1-<2-O-acetyl-5-O-benzyl-3-C-<(benzyloxy)methyl>-3-deoxy-β-D-erythro-pentofuranosyl>thymine | 133713-77-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-<2-O-acetyl-5-O-benzyl-3-C-<(benzyloxy)methyl>-3-deoxy-β-D-erythro-pentofuranosyl>thymine
• 英文别名: [(2R,3R,4R,5S)-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-4,5-bis(phenylmethoxymethyl)oxolan-3-yl] acetate
• CAS: 133713-77-6
• 化学式: C₂₇H₃₀N₂O₇
• 分子量: 494.544
• InChiKey: SABUKXFXBLQYGL-PMHJDTQVSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-<2-O-acetyl-5-O-benzyl-3-C-<(benzyloxy)methyl>-3-deoxy-β-D-erythro-pentofuranosyl>thymine 在 吡啶 、 sodium hydroxide 、 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 163.0h， 生成 1-<5-O-benzyl-3-C-<(benzyloxy)methyl>-3-deoxy-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Syntheses and biological evaluations of 3'-deoxy-3'-C-branched-chain-substituted nucleosides

  摘要：

  Various 3'-deoxy-3'-C-(hydroxymethyl)-, 3'-deoxy-3'-C-(fluoromethyl)-, 3'-deoxy-3'-C-(azidomethyl)-, and 3'-deoxy-3'-C-(aminomethyl)-substituted nucleosides (total 12 compounds) have been synthesized and evaluated against L1210, P388, S-180, and CCRF-CEM cells and HSV-1, HSV-2, and HIV-1 in culture. Only 3'-deoxy-3'-C-(hydroxymethyl)thymidine (36) was found to show significant anticancer activity against L1210, P388, S-180, and CCRF-CEM cells with ED50 values of 50, 5, 10, and 1 muM, respectively. None of these compounds demonstrated significant antiviral activity against HSV-1, HSV-2, or HIV-1. These compounds were also evaluated against thymidine kinases derived from HSV-1 (strain KOS), HSV-2 (strain 333), and mammalian (K562) cells. The thymidine kinase (HSV-1 strain KOS) was inhibited significantly by both 3'-deoxy-3'-C-(hydroxymethyl)- and 3'-deoxy-3'-C-(fluoromethyl)thymidine.

  DOI：

  10.1021/jm00055a006
• 作为产物：
  描述：

  1,2-O-diacetyl-5-O-benzyl-3-<(benzyloxy)methyl>-3-deoxy-D-ribofuranose 、 胸腺嘧啶 在 C₄F₉SO₃K 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以87%的产率得到1-<2-O-acetyl-5-O-benzyl-3-C-<(benzyloxy)methyl>-3-deoxy-β-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  Syntheses and biological evaluations of 3'-deoxy-3'-C-branched-chain-substituted nucleosides

  摘要：

  Various 3'-deoxy-3'-C-(hydroxymethyl)-, 3'-deoxy-3'-C-(fluoromethyl)-, 3'-deoxy-3'-C-(azidomethyl)-, and 3'-deoxy-3'-C-(aminomethyl)-substituted nucleosides (total 12 compounds) have been synthesized and evaluated against L1210, P388, S-180, and CCRF-CEM cells and HSV-1, HSV-2, and HIV-1 in culture. Only 3'-deoxy-3'-C-(hydroxymethyl)thymidine (36) was found to show significant anticancer activity against L1210, P388, S-180, and CCRF-CEM cells with ED50 values of 50, 5, 10, and 1 muM, respectively. None of these compounds demonstrated significant antiviral activity against HSV-1, HSV-2, or HIV-1. These compounds were also evaluated against thymidine kinases derived from HSV-1 (strain KOS), HSV-2 (strain 333), and mammalian (K562) cells. The thymidine kinase (HSV-1 strain KOS) was inhibited significantly by both 3'-deoxy-3'-C-(hydroxymethyl)- and 3'-deoxy-3'-C-(fluoromethyl)thymidine.

  DOI：

  10.1021/jm00055a006