((R)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile | 214134-70-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-Amino-7-[(2R,3R,4R,5R)-5-((R)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• 英文别名: 4-amino-7-[(2R,3R,4R,5R)-5-[(1R)-2-amino-1-hydroxyethyl]-3,4-dihydroxyoxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 214134-70-0
• 化学式: C₁₃H₁₆N₆O₄
• 分子量: 320.308
• InChiKey: PCGBHERSFIVBGX-RRDYINPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  177
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-Amino-7-[(2R,3R,4R,5R)-5-((R)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 在 双氧水 作用下， 以 ammonium hydroxide 为溶剂， 反应 5.0h， 以66.4%的产率得到4-Amino-7-[(2R,3R,4R,5R)-5-((R)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid amide
  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：

  6-azido-3,5-di-O-benzoyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 硫酸 、 氨 、 氢气 、 碘 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 115.5h， 生成 4-Amino-7-[(2R,3R,4R,5R)-5-((R)-2-amino-1-hydroxy-ethyl)-3,4-dihydroxy-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

文献信息

• Synthesis and in vitro antitumor activity of some amino-deoxy 7-hexofuranosylpyrrolo[2,3-d]pyrimidines
  作者：Bao-Guo Huang、Miroslav Bobek

  DOI：10.1016/s0008-6215(98)00098-6

  日期：1998.4

  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.