1-ethyl-3-(2-hydroxyeth-yl)-2,4-dioxo-(1H,3H)-quinazoline | 177363-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-ethyl-3-(2-hydroxyeth-yl)-2,4-dioxo-(1H,3H)-quinazoline
• 英文别名: 1-Ethyl-3-(2-hydroxyethyl)quinazoline-2,4-dione
• CAS: 177363-31-4
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: WSUCYOVDNYYNQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethyl-3-(2-hydroxyeth-yl)-2,4-dioxo-(1H,3H)-quinazoline 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到3-(2-Chloroethyl)-1-ethylquinazoline-2,4-dione
  参考文献：
  名称：

  4-Hydroxy-2-quinolones 173*. 1-R-3-(2-diethylamino- ethyl)-1H-quinazoline- 2,4-dione hydrochlorides as potential local anesthetic agents

  摘要：

  Different variants of the preparation and procedures in the synthesis of a series of 1-R-3-(2-dialkylaminoethyl)-1H-quinazoline-2,4-dione hydrochlorides having a structural similarity to the 4-hydroxy-2-quinolinone anesthetic chinoxicaine are discussed. A comparative analysis of the biological properties of the synthesized compounds and the known local anesthetics chinoxicaine and lidocaine is reported.

  DOI：

  10.1007/s10593-010-0475-4
• 作为产物：
  描述：

  3-(2-羟基乙基)-2,4-(1h,3h)-喹唑啉二酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以88%的产率得到1-ethyl-3-(2-hydroxyeth-yl)-2,4-dioxo-(1H,3H)-quinazoline
  参考文献：
  名称：

  4-Hydroxy-2-quinolones 173*. 1-R-3-(2-diethylamino- ethyl)-1H-quinazoline- 2,4-dione hydrochlorides as potential local anesthetic agents

  摘要：

  Different variants of the preparation and procedures in the synthesis of a series of 1-R-3-(2-dialkylaminoethyl)-1H-quinazoline-2,4-dione hydrochlorides having a structural similarity to the 4-hydroxy-2-quinolinone anesthetic chinoxicaine are discussed. A comparative analysis of the biological properties of the synthesized compounds and the known local anesthetics chinoxicaine and lidocaine is reported.

  DOI：

  10.1007/s10593-010-0475-4
• 作为试剂：
  描述：

  邻苯二甲酰甘氨酸 、 N,N'-二环己基碳二亚胺 在 1-ethyl-3-(2-hydroxyeth-yl)-2,4-dioxo-(1H,3H)-quinazoline 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到1-phthalylglycyl-1,3-dicyclohexylurea
  参考文献：
  名称：

  Synthesis of quinazolindionyl amino acid derivatives as possible antitumour agents

  摘要：

  A series of 1-ethyl-2,4-dioxo-(1H,3H)-quinazolin-3-yl amino acid and hydrazone derivatives were synthesized and tested for their antitumor activity. The alcohol and acid derivatives of quinazolindione were conjugated with the amino acid derivatives at N-3 site via ester or amide bonds by carbodiimide and azide methods. The carbodiimide-mediated amide and esterification steps were performed in the presence of HOBt or DMAP respectively otherwise the side-products N-acyl urea derivatives are formed, instead of the desired derivatives. Nine compounds exhibited encouraging antitumor activity against human liver carcinoma cell line (HepG2).[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p010.310

文献信息

• Synthesis of quinazolindionyl amino acid derivatives as possible antitumour agents
  作者：Ahmed Aboelmagd、Ezzeldin M. S. Salem、Ibrahim A. I. Ali、Mohamed S. Gomaa

  DOI：10.24820/ark.5550190.p010.310

  日期：——

  A series of 1-ethyl-2,4-dioxo-(1H,3H)-quinazolin-3-yl amino acid and hydrazone derivatives were synthesized and tested for their antitumor activity. The alcohol and acid derivatives of quinazolindione were conjugated with the amino acid derivatives at N-3 site via ester or amide bonds by carbodiimide and azide methods. The carbodiimide-mediated amide and esterification steps were performed in the presence of HOBt or DMAP respectively otherwise the side-products N-acyl urea derivatives are formed, instead of the desired derivatives. Nine compounds exhibited encouraging antitumor activity against human liver carcinoma cell line (HepG2).[GRAPHICS].
• 4-Hydroxy-2-quinolones 173*. 1-R-3-(2-diethylamino- ethyl)-1H-quinazoline- 2,4-dione hydrochlorides as potential local anesthetic agents
  作者：I. V. Ukrainets、V. V. Kravtsova、A. A. Tkach、V. I. Mamchur、E. Yu. Kovalenko

  DOI：10.1007/s10593-010-0475-4

  日期：2010.5

  Different variants of the preparation and procedures in the synthesis of a series of 1-R-3-(2-dialkylaminoethyl)-1H-quinazoline-2,4-dione hydrochlorides having a structural similarity to the 4-hydroxy-2-quinolinone anesthetic chinoxicaine are discussed. A comparative analysis of the biological properties of the synthesized compounds and the known local anesthetics chinoxicaine and lidocaine is reported.