1-{2-[3,4-Bis-benzyloxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-5-phenyl-1H-pyrimidine-2,4-dione | 922704-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{2-[3,4-Bis-benzyloxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-5-phenyl-1H-pyrimidine-2,4-dione
• CAS: 922704-63-0
• 化学式: C₃₀H₂₄N₂O₆
• 分子量: 508.53
• InChiKey: XNPRXFAKLYVPJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-{2-[3,4-Bis-benzyloxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-5-phenyl-1H-pyrimidine-2,4-dione 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以49.4%的产率得到
  参考文献：
  名称：

  The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of l-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations

  摘要：

  The novel C-5 substituted uracil derivatives Of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4,5-didehydro-5,6-dideoxy-L-ascorbic acid with unsaturated stannanes under Stille reaction conditions. The new compounds were evaluated for their antitumoral and antiviral activities. Among all compounds evaluated the 5-propynyl substituted uracil derivative of L-ascorbic acid (7) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 0.2-0.78 PM). However, this compound was also cytotoxic to human normal fibroblasts WI 38. The 5-(phenylethynyl)uracil-2,3-di-O-benzylated L-ascorbic acid derivative (4) exhibited an albeit slight (IC50: 55-108 mu M), but selective inhibitory effect toward all tumor cell lines except for cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), laryngeal carcinoma (Hep-2), and colon carcinoma (SW 620), and no cytotoxicity to normal human fibroblast (WI 38). Compound 7 showed some, not highly specific, inhibitory potential against vesicular stomatitis virus, Coxsackie 134 virus, and Sindbis viruses (EC50: 1.6 mu M). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.046
• 作为产物：
  描述：

  5,6-di-O-acetyl-2,3-di-O-benzyl-L-ascorbic acid 在 bis-triphenylphosphine-palladium(II) chloride ammonium sulfate 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 1-{2-[3,4-Bis-benzyloxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-5-phenyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of l-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations

  摘要：

  The novel C-5 substituted uracil derivatives Of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4,5-didehydro-5,6-dideoxy-L-ascorbic acid with unsaturated stannanes under Stille reaction conditions. The new compounds were evaluated for their antitumoral and antiviral activities. Among all compounds evaluated the 5-propynyl substituted uracil derivative of L-ascorbic acid (7) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 0.2-0.78 PM). However, this compound was also cytotoxic to human normal fibroblasts WI 38. The 5-(phenylethynyl)uracil-2,3-di-O-benzylated L-ascorbic acid derivative (4) exhibited an albeit slight (IC50: 55-108 mu M), but selective inhibitory effect toward all tumor cell lines except for cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), laryngeal carcinoma (Hep-2), and colon carcinoma (SW 620), and no cytotoxicity to normal human fibroblast (WI 38). Compound 7 showed some, not highly specific, inhibitory potential against vesicular stomatitis virus, Coxsackie 134 virus, and Sindbis viruses (EC50: 1.6 mu M). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.046