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Synthesis and evaluation of antimicrobial and anticancer activities of 3‐phenyl‐1‐phenylsulfonyl pyrazoles containing an aminoguanidine moiety
Author(s) -
Huang Yushan,
Hu Hongmei,
Yan Rui,
Lin Liwen,
Song Mingxia,
Yao Xiaodong
Publication year - 2021
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000165
Subject(s) - antimicrobial , chemistry , moiety , staphylococcus aureus , cytotoxicity , multiple drug resistance , bacillus subtilis , minimum inhibitory concentration , docking (animal) , escherichia coli , stereochemistry , antibacterial activity , antibiotics , biochemistry , in vitro , bacteria , biology , medicine , organic chemistry , nursing , gene , genetics
A series of 3‐phenyl‐1‐phenylsulfonyl pyrazoles containing an aminoguanidine moiety was designed, synthesized, and evaluated for their antimicrobial and anticancer activities. The majority of the target compounds showed broad‐spectrum antimicrobial activity against the tested strains, with minimum inhibitory concentration (MIC) values ranging from 2 to 64 μg/ml. Compound 5k , showing the most potent antimicrobial activity against Bacillus subtilis CMCC 63501 and multidrug‐resistant Staphylococcus aureus ATCC 43300 with an MIC value of 2 μg/ml, was the most promising one in this series. It was also effective for S. aureus ATCC 33591 and multidrug‐resistant Escherichia coli ATCC BAA‐196 at higher concentrations. The bactericidal time–kill kinetics test illustrated that compound 5k had rapid bactericidal potential. Docking results exhibited that compound 5k showed various kinds of binding to the FabH receptor, reflecting that 5k could bind with the active site well. All compounds showed excellent activity against the investigated cancer cells, with IC 50 values ranging from 1.90 to 54.53 µM. Among them, compound 5f showed prominent cytotoxicity with IC 50 = 1.90 µM against A549 cells, while exhibiting lower inhibitory activity against 293T cells (IC 50 = 41.72 µM), indicating that it has the potential for a good therapeutic index as an anticancer drug.