1-<2,5-O-diacetyl-3-C-(azidomethyl)-3-deoxy-β-D-erythro-pentofuranosyl>thymine | 146035-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-<2,5-O-diacetyl-3-C-(azidomethyl)-3-deoxy-β-D-erythro-pentofuranosyl>thymine
• 英文别名: 1-[2,5-O-diacetyl-3-C-(azidomethyl)-3-deoxy-β-D-erythro-pentofuranosyl]thymine；[(2S,3R,4R,5R)-4-acetyloxy-3-(azidomethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 146035-77-0
• 化学式: C₁₅H₁₉N₅O₇
• 分子量: 381.345
• InChiKey: SCGACAGHYDJCEH-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-<2,5-O-diacetyl-3-C-(azidomethyl)-3-deoxy-β-D-erythro-pentofuranosyl>thymine 在 吡啶 、 4-二甲氨基吡啶 、 氨 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 48.0h， 生成 1-[(2R,3R,4R,5S)-4-(azidomethyl)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-phenoxycarbothioyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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：

  5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose 在 四氢呋喃 、 吡啶 、 sodium hydroxide 、 叠氮化锂 、 C₄F₉SO₃K 、 硼烷 、 双氧水 、 sodium hydride 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.5h， 生成 1-<2,5-O-diacetyl-3-C-(azidomethyl)-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