1-[5-(hept-1''-yn-1''-yl)uracil-1-yl]-2(Z)-(2',3'-di-O-benzyl-2'-buten-4'-olidylidene)ethane

• 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-[5-(hept-1''-yn-1''-yl)uracil-1-yl]-2(Z)-(2',3'-di-O-benzyl-2'-buten-4'-olidylidene)ethane
• 英文别名: 5-hept-1-ynyl-1-[(2Z)-2-[5-oxo-3,4-bis(phenylmethoxy)furan-2-ylidene]ethyl]pyrimidine-2,4-dione
• 化学式: C₃₁H₃₀N₂O₆
• 分子量: 526.589
• InChiKey: BCBIQDAVQVFABQ-ITYLOYPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[5-(hept-1''-yn-1''-yl)uracil-1-yl]-2(Z)-(2',3'-di-O-benzyl-2'-buten-4'-olidylidene)ethane 在 copper(l) iodide 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以79 mg的产率得到3-[(2Z)-2-[5-oxo-3,4-bis(phenylmethoxy)furan-2-ylidene]ethyl]-6-pentylfuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Antiviral and Cytostatic Evaluations of the New C-5 Substituted Pyrimidine and Furo[2,3-d]pyrimidine 4‘,5‘-Didehydro-l-ascorbic Acid Derivatives

  摘要：

  The novel C-5 alkynyl substituted pyrimidine (1-11) and furo[2,3-d] pyrimidine derivatives (12-22) of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4',5'- didehydro-5',6'-dideoxy-L-ascorbic acid with terminal alkynes by using Sonogashira cross-coupling reaction conditions. The new compounds were evaluated for their cytostatic and antiviral activities. Among all evaluated compounds, the octynyl-substituted uracil derivative of L-ascorbic acid (3) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50 = 2-12 mu M). Pyrimidine derivatives of L-ascorbic acid containing p-substituted phenylacetylene groups (8-11) displayed also a rather pronounced (IC50 = 3- 37 mu M) inhibitory effect toward all tumor cell lines. From the bicyclic series of compounds, 6-butylfuro[ 2,3-d] pyrimidine derivative (12) and 6-p-bromophenylfuro[2,3-d] pyrimidine derivative (19) showed the highest cytostatic activity (IC50) 4.5- 20 mu M), particularly against malignant leukemia (L1210) and T-lymphocyte (Molt4/C8 and CEM) cells. Compounds 3 and 9 showed specific albeit moderate activity against cytomegalovirus (CMV, Davis strain, EC50 = 1.8 and 3.8 AM, respectively, for compounds 3 and 9) at a similar to 5-fold lower concentration than that required to show cytotoxicity.

  DOI：

  10.1021/jm070324z
• 作为产物：
  描述：

  5,6-di-O-acetyl-2,3-di-O-benzyl-L-ascorbic acid 在 copper(l) iodide 、 四(三苯基膦)钯 硫酸氢铵 、 N,N-二异丙基乙胺 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-[5-(hept-1''-yn-1''-yl)uracil-1-yl]-2(Z)-(2',3'-di-O-benzyl-2'-buten-4'-olidylidene)ethane
  参考文献：
  名称：

  Synthesis and Antiviral and Cytostatic Evaluations of the New C-5 Substituted Pyrimidine and Furo[2,3-d]pyrimidine 4‘,5‘-Didehydro-l-ascorbic Acid Derivatives

  摘要：

  The novel C-5 alkynyl substituted pyrimidine (1-11) and furo[2,3-d] pyrimidine derivatives (12-22) of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4',5'- didehydro-5',6'-dideoxy-L-ascorbic acid with terminal alkynes by using Sonogashira cross-coupling reaction conditions. The new compounds were evaluated for their cytostatic and antiviral activities. Among all evaluated compounds, the octynyl-substituted uracil derivative of L-ascorbic acid (3) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50 = 2-12 mu M). Pyrimidine derivatives of L-ascorbic acid containing p-substituted phenylacetylene groups (8-11) displayed also a rather pronounced (IC50 = 3- 37 mu M) inhibitory effect toward all tumor cell lines. From the bicyclic series of compounds, 6-butylfuro[ 2,3-d] pyrimidine derivative (12) and 6-p-bromophenylfuro[2,3-d] pyrimidine derivative (19) showed the highest cytostatic activity (IC50) 4.5- 20 mu M), particularly against malignant leukemia (L1210) and T-lymphocyte (Molt4/C8 and CEM) cells. Compounds 3 and 9 showed specific albeit moderate activity against cytomegalovirus (CMV, Davis strain, EC50 = 1.8 and 3.8 AM, respectively, for compounds 3 and 9) at a similar to 5-fold lower concentration than that required to show cytotoxicity.

  DOI：

  10.1021/jm070324z

文献信息

• Synthesis and Antiviral and Cytostatic Evaluations of the New C-5 Substituted Pyrimidine and Furo[2,3-<i>d</i>]pyrimidine 4‘,5‘-Didehydro-<scp>l</scp>-ascorbic Acid Derivatives
  作者：Tatjana Gazivoda、Mario Šokčević、Marijeta Kralj、Lidija Šuman、Krešimir Pavelić、Erik De Clercq、Graciela Andrei、Robert Snoeck、Jan Balzarini、Mladen Mintas、Silvana Raić-Malić

  DOI：10.1021/jm070324z

  日期：2007.8.1

  The novel C-5 alkynyl substituted pyrimidine (1-11) and furo[2,3-d] pyrimidine derivatives (12-22) of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4',5'- didehydro-5',6'-dideoxy-L-ascorbic acid with terminal alkynes by using Sonogashira cross-coupling reaction conditions. The new compounds were evaluated for their cytostatic and antiviral activities. Among all evaluated compounds, the octynyl-substituted uracil derivative of L-ascorbic acid (3) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50 = 2-12 mu M). Pyrimidine derivatives of L-ascorbic acid containing p-substituted phenylacetylene groups (8-11) displayed also a rather pronounced (IC50 = 3- 37 mu M) inhibitory effect toward all tumor cell lines. From the bicyclic series of compounds, 6-butylfuro[ 2,3-d] pyrimidine derivative (12) and 6-p-bromophenylfuro[2,3-d] pyrimidine derivative (19) showed the highest cytostatic activity (IC50) 4.5- 20 mu M), particularly against malignant leukemia (L1210) and T-lymphocyte (Molt4/C8 and CEM) cells. Compounds 3 and 9 showed specific albeit moderate activity against cytomegalovirus (CMV, Davis strain, EC50 = 1.8 and 3.8 AM, respectively, for compounds 3 and 9) at a similar to 5-fold lower concentration than that required to show cytotoxicity.