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Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2, 6‐disubstituted imidazothiadiazole analogues
Author(s) -
Tunel Hasan,
Er Mustafa,
Alici Hakan,
Onaran Abdurrahman,
Karakurt Tuncay,
Tahtaci Hakan
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.4260
Subject(s) - chemistry , thioether , adme , phenacyl bromide , mycelium , bromide , stereochemistry , nuclear magnetic resonance spectroscopy , proton nmr , imidazole , fourier transform infrared spectroscopy , nuclear chemistry , organic chemistry , in vitro , biochemistry , botany , physics , quantum mechanics , biology
In this study, thioether‐bridged imidazo[2,1‐ b ][1,3,4]thiadiazole derivatives that contained both imidazole and 1,3,4‐thiadiazole (compounds 7a‐7i and 8a‐8i ) were synthesized from the reactions of 2‐amino‐1,3,4‐thiadiazole with phenacyl bromide ( 6a ‐ 6i ) (at yields of 59% to 74%). The structure of the synthesized compounds was characterized using 1 H NMR, 13 C NMR, Fourier‐transform infrared spectroscopy, elemental analysis, mass spectroscopy, and X‐ray diffraction analysis. Mycelial growth, mycelial growth inhibition, minimum inhibitory concentration, minimum fungicidal concentration, and lethal dose values against various plant pathogenic fungi were determined for all of the target compounds synthesized in the study. The test results showed that most of the compounds had moderate to good antifungal activity. In addition, the absorption, distribution, metabolism, excretion (ADME) parameters of the compounds were calculated, and it was observed that all of the compounds met the drug‐likeness rules in general. Finally, using docking simulations, it was found that compounds 7h , 7i , 8h , and 8i showed high affinity to PDB ID:5TZ1, which is an CYP51 antifungal target structure.