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Microwave‐assisted synthesis and antimicrobial activity of novel spiro 1,3,4‐thiadiazolines from isatin derivatives
Author(s) -
Costa Daniel Pereira,
Castro Aleff Cruz,
Silva Girlyanderson Araújo,
LimaJunior Claudio Gabriel,
Andrade Júnior Francisco Patricio,
Oliveira Lima Edeltrudes,
Vaz Boniek Gontijo,
Silva Lidya Cardoso
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4213
Subject(s) - isatin , chemistry , acetic anhydride , semicarbazone , microwave irradiation , antimicrobial , combinatorial chemistry , lipinski's rule of five , organic chemistry , in silico , catalysis , biochemistry , gene
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.