一锅法合成新型螺环氧化吲哚及其生物活性研究。

One Pot Synthesis and Biological Activity Studies of New Spirooxindoles.

机构信息

Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran.

Department of Microbiology, Faculty of Science, University of Mazandaran, Babolsar, 47416-95447, Iran.

出版信息

Chem Biodivers. 2024 Jun;21(6):e202301942. doi: 10.1002/cbdv.202301942. Epub 2024 May 3.

Abstract

This article reports one-pot synthesis of ten novel spirooxindoles using 5-methyl-2-thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65-90 %). The structures of the synthesized compounds were deduced by H-NMR, C NMR, FT-IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby-Bauer method. According to the obtained data, the synthesized compounds show more activity against Gram-positive bacteria than Gram-negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65-94.03 %). Among them, the chlorinated derivatives (4 f-j) exhibited more antioxidant activity (84.85-94.03 %) than the other compounds (4 a-e) (56.65-74.4 %) and even ascorbic acid as a standard antioxidant compound (82.3 %).

摘要

本文报道了一种使用 5-甲基-2-硫代海因、靛红衍生物和丙二腈一锅法合成十种新型螺环氧化吲哚的方法,产率为 65-90%。通过 1H-NMR、13C-NMR、FT-IR 和质谱数据推断了合成化合物的结构。根据 Kirby-Bauer 方法,评估了化合物对两种革兰氏阳性菌(金黄色葡萄球菌和枯草芽孢杆菌)和两种革兰氏阴性菌(大肠杆菌和铜绿假单胞菌)的抗菌活性。根据获得的数据,合成的化合物对革兰氏阳性菌的活性比对革兰氏阴性菌的活性更强。此外,还通过 DPPH 自由基清除试验法测量了这些化合物的抗氧化活性,结果显示它们具有良好到优秀的活性(59.65-94.03%)。其中,氯代衍生物(4f-j)的抗氧化活性(84.85-94.03%)高于其他化合物(4a-e)(56.65-74.4%),甚至高于标准抗氧化化合物抗坏血酸(82.3%)。

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