一些新的 N1-(8-氟-4-氧代喹啉-5-基)脒酮的合成和抗肿瘤活性

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Current organic synthesis Pub Date : 2024-01-17 DOI:10.2174/0115701794282903231228055914

Hind M. A. Yahya, Jalal A. Zahra, Salim S. Sabri, Mustafa M. El-Abadelah, Sanaa Bardaweel

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引用次数: 0

摘要

背景：背景：从各自的 5-氨基-8-氟-4-氧代喹啉-3-羧酸酯中可获得的肼酰氯与仲环胺发生反应，生成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒酮羧酸酯：从相应的 5-氨基-8-氟-4-氧代喹啉-3-羧酸中获得的肼酰氯与仲环胺发生反应，生成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸盐。简介：通过从相应的 5-氨基-8-氟-4-氧代喹啉-3-羧酸酯中可获得的次氮酰氯（6）与适当的仲环胺的相互作用，合成了一组含有 N-哌嗪或相关同系物的新型 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸酯（7a-h）。通过 1H-NMR、13C-NMR 和 HRMS 光谱数据对这些新化合物进行了表征，并对其抗癌活性进行了筛选。目的：本研究旨在合成新型 N1-( 4-oxoquinolin-5-yl)amidrazone 羧酸盐衍生物，并研究其作为抗癌剂的潜力。研究目的采用肼酰氯与适当的仲环胺反应的方法，合成一组含有 N-哌嗪的新型 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸盐。方法：哌嗪和相关仲环胺与 N-(4-氧代喹啉-5-基)腈亚胺（1,3-二极）直接反应 8-10 小时：成功合成了一组新的 N1-(8-氟-4-氧代喹啉-5-基)脒酮。其中几个化合物对三种乳腺癌细胞系（MCF-7、T47D 和 MDA-MB-231）显示出中等程度的活性，与多柔比星结果相比，其 IC50 值范围为 =18-78µM：在三甲胺存在下，由其肼酰氯前体原位生成的 1,3-二极适用于简单合成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)脒腙羧酸盐。结论本研究成功合成了新型 N1-(8-氟-4-氧代喹啉-5-基)脒酮。与多柔比星相比，所有受检化合物均显示出中等活性，IC50 值在微摩尔范围内。

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Synthesis and Antitumor Activity of Some New N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones

Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. background: The hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, underwent reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized via interaction of the hy-drazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carbox-ylate, with the appropriate sec-cyclic amine. These new compounds were characterized by 1H-NMR, 13C-NMR, and HRMS spectral data and screened for their anticancer activities. Aims: This study aimed at the synthesis of novel N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate derivatives and investigated their potential as anticancer agents. Objective: The reaction of hydrazonoyl chloride with the appropriate sec-cyclic amine was applied to synthesize a novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5- yl)amidrazone carboxylates that incorporate N piperazines. Methods: A direct reaction of piperazines and related sec-cyclic amines with N-(4-oxoquinolin-5-yl)nitrile imine (1,3-dipole) was carried out for 8-10 h. conclusion: A novel set N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones were successfully synthesized. Several of these compounds showed moderate activity against three breast cancer cell lines (MCF-7, T47D, and MDA-MB-231) with IC50 values in the range =18-78µM compared to Doxorubicin Results: The 1,3-dipole, generated in situ from its hydrazonoyl chloride precursor in the presence of trimethylamine, is suitable for the facile synthesis of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Conclusion: This study led to the successful synthesis of novel N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones. All the examined compounds showed moderate activity with reasonable IC50 values in the micromolar range compared to Doxorubicin.

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来源期刊

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.