Zeolite (Y‐H)‐based green synthesis, antimicrobial activity, and molecular docking studies of imidazole bearing oxydibenzene hybrid molecules

Desai, N. C.; Maheta, Abhay; Jethawa, Aratiba M.; Pandit, Unnat; Ahmad, Iqrar; Patel, Harun

doi:10.1002/jhet.4427

Cited by 14 publications

(11 citation statements)

References 32 publications

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“…According to the National Committee for Clinical Laboratory Standards, the MIC values of all produced compounds were evaluated using the broth microdilution method. The antibacterial activity of newly synthesized compounds was tested using bacterial and fungal isolates obtained from Institute of Microbial Technology, Chandigarh [24, 25].…”

Section: Resultsmentioning

confidence: 99%

“…All the aromatic protons present in the hybrid entity had shown signals between 7.16 and 7.80 ppm. The carbon atoms present in the synthesized hybrids were recognized by 13 The antibacterial activity of newly synthesized compounds was tested using bacterial and fungal isolates obtained from Institute of Microbial Technology, Chandigarh [24,25].…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, antimicrobial evaluation, and in‐silico studies of some 4‐thiazolidinone hybrids bearing coumarin and pyridine moieties

Desai

Mehta

Jethawa

et al. 2022

Journal of Heterocyclic Chem

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Antimicrobial resistance is a major threat to mankind. Many frontline medications are ineffective against antimicrobial-resistant strains which are also responsible for the high mortality rate worldwide. The urgency to create new sets of antimicrobial agents is a priority in present circumstances. In continuation to this, we have strategically designed and synthesized some novel hybrids of 4-thiazolidinone bearing coumarin and pyridine cores for the evaluation of antimicrobial efficacy. A three-step multicomponent reaction was performed via imine formation, cyclization, and Knoevenagel condensation for the synthesis of titled compounds (5a-o). The synthesized entities were characterized through different analytical techniques, that is, IR, 1 H NMR, 13 C NMR, and mass spectra. On evaluating the potency of our synthesized hybrids, we received some promising results. Compound 5m was identified as the most potent component possessing 50 μg/ml (minimum inhibitory concentration [MIC] value) against S. aureus and 250 μg/ml (MIC value) against C. albicans strains. Further, a molecular docking study against microbial DNA gyrase was carried out to understand the binding profile of synthesized molecules, which supported their in-vitro antimicrobial activity. These data helped to gain an insight into their plausible mechanism of action. Their binding affinity scores correlated well with the in-vitro antimicrobial activities while their binding modes proposed the involvement of steric, electrostatic, and hydrogen-bonding interactions with the active site.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antimicrobial evaluation, and in‐silico studies of some 4‐thiazolidinone hybrids bearing coumarin and pyridine moieties

Desai

Mehta

Jethawa

et al. 2022

Journal of Heterocyclic Chem

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“…The binding affinities of promising compounds CA1 , CA3 , CA4 , and CA10 to hMAO-B (PDB ID: 2V5Z) and hMAO-A (PDB ID: 2Z5X) enzyme active sites were revealed using a structure-based in silico method. The Protein Preparation Wizard (PPW) program’s three-step approach of preprocessing, optimization, and protein energy minimization was used for preparing protein crystal structures. , In order to properly assign the protonation states at pH 7.4 ± 1.0 and the atom kinds, LigPrep was used to produce the ligand preparation for docking studies. The structures received bond instructions and had hydrogen atoms added to them .…”

Section: Methodsmentioning

confidence: 99%

Development of Isopropyl-Tailed Chalcones as a New Class of Selective MAO-B Inhibitors for the Treatment of Parkinson’s Disorder

Abdelgawad

Abourehab

et al. 2023

ACS Omega

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Thirteen isopropyl chalcones (CA1−CA13) were synthesized and evaluated for their inhibitory activity against monoamine oxidase (MAO). All compounds inhibited MAO-B more effectively than MAO-A. Compound CA4 most potently inhibited MAO-B with an IC 50 value of 0.032 μM, similar to that of CA3 (IC 50 = 0.035 μM) and with high selectivity index (SI) values for MAO-B over respectively). The −OH (CA4) or −F (CA3) group at the para position on the A ring provided higher MAO-B inhibition than that of the other substituents (−OH ≥ −F > −Cl > −Br > −OCH 2 CH 3 > −CF 3 ). On the other hand, compound CA10 most potently inhibited MAO-A with an IC 50 value of 0.310 μM and effectively MAO-B (IC 50 = 0.074 μM). The Br-containing thiophene substituent (CA10) instead of the A ring showed the highest MAO-A inhibition. In a kinetic study, K i values of compounds CA3 and CA4 for MAO-B were 0.076 ± 0.001 and 0.027 ± 0.002 μM, respectively, and that of CA10 for MAO-A was 0.016 ± 0.005 μM. A reversibility study showed that CA3 and CA4 were reversible inhibitors of MAO-B and CA10 was a reversible inhibitor of MAO-A. In docking and molecular dynamics, the hydroxyl group of CA4 and two hydrogen bonds contributed to the stability of the protein−ligand complex. These results suggest that CA3 and CA4 are potent reversible selective MAO-B inhibitors and can be used for the treatment of Parkinson's disease.

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“…At a physiological pH of 7.2 ± 0.2, the potential ionization states for each ligand structure were generated. The Glide module of the Schrödinger module was used to accomplish the docking, while all other parameters were left at their default settings 64 , 65 .…”

Section: Methodsmentioning

confidence: 99%

Introduction of benzyloxy pharmacophore into aryl/heteroaryl chalcone motifs as a new class of monoamine oxidase B inhibitors

Sudevan

Abdelgawad

et al. 2022

Sci Rep

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The inhibitory action of fifteen benzyloxy ortho/para-substituted chalcones (B1-B15) was evaluated against human monoamine oxidases (hMAOs). All the molecules inhibited hMAO-B isoform more potently than hMAO-A. Furthermore, the majority of the molecules showed strong inhibitory actions against hMAO-B at 10 μM level with residual activities of less than 50%. Compound B10 has an IC50 value of 0.067 μM, making it the most potent inhibitor of hMAO-B, trailed by compound B15 (IC50 = 0.12 μM). The thiophene substituent (B10) in the A-ring exhibited the strongest hMAO-B inhibition structurally, however, increased residue synthesis did not result in a rise in hMAO-B inhibition. In contrast, the benzyl group at the para position of the B-ring displayed more hMAO-B inhibition than the other positions. Compounds B10 and B15 had relatively high selectivity index (SI) values for hMAO-B (504.791 and 287.600, respectively). Ki values of B10 and B15 were 0.030 ± 0.001 and 0.033 ± 0.001 μM, respectively. The reversibility study showed that B10 and B15 were reversible inhibitors of hMAO-B. PAMPA assay manifested that the benzyloxy chalcones (B10 and B15) had a significant permeability and CNS bioavailability with Pe value higher than 4.0 × 10–6 cm/s. Both compounds were stabilized in protein–ligand complexes by the π-π stacking, which enabled them to bind to the hMAO-B enzyme's active site incredibly effectively. The hMAO-B was stabilized by B10- and B15-hMAO-B complexes, with binding energies of − 74.57 and − 87.72 kcal/mol, respectively. Using a genetic algorithm and multiple linear regression, the QSAR model was created. Based on the best 2D and 3D descriptor-based QSAR model, the following statistics were displayed: R2 = 0.9125, Q2loo = 0.8347. These findings imply that B10 and B15 are effective, selective, and reversible hMAO-B inhibitors.

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Zeolite (Y‐H)‐based green synthesis, antimicrobial activity, and molecular docking studies of imidazole bearing oxydibenzene hybrid molecules

Cited by 14 publications

References 32 publications

Design, synthesis, antimicrobial evaluation, and in‐silico studies of some 4‐thiazolidinone hybrids bearing coumarin and pyridine moieties

Design, synthesis, antimicrobial evaluation, and in‐silico studies of some 4‐thiazolidinone hybrids bearing coumarin and pyridine moieties

Development of Isopropyl-Tailed Chalcones as a New Class of Selective MAO-B Inhibitors for the Treatment of Parkinson’s Disorder

Introduction of benzyloxy pharmacophore into aryl/heteroaryl chalcone motifs as a new class of monoamine oxidase B inhibitors

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