Design, synthesis, antimicrobial evaluations and in silico studies of novel pyrazol-5(4H)-one and 1H-pyrazol-5-ol derivatives

Pham, Em Canh; Thi, Tuong Vi Le; Phan, Long Tieu; Nguyen, Huong-Giang Thi; Le, Khanh Nguyen Bao; Truong, Tuyen Ngoc

doi:10.1016/j.arabjc.2021.103682

Cited by 11 publications

(4 citation statements)

References 46 publications

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“…Furthermore, Rahman, M. et al [ 22 ] and Pham, E.C. et al [ 23 ] confirmed that ASN(A:54), PRO(A:87) and ILE(A:86) are responsible forthe formation of different interactions in the binding site of the target.…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of 2-Aminopyridine Derivatives: Antibacterial Activity Assessment and Molecular Docking Studies

et al. 2022

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A new and suitable multicomponent one-pot reaction was developed for the synthesis of 2-amino-3-cyanopyridine derivatives. Background: This synthesis was demonstrated by the efficient and easy access to a variety of substituted 2-aminopyridines using enaminones as key precursors under solvent-free conditions. Methods: A range of spectroscopic techniques was used to determine and confirm the chemical structures (FTIR, 1H NMR, 13C NMR). The antimicrobial potency of synthesized compounds (2a–d) was tested using disk diffusion assays, and the Minimum Inhibitory Concentration (MIC) for the active compounds was determined against a panel of microorganisms, including Gram-positive and Gram-negative bacteria and yeasts. Moreover, a docking analysis was conducted by Molecular Operating Environment (MOE) software to provide supplementary information about the potential, as well as an ADME-T prediction to describe the pharmacokinetic properties of the best compound and its toxicity. Results: The results of the antimicrobial activity indicated that compound 2c showed the highest activity against Gram-positive bacteria, particularly S. aureus and B. subtilis whose MIC values were 0.039 ± 0.000 µg·mL−1. The results of the theoretical study of compound 2c were in line with the experimental data and exhibited excellent antibacterial potential. Conclusions: On the basis of the obtained results, compound 2c can be used as an antibacterial agent model with high antibacterial potency.

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Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of 2-Aminopyridine Derivatives: Antibacterial Activity Assessment and Molecular Docking Studies

et al. 2022

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“…The MW-assisted synthesis of fluorinated derivatives of 1,4-disubstituted 3-methylpyrazol-5-(4H)-one and 3-methyl-1H-pyrazol-5-ol was performed by Pham et al in a three-step process. [77] Firstly, the acid catalyzed condensation of phenylhydrazines (43) and ethylacetoacetate produced the 1monosubstituted 3-methylpyrazol-5-(4H)-one derivatives (44). [78] The further condensation of these derivatives 44 with substituted benzaldehyde in acetic acid generated the 1,4-disubstituted 3-methylpyrazol-5(4H)-one derivative 45 under MW heating.…”

Section: Pyrazole and Pyrazoline Derivativesmentioning

confidence: 99%

“…The azide-alkyne cycloaddition of azide 75 with terminal alkynes (both aromatic or aliphatic) provides the N-bromotetrafluoroethyl substituted 1,2,3-triazoles (76). Further Zn/acetic acid reduction of compound 76 afforded N-tetrafluoroethyl triazoles (77). Rhodiumcatalyzed transannulation of triazoles with nitriles produces Ntetrafluoroethylated imidazoles (78).…”

Section: Imidazole Derivativesmentioning

confidence: 99%

Microwave‐Assisted Synthesis of Fluorinated 5‐Membered Nitrogen Heterocycles

Prakash,

Singh

2024

ChemistrySelect

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The fluorinated 5‐membered N‐containing heterocyclic compounds have wide utility in varied fields. The importance of these compounds has encouraged researchers to explore environment‐friendly synthetic techniques for their synthesis. In this context, microwave‐assisted synthesis has proved beneficial for the synthesis of fluorinated 5‐membered N‐heterocycles in an environmentally benign and energy‐efficient manner. Compared to conventional heating, it offers several advantages, including quick heating, short reaction times, higher yields, and fewer side reactions. This article highlights the microwave‐assisted fluorination of 5‐membered N‐heterocyclic compounds along with the synthesis of fluorinated 5‐membered N‐heterocyclic compounds using fluorinated starting materials.

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“…Earlier reports suggest that they have targeted different bacteria TMKs with different compounds. All those compounds followed Lipinski's rules (MW<350g/mol) [13,14] for the mycobacteria TMK PDB: 5NQ5 binding energy was found to be-36.75kal/mol. After docking essential amino acids for docked compound tetrahydro pyrimidinone Arg95, Arg107, Asn100 Arg75 with hydrogen bonds [15].…”

Section: Introductionmentioning

confidence: 96%

Molecular Docking Dynamics of Selected Benzylidene Amino Phenyl Acetamides as TMK Inhibitors Using High Throughput Virtual Screening (Htvs)

JAYANTHI,

AHMED,

BAQI

et al. 2024

Int J App Pharm

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Objective: Thymidylate kinase (TMK) plays a crucial role in bacterial DNA synthesis by catalyzing the phosphorylation of deoxythymidine monophosphate (dTMP) to form deoxythymidine diphosphate (dTDP). Consequently, this enzyme emerges as a promising target for developing novel antibacterial drugs. However, no antibiotics were reported for this target, especially active against Staphylococcus aureus thymidylate kinase. Methods: Benzylidene acetamide-based ligands were examined for their potency using the in silico method. These novel ligand structures were built using ChemDraw software. The protein was retrieved from the Research Collaboratory for Structural Bioinformatics Protein Data Bank (RCSB PDB) website. The molecular docking and binding free energy calculation by prime Molecular Mechanics in Generalized Bond Surface Area (MM-GBSA) was performed for selected ligands. A 100 ns molecular dynamic simulation was also performed to assess the stability of the potential ligand as TMK inhibitors. Results: All ten molecules have shown good glide scores and hydrophobic and hydrogen hydrophobic hydrogen bonding interactions with Arg48, Arg36, and π-π stacking Phe66 in the TMK enzyme (PDB: 4HLC). Among them, N-(2-ethylphenyl)-2-(4-((4-nitrobenzylidene) amino) phenoxy) acetamide molecule had high XP-docking scores of-3.27 kcal/mol based on extra-precision data. Prime Molecular Mechanics in Generalized Bond Surface Area study (MM-GBSA) studies also showed promising binding affinities that are ΔBind (-65.80), ΔLipo (-28.55), and ΔVdW (-55.10). Phe66 amino acid residue maintained continuous connections with the ligand during MD simulation. This ligand showed promising binding affinity with the SaTMK target. Conclusion: The N-(2-ethylphenyl)-2-(4-((4-nitrobenzylidene) amino) phenoxy) acetamide ligand at the position of the benzene ring displayed nitrogen and oxygen group, thus indicating good potential activity as the inhibitor of TMK to treat antibacterial agents.

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Design, synthesis, antimicrobial evaluations and in silico studies of novel pyrazol-5(4H)-one and 1H-pyrazol-5-ol derivatives

Cited by 11 publications

References 46 publications

Efficient Synthesis of 2-Aminopyridine Derivatives: Antibacterial Activity Assessment and Molecular Docking Studies

Efficient Synthesis of 2-Aminopyridine Derivatives: Antibacterial Activity Assessment and Molecular Docking Studies

Microwave‐Assisted Synthesis of Fluorinated 5‐Membered Nitrogen Heterocycles

Molecular Docking Dynamics of Selected Benzylidene Amino Phenyl Acetamides as TMK Inhibitors Using High Throughput Virtual Screening (Htvs)

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