1-{2-[3-Benzyloxy-4-hydroxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-1H-pyrimidine-2,4-dione

• 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-Benzyloxy-4-hydroxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2Z)-2-(3-benzyloxy-4-hydroxy-5-oxo-2-furylidene)ethyl]pyrimidine-2,4-dione；1-[(2Z)-2-(4-hydroxy-5-oxo-3-phenylmethoxyfuran-2-ylidene)ethyl]pyrimidine-2,4-dione
• 化学式: C₁₇H₁₄N₂O₆
• 分子量: 342.308
• InChiKey: NWGPQGGTTMQEHY-SDQBBNPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-1-(2-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidene)ethyl)pyrimidine-2,4(1H,3H)-dione 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到(Z)-1-(2-(3,4-dihydroxy-5-oxofuran-2(5H)-ylidene)ethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Antitumor Activities of Novel Pyrimidine Derivatives of 2,3-O,O-Dibenzyl-6-deoxy-l-ascorbic Acid and 4,5-Didehydro-5,6- dideoxy-l-ascorbic Acid

  摘要：

  The new pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid (8-10) were synthesized by condensation of uracil and its 5-fluoro- and 5-trifluoromethyl-substituted derivatives with 4-(5,6-epoxypropyl)-2,3-O,O-dibenzyl-L-ascorbic acid (7), while pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid (14-17) with free C-2' and C-3' hydroxy groups in the lactone ring were obtained by debenzylation of 11-13 with boron trichloride. Z-Configuration of the C4'=C5' double bond and position of the benzyl group in the lactone ring of 14 were deduced from their H-1 and C-13 NMR spectra and connectivities in COSY, ROESY, and HMBC spectra. The exact stereostructure of 13 was confirmed by its X-ray crystal structure analysis. Of all the compounds in the series, compound 16 containing a 5-fluoro-substituted uracil ring showed the most significant antitumor activities against murine leukemia L1210/0 (IC50 = 1.4 mug/mL), murine mammary carcinoma FM3A/0 (IC50 = 0.78 mug/mL), and, to a lesser extent, human T-lymphocyte cells Molt4/C8 (IC50 = 31.8 mug/mL) and CEM/0 cell lines (IC50 = 20.9 mug/mL).

  DOI：

  10.1021/jm0009540

文献信息

• Synthesis and Antitumor Activities of Novel Pyrimidine Derivatives of 2,3-<i>O</i>,<i>O</i>-Dibenzyl-6-deoxy-<scp>l</scp>-ascorbic Acid and 4,5-Didehydro-5,6- dideoxy-<scp>l</scp>-ascorbic Acid
  作者：Silvana Raić-Malić、Draženka Svedružić、Tatjana Gazivoda、Andreja Marunović、Antonija Hergold-Brundić、Ante Nagl、Jan Balzarini、Erik De Clercq、Mladen Mintas

  DOI：10.1021/jm0009540

  日期：2000.12.1

  The new pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid (8-10) were synthesized by condensation of uracil and its 5-fluoro- and 5-trifluoromethyl-substituted derivatives with 4-(5,6-epoxypropyl)-2,3-O,O-dibenzyl-L-ascorbic acid (7), while pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid (14-17) with free C-2' and C-3' hydroxy groups in the lactone ring were obtained by debenzylation of 11-13 with boron trichloride. Z-Configuration of the C4'=C5' double bond and position of the benzyl group in the lactone ring of 14 were deduced from their H-1 and C-13 NMR spectra and connectivities in COSY, ROESY, and HMBC spectra. The exact stereostructure of 13 was confirmed by its X-ray crystal structure analysis. Of all the compounds in the series, compound 16 containing a 5-fluoro-substituted uracil ring showed the most significant antitumor activities against murine leukemia L1210/0 (IC50 = 1.4 mug/mL), murine mammary carcinoma FM3A/0 (IC50 = 0.78 mug/mL), and, to a lesser extent, human T-lymphocyte cells Molt4/C8 (IC50 = 31.8 mug/mL) and CEM/0 cell lines (IC50 = 20.9 mug/mL).