7-<6'-deoxy-2',3',5'-tris-O-(p-nitrobenzoyl)-α-L-talofuranosyl>hypoxanthine | 86527-17-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 7-<6'-deoxy-2',3',5'-tris-O-(p-nitrobenzoyl)-α-L-talofuranosyl>hypoxanthine
• 英文别名: [(2R,3R,4R,5R)-4-(4-nitrobenzoyl)oxy-2-[(1S)-1-(4-nitrobenzoyl)oxyethyl]-5-(6-oxo-1H-purin-7-yl)oxolan-3-yl] 4-nitrobenzoate
• CAS: 86527-17-5
• 化学式: C₃₂H₂₃N₇O₁₄
• 分子量: 729.573
• InChiKey: UFILGKHSQWMCTG-VXPINWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  285
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  7-<6'-deoxy-2',3',5'-tris-O-(p-nitrobenzoyl)-α-L-talofuranosyl>hypoxanthine 在 氨 作用下， 反应 48.0h， 以63%的产率得到7-(6'-deoxy-α-L-talofuranosyl)hypoxanthine
  参考文献：
  名称：

  Synthesis and antitumor activity of 7- and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-hypoxanthine and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-6-thiopurine

  摘要：

  Reaction of 6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-L-talofuranosyl bromide (1) with the trimethylsilyl derivative of hypoxanthine, followed by removal of blocking groups, afforded 9- (6) and 7-(6'-deoxy-alpha-L-talofuranosyl)hypoxanthine (7). A study of the published optical rotations and circular dichroic (CD) spectra of pentofuranosylpurines and of (6'-deoxy-beta-D-allo- and -alpha-L-talofuranosyl)purines prepared here suggests that the sign of rotation and the sign of the longer wavelength Cotton effect is determined solely by the configuration of C-1' and its position of attachment to the purine ring. For C-1' R nucleosides, the sign is negative for N-9-linked purine nucleosides and positive for the N-7-linked isomers, and vice versa for C-1'S purine nucleosides. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 4, which upon treatment with thiourea and deblocking yielded 9-(6'-deoxy-alpha-L-talofuranosyl)-6-thiopurine (8). Unlike the previously prepared 7-(6'-deoxy-beta-D-allofuranosyl) hypoxanthine which strongly inhibited purine nucleoside phosphorylase, compounds 6-8 did not inhibit this enzyme. Compound 8 significantly inhibited the growth of L1210 tumor cells in vitro and in vivo.

  DOI：

  10.1021/jm00364a032
• 作为产物：
  描述：

  6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-α-L-talofuranosyl bromide 、 9-三甲硅基-6-[(三甲硅基)氧]基-9H-嘌呤 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以20%的产率得到7-<6'-deoxy-2',3',5'-tris-O-(p-nitrobenzoyl)-α-L-talofuranosyl>hypoxanthine
  参考文献：
  名称：

  Synthesis and antitumor activity of 7- and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-hypoxanthine and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-6-thiopurine

  摘要：

  Reaction of 6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-L-talofuranosyl bromide (1) with the trimethylsilyl derivative of hypoxanthine, followed by removal of blocking groups, afforded 9- (6) and 7-(6'-deoxy-alpha-L-talofuranosyl)hypoxanthine (7). A study of the published optical rotations and circular dichroic (CD) spectra of pentofuranosylpurines and of (6'-deoxy-beta-D-allo- and -alpha-L-talofuranosyl)purines prepared here suggests that the sign of rotation and the sign of the longer wavelength Cotton effect is determined solely by the configuration of C-1' and its position of attachment to the purine ring. For C-1' R nucleosides, the sign is negative for N-9-linked purine nucleosides and positive for the N-7-linked isomers, and vice versa for C-1'S purine nucleosides. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 4, which upon treatment with thiourea and deblocking yielded 9-(6'-deoxy-alpha-L-talofuranosyl)-6-thiopurine (8). Unlike the previously prepared 7-(6'-deoxy-beta-D-allofuranosyl) hypoxanthine which strongly inhibited purine nucleoside phosphorylase, compounds 6-8 did not inhibit this enzyme. Compound 8 significantly inhibited the growth of L1210 tumor cells in vitro and in vivo.

  DOI：

  10.1021/jm00364a032