Synthesis, conformational studies and NBO analysis of (4-chloro-3,5-dimethyl-1H-pyrazol- 1-yl)(p-tolyl)methanone

Channar, Pervaiz Ali; Saeed, Aamer; Erben, Mauricio F.; Larik, Fayaz Ali; Riaz, Saira; Flörke, Ülrich; Arshad, Muhammad

doi:10.1016/j.molstruc.2019.04.085

Cited by 25 publications

(14 citation statements)

References 29 publications

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“…Besides, the spectra showed also the presence of absorption bands at 3220–3365 cm −1 assigned to NH groups, which confirmed the formation of the triazole rings in the thione form. These results were in agreement with those reported previously for similar compounds [39,40] …”

Section: Resultssupporting

confidence: 94%

“…The IR spectral data were in accordance with that previously reported for related compounds. [39,40] On the other hand, the bis-(1,3,4-oxadiazole-2-thione),17 was also designed and synthesized from 1,2,3-triazole bearing bis-acid hydrazide 4. Thus, thermal treatment of compound 4 with carbon disulfide in ethanolic potassium hydroxide solution yielded the desired bis-1,3,4-oxadiazole-2-thione17 in 80 % yield (Scheme 5).…”

Section: Chemistrymentioning

confidence: 99%

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Novel 1,2,3‐Triazole Derivatives as Potential Inhibitors against Covid‐19 Main Protease: Synthesis, Characterization, Molecular Docking and DFT Studies

et al. 2021

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The highly contagious nature of Covid-19 attracted us to this challenging area of research, mainly because the disease is spreading very fast and until now, no effective method of a safe treatment or a vaccine is developed. A library of novel 1,2,3-triazoles based 1,2,4-triazole, 1,3,4-oxadiazole and/or 1,3,4-thiadiazole scaffolds were designed and successfully synthesized. Different spectroscopic tools efficiently characterized all the newly synthesized hybrid molecules. An interesting finding is that some of the newly designed compounds revealed two isomeric forms. The ratio is affected by the size of the attached group as well as the type of the heteroatom forming the side ring attached to the central 1,2,3-triazole ring. The experimental spectroscopic data is in agreement with the DFT calculations at B3LYP 6-31G (d,p) with regard to the geometrical conformation of the prepared compounds. The DFT results revealed that the stability of one isomeric form over the other in the range of 0.057-0.161 Kcal mol À 1 . A docking study was performed using PyRx and AutoDockVina to investigate the activity of the prepared 1,2,3-triazoles as antiviral agents. Bond affinity scores of the 1,2,3-triazole derivatives were detected in the range of À 6.0 to À 8.8 kcal/ mol showing binding to the active sites of the 6LU7 protease and hence could be anticipated to inhibit the activity of the enzyme. Verification of the docking results was performed using the M pro alignment of coronaviruses substrate-binding pockets of COVID-19 against the ligands. As per these results, it can be proposed that the title hybrid molecules are acceptable candidates against COVID-19 for possible medicinal agents.

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Section: Resultssupporting

confidence: 94%

Section: Chemistrymentioning

confidence: 99%

Novel 1,2,3‐Triazole Derivatives as Potential Inhibitors against Covid‐19 Main Protease: Synthesis, Characterization, Molecular Docking and DFT Studies

et al. 2021

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“…The 2-thio substitution favors a strong resonance between the sulfur atom and the oxazole group, with the lpπ(S1)→ π∗(C7 = N1) interaction amounting up to 29.09 kcal/mol for the most stable conformer. Similar resonance interaction energies were reported for related heterocycles [ 22 , 23 ]. Furthermore, the π-electron system is also extended over the methoxycarbonyl group, with strong lpπ(O2)→ π∗(C=O3) of ca .…”

Section: Resultssupporting

confidence: 84%

Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles

Saeed

Shabir

Hökelek

et al. 2021

Heliyon

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Solventless cyclocondensation of 2-aminothiophenol with thiourea afforded the benzo[ d ]oxazole-2-thiol ( 3a ) capable of existing also in the tautomeric form benzo[ d ]oxazole-2(3 H )-thione ( 3b ). Acylation with methyl chloroacetate in dry ethanol in absence of any base or catalyst selectively afforded the S -substituted ester 2-(methoxycarbonylmethylthio)benzo[ d ]oxazole ( 4a ) in preference to the corresponding N -substituted ester N -(methoxycarbonylmethyl)thioxobenzoxazole ( 4b ). Quantum chemical calculations were conducted to determine the conformational landscape and NBO population analysis showed the strong electronic delocalization via resonance interactions on the 2-mercaptobenzaxazole group. The anomeric effect and the occurrence of a 1,4-S···O intramolecular interactions suggest the relevance of chalcogen bonding in the conformational preference. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (33.2%), H⋯O/O⋯H (19.9%) and H⋯C/C⋯H (17.8%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C–H⋯O hydrogen-bond energy is 44.8 kJ mol −1 .

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“…A small energy gap allows HOMO electrons to be easily excited to LUMO orbitals . Electron transfer and conjugation in the molecule were analyzed by using NBOs to understand the electronic resonance of A2 and B2 , and the degree of electron delocalization was evaluated by using the energy of the conjugation interaction …”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Activity, and Molecular Docking Studies of Novel 5‐Substituted‐1,2,4‐Triazole‐3‐thione Derivatives

et al. 2020

ChemistrySelect

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Seven Schiff base compounds were synthesized via the nucleophilic condensation of 5‐substituted‐3‐thione‐1,2,4‐triazole and 2,4,6‐trimethyl benzaldehyde. All of the synthesized compounds (A1–A3 and B1–B4) were thoroughly characterized by using spectroscopic and physical analytical methods. The in vitro antifungal activities of the prepared compounds were studied, and results showed that A2, B1, B2, and B3 have good biological activity. Molecular docking was used to predict the binding modes of the ligands to 6CR2 protein, and the reasons behind the excellent activities of A2 and B2 were explored. Finally,the highest occupied molecular orbital, lowest unoccupied molecular orbital, and natural bonding orbital of the compounds were calculated by using density functional theory at the B3LYP/6‐31G level.

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Synthesis, conformational studies and NBO analysis of (4-chloro-3,5-dimethyl-1H-pyrazol- 1-yl)(p-tolyl)methanone

Cited by 25 publications

References 29 publications

Novel 1,2,3‐Triazole Derivatives as Potential Inhibitors against Covid‐19 Main Protease: Synthesis, Characterization, Molecular Docking and DFT Studies

Novel 1,2,3‐Triazole Derivatives as Potential Inhibitors against Covid‐19 Main Protease: Synthesis, Characterization, Molecular Docking and DFT Studies

Synthesis, conformation and Hirshfeld surface analysis of benzoxazole methyl ester as a versatile building block for heterocycles

Synthesis, Biological Activity, and Molecular Docking Studies of Novel 5‐Substituted‐1,2,4‐Triazole‐3‐thione Derivatives

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