5-[(12-Amino-dodecylamino)-methyl]-1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione

• 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: 5-[(12-Amino-dodecylamino)-methyl]-1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• 英文别名: 5-[(12-aminododecylamino)methyl]-1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
• 化学式: C₂₂H₃₈N₄O₄
• 分子量: 422.568
• InChiKey: AEBSBTDOYIIPRK-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟乙酸乙酯 、 5-[(12-Amino-dodecylamino)-methyl]-1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione 在 4-二甲氨基吡啶 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以50 mg的产率得到2',3'-didehydro-2',3'-dideoxy-5-[N-(12-trifluoroacetylaminododecyl)aminomethyl]-uridine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms

  摘要：

  A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of "different sizes". Reactions of the 2',3'-didehydro2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

  DOI：

  10.1080/15257770008033040
• 作为产物：
  描述：

  3',5'-di-O-acetyl-2'-bromo-2'-deoxy-5-acetoxymethyl-uridine 在 三甲基氯硅烷 、 氨 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 34.1h， 生成 5-[(12-Amino-dodecylamino)-methyl]-1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms

  摘要：

  A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of "different sizes". Reactions of the 2',3'-didehydro2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

  DOI：

  10.1080/15257770008033040

文献信息

• Synthesis of Novel C-5 Substituted d4t Analogues Bearing Linker Arms as Potential Anti-HIV Agents
  作者：D. Ladurée、C. Fossey、M. Renoud-grappin、G. Fontaine、F. Camara、D. Gavriliu、A. Ciurea、A. M. Aubertin、A. Kirn

  DOI：10.1080/15257779908041592

  日期：1999.4

  This work reports the synthesis of 2',3'-didehydro-2',3'-dideoxy-thymidine analogues bearing several kinds of amino-linker arms at the C-5 position of the pyrimidine moiety. C-5 is an attractive position since a flexible chain may permit the triphosphates to be generated. The beta-D- and beta-L-d4T analogues were synthesized following a multi-step reaction from D-ribose and D-xylose, from D- and L-arabinose (towards an oxazoline ring) or from uridine and then were reacted with alkylene diamines.
• Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms
  作者：D. Gavriliu、C. Fossey、G. Fontaine、S. Benzaria、A. Ciurea、Z. Delbederi、B. Lelong、D. Ladurée、A. M. Aubertin、A. Kirn

  DOI：10.1080/15257770008033040

  日期：2000.5

  A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of "different sizes". Reactions of the 2',3'-didehydro2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.