An investigation of supramolecular synthons in 1,2,4-triazole-3(4H)-thione compounds. X-ray crystal structures, energetic and Hirshfeld surface analysis

Saeed, Aamer; Ashraf, Zaman; Nadeem, Humaira; Pérez, Hiram; Erben, Mauricio F.

doi:10.1016/j.molstruc.2019.06.049

Cited by 31 publications

(19 citation statements)

References 61 publications

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“…The total intermolecular energy (E tot ) is the sum of electrostatic (E ele ), polarization (E pol ), dispersion (E dis ) and exchange-repulsion (E rep ) energies [ 41 ] with scale factors of 1.057, 0.740, 0.871 and 0.618, respectively. Hydrogen-bonding interaction energies (in kJ mol −1 ) are -17.6 (E ele ), -3.1 (E pol ), -62.3 (E dis ), 49.0 (E rep ) and -44.8 (E tot ) for C4–H4A···O3 = O, values that are in the expected range when comparing with reported interaction energy for related compounds [ 42 , 43 ].…”

Section: Resultsmentioning

confidence: 66%

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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Section: Resultsmentioning

confidence: 66%

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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“…Single‐crystal X‐ray analysis showed that A3 (C 15 H 20 N 4 S) crystallizes in the monoclinic space group P 2 1 / c . The molecular structure and atomic number of the compound are provided in Figure , and its geometric parameters are listed in Table …”

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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“…In fact, various conformations are likely depending on the mutual orientations of the thiadiazole groups with respect to the triazole ring. [31] Experimentally, the size of the attached substituents plays an important role to favor the predominance of one conformer over the other form. This is due to the degree of steric hindrance of the attached group on aromatic rings.…”

Section: Dft Molecular Structurementioning

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 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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An investigation of supramolecular synthons in 1,2,4-triazole-3(4H)-thione compounds. X-ray crystal structures, energetic and Hirshfeld surface analysis

Cited by 31 publications

References 61 publications

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

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

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

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