4-methoxy-3-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl)benzaldehyde

• 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: 4-methoxy-3-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl)benzaldehyde
• 英文别名: 4-methoxy-3-thyminylmethylbenzaldehyde；4-Methoxy-3-(5-methyl-2,4-dioxo-1,2,3,4-tetra-hydropyrimidin-1-ylmethyl)benzaldehyde；4-methoxy-3-[(5-methyl-2,4-dioxopyrimidin-1-yl)methyl]benzaldehyde
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: FKECNFZJGREHAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(1H-imidazol-1-ylmethyl)acetophenone 、 4-methoxy-3-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl)benzaldehyde 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以49%的产率得到(E)-1-(5-{3-[2-hydroxy-5-(1H-imidazol-1-ylmethyl)phenyl]-3-oxoprop-1-en-1-yl}-2-methoxybenzyl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents

  摘要：

  Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 mu g/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.

  DOI：

  10.1134/s1070428014120094
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 盐酸 、 (1-丁基)三乙基溴化铵 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 4-methoxy-3-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl)benzaldehyde
  参考文献：
  名称：

  New Chalcones Containing 5-Fluorouracil Exhibiting in vitro Anti-Cancer Activity

  摘要：

  介绍了十四种新型含有5-氟尿嘧啶的查尔酮的合成及其细胞毒性评估，其中九种查尔酮作为曼尼基基础（8a-i）通过三步反应合成，包括氯甲基化、N-烷基化和克莱森-施密特反应。其他查尔酮（14a-e）则通过1,3-二丙炔基-5-氟尿嘧啶与2',4'-二羟基查尔酮的叠加反应获得。生物测定结果显示，11种查尔酮（不包括8d、8f和8h）对四种人类癌细胞系（包括Hep-G2、RD、LU-1和FL）表现出细胞毒性，其中化合物14e对Hep-G2、RD、LU-1和FL的细胞毒性最强，IC50值分别为1.48、10.59、3.64和7.02 μg/mL。

  DOI：

  10.2174/1570178612666150226230109

文献信息

• New Chalcones Containing 5-Fluorouracil Exhibiting in vitro Anti-Cancer Activity
  作者：Luu Chinh、Truong Hung、Nguyen Nga、Le phong、Le Cuong、Vu Chinh、Soo Kim、Tran Vu

  DOI：10.2174/1570178612666150226230109

  日期：2015.3.24

  The synthesis and cytotoxicity evaluation of fourteen new chalcones containing 5-fluorouracil were introduced in which nine chalcones as Mannich bases 8a-i were synthesized from 2'-hydroxyacetophenone (1) in three steps including chloromethylation, N-alkylation and Claisen-Schmidt reactions. Other chalcones 14a-e were obtained from Click reaction between 1,3-dipropargyl-5-fluorouracil and azide derivatives of 2',4'-dihydroxychalcone. The bio-assay results showed that 11 chalcones (excluding 8d, 8f and 8h) exhibited cytotoxicity against four human cancer cell lines including Hep-G2, RD, LU-1 and FL in which compound 14e exhibited the most potent cytotoxicity against Hep-G2, RD, LU-1 and FL with IC50 values of 1.48, 10.59, 3.64 and 7.02 μg/mL, respectively.

  介绍了十四种新型含有5-氟尿嘧啶的查尔酮的合成及其细胞毒性评估，其中九种查尔酮作为曼尼基基础（8a-i）通过三步反应合成，包括氯甲基化、N-烷基化和克莱森-施密特反应。其他查尔酮（14a-e）则通过1,3-二丙炔基-5-氟尿嘧啶与2',4'-二羟基查尔酮的叠加反应获得。生物测定结果显示，11种查尔酮（不包括8d、8f和8h）对四种人类癌细胞系（包括Hep-G2、RD、LU-1和FL）表现出细胞毒性，其中化合物14e对Hep-G2、RD、LU-1和FL的细胞毒性最强，IC50值分别为1.48、10.59、3.64和7.02 μg/mL。
• Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents
  作者：L. V. Chinh、T. N. Hung、N. T. Nga、T. T. N. Hang、T. T. N. Mai、V. A. Tarasevich

  DOI：10.1134/s1070428014120094

  日期：2014.12

  Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 mu g/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.