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新型噻唑并[3,2-a]嘧啶衍生物的合成、表征及其抗氧化和细胞毒性活性评价

Synthesis and Characterization of Novel Thiazolo[3,2-a]pyrimidine Derivatives and Evaluation of Antioxidant and Cytotoxic Activities.

作者信息

Khalilpour Asieh, Asghari Sakineh, Pourshab Maryam

机构信息

Department of Environmental Health Engineering, Faculty of Paramedical Sciences, Babol University of Medicinal Sciences, Babol, 47176-47745, Iran.

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

出版信息

Chem Biodivers. 2019 May;16(5):e1800563. doi: 10.1002/cbdv.201800563. Epub 2019 Apr 11.

Abstract

A series of novel thiazolo[3,2-a]pyrimidines were synthesized and characterized by FT-IR, H, C-NMR and mass techniques. Their antioxidant activities were investigated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay and the results showed that all the synthesized compounds exhibit good antioxidant activity. In addition, it was found that any substituent on the aromatic ring of the products plays an important role in their antioxidant activity. In vitro cytotoxicity of compounds 4a-4j was investigated using MTT cell viability assay. Among these compounds, 6-ethyl 2,3-dimethyl 5-(4-chlorophenyl)-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-2,3,6-tricarboxylate (4e) bearing a chlorine substituent displayed the highest cytotoxic effect (IC =6.26±0.6 μm) in comparison with doxorubicin (IC =0.68±0.1 μm) as a standard after 72 h. Therefore, it is assumed that these compounds could be used as effective antioxidant and cytotoxic agents.

摘要

合成了一系列新型噻唑并[3,2 - a]嘧啶,并通过傅里叶变换红外光谱(FT - IR)、氢谱(¹H)、碳谱(¹³C) - 核磁共振(NMR)和质谱技术对其进行了表征。通过1,1 - 二苯基 - 2 - 苦基肼(DPPH)自由基清除试验研究了它们的抗氧化活性,结果表明所有合成的化合物均表现出良好的抗氧化活性。此外,还发现产物芳环上的任何取代基对其抗氧化活性都起着重要作用。使用MTT细胞活力测定法研究了化合物4a - 4j的体外细胞毒性。在这些化合物中,带有氯取代基的6 - 乙基 - 2,3 - 二甲基 - 5 -(4 - 氯苯基) - 7 - 甲基 - 2,3 - 二氢 - 5H - [1,3]噻唑并[3,2 - a]嘧啶 - 2,3,6 - 三羧酸酯(4e)在72小时后与作为标准的阿霉素(IC₅₀ =

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