6-(4,5-dihydro-4-hydroxy-4-methylthiazol-2-yl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine | 865998-88-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-(4,5-dihydro-4-hydroxy-4-methylthiazol-2-yl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-(4-hydroxy-4-methyl-5H-1,3-thiazol-2-yl)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 865998-88-5
• 化学式: C₂₀H₂₃N₅O₈S
• 分子量: 493.497
• InChiKey: VMDIVUBLMXEMCB-WSNJFSJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-(4,5-dihydro-4-hydroxy-4-methylthiazol-2-yl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以84%的产率得到6-(4-methylthiazol-2-yl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

  摘要：

  Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine ribonucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl (3k) or 2-furyl (3g) groups exerting EC90 = 0.14 and 0.4 mu M, respectively.

  DOI：

  10.1021/jm050335x
• 作为产物：
  描述：

  9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine-6-carbonitrile 在 吡啶 、 硫化氢 、 sodium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 6-(4,5-dihydro-4-hydroxy-4-methylthiazol-2-yl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

  摘要：

  Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine ribonucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl (3k) or 2-furyl (3g) groups exerting EC90 = 0.14 and 0.4 mu M, respectively.

  DOI：

  10.1021/jm050335x

文献信息

• Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides
  作者：Michal Hocek、Petr Nauš、Radek Pohl、Ivan Votruba、Phillip A. Furman、Phillip M. Tharnish、Michael J. Otto

  DOI：10.1021/jm050335x

  日期：2005.9.1

  Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine ribonucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl (3k) or 2-furyl (3g) groups exerting EC90 = 0.14 and 0.4 mu M, respectively.