Nano-MoO₃-mediated synthesis of bioactive thiazolidin-4-ones acting as anti-bacterial agents and their mode-of-action analysis using in silico target prediction, docking and similarity searching

Abstract

The efficacy of thiazolidin-4-ones as synthons for diverse biological small molecules has given impetus to anti-bacterial studies. Our work aims to synthesize novel bioactive thiazolidin-4-ones using nano-MoO 3 for the first time. The compelling advantage of using nano-MoO 3 is that the recovered nano-MoO 3 can be reused thrice without considerable loss of its catalytic activity. The synthesized thiazolidin-4-ones were tested for anti-bacterial activity against two strains of pathogenic bacteria, namely, Salmonella typhi and Klebsiella pneumoniae. Our results indicated that 3-(benzo [d]isoxazol-3-yl)-2-(3-methoxyphenyl)thiazolidine-4-one (compound 3b) showed significant inhibitory activity towards Salmonella typhi, in comparison with gentamicin.Furthermore, in silico target prediction presented the target of compound 3b as the FtsK motor domain of DNA translocase of Salmonella typhi. Hence, our hypothesis is that compound 3b may disrupt chromosomal segregation and thereby inhibit the division of Salmonella typhi. In addition, similarity searching showed that 34 compounds with a chemical similarity of 70% or higher to compound 3b, which were retrieved from ChEMBL, bound to targets associated with biological processes related to cell development in 36% of the cases. In summary, our work details novel usage of nano-MoO 3 for the synthesis of novel thiazolidin-4-ones possessing anti-bacterial activity, and presents a mode-of-action hypothesis.

Green Synthesis of Silver Nanoparticles by Cytobacillus firmus Isolated from the Stem Bark of Terminalia arjuna and Their Antimicrobial Activity

“…The antibacterial activities of the AgNPs were investigated against Escherichia coli and Staphylococcus aureus using the agar disc diffusion method as described earlier [ 23 ]. The diameters of the zones of inhibition for different concentrations of AgNPs were measured and expressed in millimeters ( Table 1 ).…”

Triazole‐Pyridine Dicarbonitrile Targets Phosphodiesterase 4 to Induce Cytotoxicity in Lung Carcinoma Cells

“…We reported the synthetic methodologies for the preparation of various bioactive heterocyclic moieties . In the present study, the green procedure for the synthesis of triazolo‐pyridine dicarbonitriles and dihydropyridine dicarbonitriles catalyzed by TBAB in water has been reported.…”

I2-DMSO-Mediated Transannulation of Benzo[d]isoxazol-3-amine: Direct Access to 2,4,5-Substituted Pyrimidine Derivatives

“…1, 156.7, 137.8 (d, J = 7.0 Hz, 3 J CF ), 134.9, 134.4, 134.1, 130.6 (d, J = 8.0 Hz, 3 J CF ), 130. 3,130.0,128.7,128.0,125.6 (d,J = 3.0 Hz,4 J CF ), 121.1 (d, J = 21.0 Hz, 2 J CF ), 119. 6,118.2,117.6,116.1 (d,J = 22.0 Hz,2 4, 190.8, 165.1, 164.1, 161.1, 156.6, 140.6, 134.9, 134.4, 134.2, 134.1, 131.0, 130.3, 130.0, 129.2, 128.7, 128.2, 119.6, 118.2, 117.6 pyrimidin-5-yl](4-bromophenyl)methanone (4an).…”

“…2 For example, Basappa's group has reported a nano-MoO 3 -mediated reaction of benzo [d]isoxazol-3-amine, aryl aldehydes, and thioglycolic acid for the synthesis of thiazolidin-4-ones (Scheme 1a). 3 In addition, because of the instability of the N−O bond, benzo [d]isoxazol-3-amines can also undergo a reductive ringopening reaction for the preparation of o-hydroxybenzamidines (Scheme 1b). 4 Recently, Liu's group has developed a novel Au(III) or Au(I)/Lewis acid-catalyzed [3+3] annulation reaction for the transannulation of benzo [d]isoxazol-3-amines (Scheme 1c).…”

“…In the first case, benzo­[ d ]­isoxazol-3-amines have been utilized for the design, synthesis, and modification of pharmaceuticals in isoxazole scaffold-retaining forms . For example, Basappa’s group has reported a nano-MoO 3 -mediated reaction of benzo­[ d ]­isoxazol-3-amine, aryl aldehydes, and thioglycolic acid for the synthesis of thiazolidin-4-ones (Scheme a) . In addition, because of the instability of the N–O bond, benzo­[ d ]­isoxazol-3-amines can also undergo a reductive ring-opening reaction for the preparation of o -hydroxybenzamidines (Scheme b) …”