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.

中文翻译：

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一些新型N1-(8-氟-4-氧代喹啉-5-基)氨基腙类化合物的合成及其抗肿瘤活性

背景：亚肼酰氯可从各自的 5-氨基-8-氟-4-氧代喹啉-3-羧酸酯获得，与仲环胺反应生成 N1-(1-乙基-8-氟-4-氧代喹啉- 5-基)氨基腙羧酸盐。背景：亚肼酰氯可从各自的 5-氨基-8-氟-4-氧代喹啉-3-羧酸酯获得，与仲环胺反应生成 N1-(1-乙基-8-氟-4-氧代喹啉- 5-基)氨基腙羧酸盐。简介：通过亚腙酰氯（ 6)，可从各自的5-氨基-8-氟-4-氧代喹啉-3-羧基化物与适当的仲环胺获得。这些新化合物通过 1H-NMR、13C-NMR 和 HRMS 光谱数据进行表征，并筛选其抗癌活性。目的：本研究旨在合成新型 N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate 衍生物，并研究其作为抗癌药物的潜力。目的：应用亚肼酰氯与适当的仲环胺的反应来合成一组新型的包含N哌嗪的N1-(1-乙基-8-氟-4-氧代喹啉-5-基)氨基甲腙羧酸盐。方法：哌嗪及相关仲环胺与N-(4-氧代喹啉-5-基)腈亚胺(1,3-偶极)直接反应8-10小时。结论：成功合成了一组新型N1-(8-氟-4-氧代喹啉-5-基)氨基腙。其中几种化合物对三种乳腺癌细胞系（MCF-7、T47D 和 MDA-MB-231）表现出中等活性，与多柔比星相比，IC50 值范围 =18-78μM 结果：产生的 1,3-偶极子在三甲胺存在下，由亚肼酰氯前体原位合成，适用于轻松合成 N1-(1-乙基-8-氟-4-氧代喹啉-5-基)氨基腙羧酸盐。结论：本研究成功合成了新型 N1-(8-氟-4-氧代喹啉-5-基)氨基腙。与阿霉素相比，所有检查的化合物均显示出中等活性，且 IC50 值在微摩尔范围内。