In the present study, coumarin‐bearing three pyridinium and three tetra‐alkyl ammonium salts were synthesized. The compounds were fully characterized by 1H‐ and 13C‐NMR, LC/MS and IR spectroscopic methods and elemental analyses. The cytotoxic properties of all compounds were tested against human liver cancer (HepG2), human colorectal cancer (Caco‐2) and non‐cancer mouse fibroblast (L‐929) cell lines. Some compounds performed comparable cytotoxicity with standard drug cisplatin. Antibacterial properties of the compounds were tested against Gram‐negative Escherichia coli and Gram‐positive Bacillus subtilis bacteria, but the compounds did not have any antibacterial effect against both bacteria. Enzyme inhibitory properties of all compounds were tested on the activities of human carbonic anhydrase I and II, and xanthine oxidase. All compounds inhibited both enzymes more effectively than standard drugs, acetazolamide and allopurinol, respectively. The biological evaluation results showed that ionic and water soluble coumarin derivatives are promising structures for further investigations especially on enzyme inhibition field.

中文翻译：

---

水溶性香豆素季铵氯化物：合成与生物学评价

在本研究中，合成了带有香豆素的三吡啶鎓和三种四烷基铵盐。通过 1H- 和 13C-NMR、LC/MS 和 IR 光谱方法以及元素分析对化合物进行了全面表征。测试了所有化合物对人肝癌 (HepG2)、人结直肠癌 (Caco-2) 和非癌小鼠成纤维细胞 (L-929) 细胞系的细胞毒性。一些化合物的细胞毒性与标准药物顺铂相当。化合物对革兰氏阴性大肠杆菌和革兰氏阳性枯草芽孢杆菌的抗菌特性进行了测试，但这些化合物对这两种细菌都没有任何抗菌作用。用人碳酸酐酶 I 和 II 以及黄嘌呤氧化酶的活性测试了所有化合物的酶抑制特性。所有化合物分别比标准药物乙酰唑胺和别嘌呤醇更有效地抑制这两种酶。生物学评价结果表明，离子和水溶性香豆素衍生物是进一步研究特别是酶抑制领域的有前途的结构。