Synthesis of some novel N5‐sulfonylated and N1‐alkyated pyrazole derivatives and their antimicrobial activity in conjunction with molecular docking study

Some novel N5‐sulfonylated 4 were synthesized via sulfonylation of 5‐amino‐1H‐pyrazole derivative 1 with arylsulfonyl chlorides. On the other hand, N1‐alkylated pyrazoles 7 and 10 were synthesized through alkylation of compound 1 with each of chloroacetamides and ethylchloroacetate under different c...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2020-04, Vol.57 (4), p.1698-1713
Main Authors: Metwally, Nadia H., Ragab, Eman A., Mohamed, Mona S.
Format: Article
Language:English
Subjects:
Acetic acid
Aldehydes
Alkylation
Antibiotics
Antiinfectives and antibacterials
Antimicrobial agents
Aromatic compounds
Derivatives
Klebsiella
Molecular docking
Pyrazole
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Summary:Some novel N5‐sulfonylated 4 were synthesized via sulfonylation of 5‐amino‐1H‐pyrazole derivative 1 with arylsulfonyl chlorides. On the other hand, N1‐alkylated pyrazoles 7 and 10 were synthesized through alkylation of compound 1 with each of chloroacetamides and ethylchloroacetate under different conditions. Condensation of compounds 4 and 7 with different aromatic aldehydes furnished the corresponding arylidene derivatives. In spite of, condensation of 10 with aromatic aldehydes afforded the 2‐(5‐amino‐2‐aryl‐1H‐pyrazol‐1‐yl)acetic acid. The structure of the newly synthesized compounds was elucidated by elemental analyses and spectral data. Also, the suggested mechanisms for their formation were studied. Additionally, some selected new compounds were screened against antimicrobial activity. Compound 7c exhibited a higher activity against Candida albicans (inhibition zone diameter [IZD] = 31.3 ± 0.6 mm) than the standard antibiotic Nystatin (IZD = 21 ± 0.5 mm). Also, compound 7c showed minimum inhibitory concentration = 125 and 250 μg/mL against Klebsiella pneumonia and Staphylococcus aureus, respectively. Molecular docking study also was carried out for compound 7c.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3895