Synthesis, antimicrobial studies, and molecular docking of some new dihydro-1,3,4-thiadiazole and pyrazole derivatives derived from dithiocarbazates

A series of 3-acetyl-2-aryl-5-methylthio-2,3-dihydro-1,3,4-thiadiazoles 3a-g, N- (4-acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide derivatives 5a-e and spiro-compound 7 was prepared from starting material dithiocarbazates using N-methylpyrrolidone (NMP) /acetic anhydride mixture. Further...

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Bibliographic Details
Published in:Synthetic communications 2021-02, Vol.51 (4), p.570-584
Main Authors: Moustafa, Amr Hassan, Ahmed, Doaa H., El-Wassimy, Mohamed T. M., Mohamed, Mamdouh F. A.
Format: Article
Language:English
Subjects:
2,3-dihydo-1,3,4-thiadiazole
Amines
Antiinfectives and antibacterials
Antimicrobial
Aromatic compounds
carbothiohydrazides
Chemical synthesis
Derivatives
dithiocarbazates
E coli
Malononitrile
Molecular docking
Pyrazole
Thiadiazoles
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Summary:A series of 3-acetyl-2-aryl-5-methylthio-2,3-dihydro-1,3,4-thiadiazoles 3a-g, N- (4-acetyl-5-aryl-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide derivatives 5a-e and spiro-compound 7 was prepared from starting material dithiocarbazates using N-methylpyrrolidone (NMP) /acetic anhydride mixture. Furthermore, a new series of 5-amino-3- (methylthio) -1-substituted-1H-pyrazole-4-carbonitrile derivatives 12a-d was prepared using two synthetic routes: (i) via reaction of bis (methylthio) methylene malononitrile 8 with carbothiohydrazides 11a-d, or (ii) via reaction of methyl 5-amino-4-cyano-3- (methylthio) -1H-pyrazole-1-carbodithioate 9a with primary/secondary amines. The antimicrobial screening of newly synthesized compounds revealed that compounds 3b, 7, and 12d are the most potent against the Gram-positive (S. aureus) and the Gram-negative (E. coli) bacteria compared to ciprofloxacin as reference drug. Mechanistically, the theoretical docking results of 3b, 7 and 12d suggested that they may act as potent inhibitors of theDNA gyrase.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1843179