1-<2,3-dideoxy-3-(N-hydroxyamino)-3-N,5-O-methano-β-D-threo-pentofuranosyl>thymine | 147043-71-8

• 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-<2,3-dideoxy-3-(N-hydroxyamino)-3-N,5-O-methano-β-D-threo-pentofuranosyl>thymine
• 英文别名: 1-[(4aS,6R,7aR)-1-hydroxy-2,4,4a,6,7,7a-hexahydrofuro[3,2-d][1,3]oxazin-6-yl]-5-methyl-pyrimidine-2,4-dione；1-[(4aS,6R,7aR)-1-hydroxy-2,4,4a,6,7,7a-hexahydrofuro[3,2-d][1,3]oxazin-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 147043-71-8
• 化学式: C₁₁H₁₅N₃O₅
• 分子量: 269.257
• InChiKey: XPWHXCAXOARGSM-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  油酰氯 、 1-<2,3-dideoxy-3-(N-hydroxyamino)-3-N,5-O-methano-β-D-threo-pentofuranosyl>thymine 以 吡啶 为溶剂， 以86%的产率得到1-<2,3-dideoxy-3-N,5-O-methano-3-(N-oleoyloxyamino)-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Anti-HIV Derivatives of 1-(2,3-Dideoxy-3-N-hydroxyamino-β-D-threo-pentofuranosyl)thymine

  摘要：

  Representative examples of the title compounds including bicyclic analogs (7-9) in which a perhydro-1,3-oxazine is ortho-fused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HIV-1 and HIV-2 replication in CEM cells (50% inhibitory concentration: 0.80-4.3 mu g/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these beta-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HIV active nucleosides bearing this configuration.

  DOI：

  10.1080/15257779408010670
• 作为产物：
  描述：

  5'-(O-tert-butyl(dimethyl)silyl)-3'-ketothymidine 在 吡啶 、 sodium cyanoborohydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 1-<2,3-dideoxy-3-(N-hydroxyamino)-3-N,5-O-methano-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Anti-HIV Derivatives of 1-(2,3-Dideoxy-3-N-hydroxyamino-β-D-threo-pentofuranosyl)thymine

  摘要：

  Representative examples of the title compounds including bicyclic analogs (7-9) in which a perhydro-1,3-oxazine is ortho-fused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HIV-1 and HIV-2 replication in CEM cells (50% inhibitory concentration: 0.80-4.3 mu g/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these beta-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HIV active nucleosides bearing this configuration.

  DOI：

  10.1080/15257779408010670

文献信息

• Yet Another Mechanism of HIV Reverse Transcriptase Inhibition?
  作者：Jean Tronchet、Martina Zséaly、Olivier Lassout、Martin Grigorov、Annie Grouiller

  DOI：10.1080/15257779508012415

  日期：1995.5.1
• Anti-HIV Derivatives of 1-(2,3-Dideoxy-3-<i>N</i>-hydroxyamino-β-D-<i>threo</i>-pentofuranosyl)thymine
  作者：Jean M. J. Tronchet、Martina Zsély、Karel Capek、Istvan Komaromi、Michel Geoffroy、Erik De Clercq、Jan Balzarini

  DOI：10.1080/15257779408010670

  日期：1994.9

  Representative examples of the title compounds including bicyclic analogs (7-9) in which a perhydro-1,3-oxazine is ortho-fused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HIV-1 and HIV-2 replication in CEM cells (50% inhibitory concentration: 0.80-4.3 mu g/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these beta-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HIV active nucleosides bearing this configuration.