Synthesis, Antibacterial Activity, and Molecular Docking Study of Bispyrazole‐Based Derivatives as Potential Antibacterial Agents

Abstract

Development of novel antibacterial agents is one of most important aims in the field of medicinal chemistry and drug discovery. A new series of bispyrazole derivatives were synthesized with moderate to excellent yields ranging from 68 to 83 %. The structures of the newly synthesized compounds were confirmed using NMR, GC, IR techniques. The prepared derivatives were screened against Gram-positive bacteria (S. aureus and B. subtilis) and Gram-negative bacteria (E. coli and P. aeruginosa). All of the new compounds exhibited good to moderate antibacterial activity against Gram-positive and Gram-negative bacteria compared to trimethoprim. The bispyrazole bearing (triflouromethyl)benzene 8 d showed significant antibacterial inhibition against all bacteria tested and was found to be more active than trimethoprim in term of inhibition zone. Minimum inhibitory concentration (MIC) showed that the bispyrazoles bearing (methylsulfonyl)benzene 8 c and 4-chlorobenzen 8 e showed potent inhibition activity against Staphylococcus aureus and Bacillus subtilis while The bispyrazole bearing (triflouromethyl)benzene 8 d displayed strong inhibitory activity against S. aureus, B. subtilis, E. coli and P. aeruginosa compared to trimethoprim. Molecular docking was investigated for the active compounds and showed promising lead-like characters. These compounds could be employed as prospective lead compounds for the synthesis of novel antibacterial agents with highly potency.

Design, synthesis and antibacterial evaluation of a novel class of tetrahydrobenzothiophene derivatives

“…Merck silica gel GF254 plates were used for analytical TLC. 1 H and 13 C NMR spectra were obtained on a Varian INOVA400 (400 MHz for 1 H and 101 MHz for 13 C) in CDCl 3 or DMSO-d 6 .…”

“…The structures of these compounds were characterized by 1 H NMR and 13 C NMR, as well as electrospray ionisation mass spectrometry (ESI-MS) analysis. The 1 H NMR results showed chemical shifts around 13.2 for the hydrogen on the amide, 12.3 for the hydrogen on the carboxyl group, multiple peaks between 7.5-8.0 for the hydrogen on the aromatic ring, multiple peaks between 1.2-3.0 for the hydrogen on the sixmembered ring, and around 1.0 for the hydrogen on the methyl group.…”

“…12 Therefore, it is urgent to find some new broad-spectrum antibacterial agents that can effectively overcome drug-resistant bacterial infections. Despite the efforts for new antibacterial agents, [13][14][15][16][17][18][19][20] the shortage of novel antibiotics is still a well-known issue, and developing new antibiotics is a long and slow process. According to the World Health Organization, AMR has become one of the most serious global public health threats in this century, and there is an urgent need to develop promising antibiotics.…”

Molecular docking, drug-likeness and DFT study of some modified tetrahydrocurcumins as potential anticancer agents

“…They reported that five compounds of newly synthesized have IC 50 values less than 5.95 µM. In our continuous attempts to develop novel potent bioactive agents ( Abdel-Jalil et al, 2015 , El-ajaily et al, 2019 , El-Barasi et al, 2020 , Eleya et al, 2011 , Hussain et al, 2008 , Ibad et al, 2011 , Kamel et al, 2022a , Kamel et al, 2022b , Mahal, 2015a , Mahal et al, 2010 , Mahal et al, 2011 , Mahal et al, 2015b , Mahal et al, 2015c , Mahal et al, 2019 , Mahal et al, 2021 , Marzano et al, 2022 , Mohapatra et al, 2021 , Salman et al, 2011 , Salman et al, 2020 , Salman et al, 2022 , Yang et al, 2017 , Yang et al, 2018 , Zinad et al, 2020a , Zinad et al, 2020b , Zinad et al, 2020c , Zinad et al, 2020d , Zinad et al, 2021a , Zinad et al, 2021b , Zinad et al, 2022 , Zinad et al, 2023a , Zinad et al, 2023b ), we aim at this study to investigate the molecular docking and DFT calculation of potent anticancer agents of tetrahydrocurcumin.…”

A Green Synthesis of Nitrogen Containing Novel Tetraazaaceanthrylene Derivatives Under Catalyst‐free Conditions: Docking studies, ADME and Antibacterial Activity

“…[8,9] Moreover, nitrogen-containing heterocyclic compounds are significantly found in several naturally occurring plant materials. [10] The N-heterocycles are attractive targets in organic and medicinal chemistry [11] due to their vast biological applications including anti-tumor, [12] antihypertensive, [13,14] antiulcer, antifungal, [15] anti-bacterial [16] antimalarial, and antiallergic activities. [17,18] Nowadays, one of the specific areas in green chemistry is the search for environmentally benign reaction media to replace the commonly used hazardous or toxic organic solvents/metal catalysts in chemical reactions.…”