4-oxo-2-thioxo-1,4-dihydro-2H-quinazoline-3-carboxylic acid ethyl ester

• 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: 4-oxo-2-thioxo-1,4-dihydro-2H-quinazoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-oxo-2-thioxo-1,2-dihydroquinazoline-3(4h)-carboxylate；ethyl 4-oxo-2-sulfanylidene-1H-quinazoline-3-carboxylate
• 化学式: C₁₁H₁₀N₂O₃S
• 分子量: 250.278
• InChiKey: TUOZUSSLRQEGQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸甲酯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 4-oxo-2-thioxo-1,4-dihydro-2H-quinazoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  新型喹唑啉酮衍生物作为可能的抗肿瘤剂

  摘要：

  报道了使用 2-异硫氰酸根合-苯甲酸甲酯 2 合成具有生物活性硫代基团的一系列新型喹唑啉酮衍生物 6-15。它们的结构已在元素分析和（IR、1H NMR 和质谱）光谱数据的基础上得到证实。对一些合成化合物对艾氏腹水癌细胞的体外抗肿瘤活性进行了初步测试。

  DOI：

  10.1080/10426500600867042

文献信息

• Uses of Anthranilic Acid for the Synthesis of Dihydroquinazolin Derivatives with Antitumor, Antiproliferative and Pim-1 kinase Activities
  作者：Rafat M. Mohareb、Peter A. Halim

  DOI：10.17344/acsi.2017.4146

  日期：——

  The reaction of anthranilic acid with ethoxycarbonylisothiocyanate gave the ethyl 4-oxo-2-thioxo-1,2-dihydroquinazoline-3(4H)-carboxylate (4). The reaction of compound 4 with hydrazine hydrate and alpha-halocarbonyl derivatives was found to give either hydrazono or S-alkylated products. Heterocyclization reactions of some of the S-alkylated derivatives 8 and 12 were carried out to afford thiazole, pyran and pyridine derivatives. The cytotoxicity of the newly synthesized compounds towards the six cancer cell lines NUGC, DLD-1, HA22T, HEP G-2, HONE-1 and MCF-7 showed that compounds 6, 8, 13, 19c-f, 21b-f, 24a and 24c with the highest cytotoxicity. The c-Met kinase inhibition for some of the selected compounds showed that compounds 8, 13, 19d, 21e, 21f and 24a were the most active compounds. Screening toward tyrosine kinases revealed that compounds 13, 21e and 24a exhibit the highest inhibitions and therefore their molecular modeling was described. In addition, compounds 13 and 24a showed the highest activities towards Pim-1 kinase.
• Novel Quinazolinone Derivatives as Possible Antitumor Agents
  作者：Saber El-Sayed Barakat、Moustafa M. Ghorab、Helmy M. Saker、Mahmoud M. Abd Rabo

  DOI：10.1080/10426500600867042

  日期：2007.1.1

  The synthesis of a novel series of quinazolinone derivatives 6–15 having the biologically active thioxo group utilizing 2-isothiocyanato-benzoic acid methyl ester 2 is reported. Their structures have been confirmed on the basis of elemental analyses and (IR, 1H NMR, and mass) spectral data. Preliminary testing for the in vitro antitumor activity of some synthesized compounds against Ehrlich Ascities

  报道了使用 2-异硫氰酸根合-苯甲酸甲酯 2 合成具有生物活性硫代基团的一系列新型喹唑啉酮衍生物 6-15。它们的结构已在元素分析和（IR、1H NMR 和质谱）光谱数据的基础上得到证实。对一些合成化合物对艾氏腹水癌细胞的体外抗肿瘤活性进行了初步测试。