Multicomponent reactions of cyanoacetanilide derivatives: Synthesis of coumarin and quinoline derivative and evaluations of their cytotoxicity

IF 1.3 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Bulletin of the Chemical Society of Ethiopia Pub Date : 2024-03-12 DOI:10.4314/bcse.v38i3.15

R. M. Mohareb, Magdy K. Zahran, Hager R. Maghraby, Amira E.M. Abdallah

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Abstract

In this study, several fused heterocyclic systems involving tetrahydrobenzopyrans 7a-i and tetrahydrobenzopyridines 9a-i were synthesized. The reactions proceed via a multicomponent reaction of different aromatic aldehydes, cyanoacetanilide derivatives, and cyclohexane-1,3-dione. All the produced compounds were tested for their anticancer activity by using six cancer cell lines such as A549, HT-29, MKN-45, U87MG, SMMC-7721 and H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. The results indicated that many synthesized derivatives were the most potent towards all the cancer cell lines used, six compounds 7e, 7f, 9b, 9d, 9e, and 9g showed the highest potency. The results obtained in this work enhance further investigations in the future. KEY WORDS: Multi-component reactions, Cyanoacetanilide, Pyran, Pyridine, Cytotoxicity Bull. Chem. Soc. Ethiop. 2024, 38(3), 739-750. DOI: https://dx.doi.org/10.4314/bcse.v38i3.15

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氰乙酰苯胺衍生物的多组分反应：香豆素和喹啉衍生物的合成及其细胞毒性评估

本研究合成了几个涉及四氢苯并吡喃 7a-i 和四氢苯并吡啶 9a-i 的融合杂环系统。这些反应通过不同芳香醛、氰乙酰苯胺衍生物和环己烷-1,3-二酮的多组分反应进行。以 A549、HT-29、MKN-45、U87MG、SMMC-7721 和 H460 等六种癌细胞系为阳性对照，利用 foretinib 和标准 MTT 法进行体外抗癌活性测试。结果表明，合成的许多衍生物对所用的所有癌细胞株都最有效，其中 6 种化合物 7e、7f、9b、9d、9e 和 9g 的效力最高。本研究获得的结果有助于今后的进一步研究。关键词：多组分反应氰乙酰苯胺吡喃吡啶细胞毒性 Bull.Chem.Soc.2024, 38(3), 739-750. DOI: https://dx.doi.org/10.4314/bcse.v38i3.15

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来源期刊

Bulletin of the Chemical Society of Ethiopia 化学-化学综合

CiteScore

2.20

自引率

8.30%

发文量

113

审稿时长

6-12 weeks

期刊介绍： The Bulletin of the Chemical Society of Ethiopia (BCSE) is a triannual publication of the Chemical Society of Ethiopia. The BCSE is an open access and peer reviewed journal. The BCSE invites contributions in any field of basic and applied chemistry.