Microwave-assisted synthesis and antimicrobial activity of novel spiro 1,3,4-thiadiazolines from isatin derivatives |
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Authors: | Daniel Pereira da Costa Aleff Cruz de Castro Girlyanderson Araújo da Silva Claudio Gabriel Lima-Junior Francisco Patricio de Andrade Júnior Edeltrudes de Oliveira Lima Boniek Gontijo Vaz Lidya Cardoso da Silva |
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Institution: | 1. Department of Chemistry, Federal University of Paraíba, João Pessoa, Brazil;2. Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraíba, João Pessoa, Brazil;3. Department of Pharmaceutical Sciences, Federal University of Paraíba, João Pessoa, Brazil;4. Institute of Chemistry, Federal University of Goiás, Goiânia, Brazil |
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Abstract: | This work describes the synthesis of spiro 1,3,4-thiadiazolines from isatin-β-thiosemicarbazone acetylation, using microwave irradiation as a source of heating the reaction medium. N-substituted isatin derivatives were used as substrates to obtain thiosemicarbazones by adding thiosemicarbazide to the isatin ketone carbonyl. The final synthetic step was the reaction of thiosemicarbazones with acetic anhydride under microwave irradiation to get the spiro compounds. Reaction times ranged from 6 to 18 minutes resulting in yields of up to 90%. Biological assays have shown promising antibacterial and antifungal activity, especially spiro thiadiazolines derived from allylated isatins. All the proposed molecules proved to be potential drug candidates based on the results of the in silico investigation, with satisfactory drug-likeness and drug-score, respecting Lipinski's rule. The use of the microwave reactor was efficient for the synthesis of thiosemicarbazones and spiro compounds, resulting in a significant reduction in reaction times with conventional heating. Taking into account the threat of antimicrobial resistance, this work presents a series of bioactive molecules that are easily obtained via microwave reaction. |
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