Synthesis, antimicrobial activity and cytotoxic investigation of novel trifluoromethylated tetrazolo[1,5-a]pyrimidines

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• 作者：Elisandra Scapin ; Clarissa P. Frizzo ; Leticia V. Rodrigues…
• 关键词：Antimicrobial activities ; Tetrazolo[1 ; 5 ; a]pyrimidine ; Trifluoromethyl ; β ; alcoxyvinylketones ; Cytotoxicity activity
• 刊名：Medicinal Chemistry Research
• 出版年：2017
• 出版时间：March 2017
• 年：2017
• 卷：26
• 期：3
• 页码：640-649
• 全文大小：
• 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
• 出版者：Springer US
• ISSN：1554-8120
• 卷排序：26

文摘

A series of novel trifluoromethylated tetrazolo[1,5-a]pyrimidines were easily prepared via a highly regioselective cyclocondensation reaction between β-alkoxyvinyl trifluoromethyl ketones [CF₃C(O)CH=C(R)OMe] (in which R = Ph, 4-F–C₆H₄, 4-Cl–C₆H4, 4-Br–C₆H₄, 4-I–C₆H₄, 4-CH₃–C₆H₄, 4-OCH₃–C₆H₄, Thien-2-yl, 4-Ph–C₆H₄, Me) and 5-aminotetrazole, using conventional heating in an oil bath or microwave irradiation. The results showed that when ionic liquid was used as the reaction medium, the reaction time drastically decreased and the yield improved. Additionally, all the newly synthesized compounds were evaluated to determine their antimicrobial activity. Two of the compounds tested were the most promising because they displayed activity against the Gram-positive and Gram-negative bacteria used in the tests, and they were moderately active against the yeast Candida albicans. And finally, the cytotoxicity of lymphocytes of the two compounds was evaluated by using MTT assay. Results showed at active concentration such compounds would be safe.