新型含吗啉基团的唑类和唑吡脒的合成

IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY
Sobhi M. Gomha, Zeinab A. Muhammad, Hassan M. Abdel‐aziz, E. E. El-Arab
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引用次数: 5

摘要

通过2-氧代-N,4-二芳基丁基-3-烯腙酰氯1a–d与吗啉反应制备了一系列新的吗啉基查尔酮2a–d。这些查尔酮分别与苯肼和硫脲反应,用作构建吡唑3a–d和3,4-二氢嘧啶-2(1H)-硫酮6的构建基。此外,通过1-吗啉-4-苯基-1-(2-苯基肼基)丁-3-烯-2-酮(2a)与许多杂环胺在催化量的乙酸存在下的反应,合成了一系列新的含有吗啉部分的唑并嘧啶衍生物11a、b、15、17、19和21。根据元素分析和光谱数据,确定了所有新合成化合物的指定结构,并讨论了它们的形成机制。与所用的标准抗肿瘤药物(顺铂)相比,所有合成的化合物对人癌症(A-549)和人肝细胞癌(HepG-2)两种抗肿瘤细胞系进行了体外活性测试,结果表明,化合物6、8c和17与顺铂相比具有良好的活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis of New Azoles and Azolopyrimidines Incorporating Morpholine Moiety as Potent Anti-Tumor Agents
A new series of morpholinyl-chalcones 2a–d was prepared by reaction of 2-oxo-N,4-diarylbut-3-enehydrazonoyl chlorides 1a–d with morpholine. These chalcones were used as a building block for constructing pyrazoles 3a–d and 3,4-dihydropyrimidine-2(1H)-thione 6 via their reaction with phenylhydrazine and thiourea, respectively. Moreover, a new series of azolopyrimidine derivatives 11a,b, 15, 17, 19, and 21 incorporating morpholine moiety were synthesized by reaction of 1-morpholino-4-phenyl-1-(2-phenylhydrazono)but-3-en-2-one (2a) with a number of heterocyclic amines in the presence of a catalytic amount of acetic acid. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. All the synthesized compounds were tested for in vitro activities against two antitumor cell lines, human lung cancer (A-549) and human hepatocellular carcinoma (HepG-2) compared with the employed standard antitumor drug (cisplatin) and the results revealed that compounds 6, 8c and 17 have promising activities compared with cisplatin.
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来源期刊
Croatica Chemica Acta
Croatica Chemica Acta 化学-化学综合
CiteScore
0.60
自引率
0.00%
发文量
3
审稿时长
18 months
期刊介绍: Croatica Chemica Acta (Croat. Chem. Acta, CCA), is an international journal of the Croatian Chemical Society publishing scientific articles of general interest to chemistry.
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