Molecular structure, DFT studies, Hirshfeld surface analysis, energy frameworks, and molecular docking studies of novel (E)-1-(4-chlorophenyl)-5-methyl-N′-((3-methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl) methylene)-1H-1, 2, 3-triazole-4-carbohydrazide

Bhola, Yogesh O.; Socha, Bhavesh N.; Pandya, Sachin B.; Dubey, Rajni; Patel, Maheshkumar K.

doi:10.1080/15421406.2020.1721946

Cited by 24 publications

(4 citation statements)

References 25 publications

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“…The Crystal Explorer 17.5 software [ 47 , 48 ] was used for the conduction of HS analysis and for the determination of intermolecular interactions. From the nearest nucleus, the HS distances d i and d e were determined, and D norm was used to estimate the normal contact distance, which was illustrated by the colors red, white, and blue.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Mustafa,

Channar,

Ejaz

et al. 2023

BMC Chemistry

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A new compound, C23H20BrN3OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å3. The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R22(14) and R22(16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.

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Section: Methodsmentioning

confidence: 99%

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Mustafa,

Channar,

Ejaz

et al. 2023

BMC Chemistry

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“…Hirshfeld surface (HS) analysis is the most effective method for determining crystal structure interactions ( Ashfaq et al, 2021 ). Using Crystal Explorer 17.5 ( Bhola et al, 2019 ), the intermolecular interactions of the crystal structure of the subject molecule were seen. On the interior and exterior of the surface, the Hirshfeld surface distance from the nearest nucleus was measured and represented by D i and D e , respectively, while D norm was used to denote the normal contact distance.…”

Section: Methodsmentioning

confidence: 99%

Facile synthesis, crystal structure, biological evaluation, and molecular modeling studies of N-((4-acetyl phenyl) carbamothioyl) pivalamide as the multitarget-directed ligand

et al. 2022

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The crystal structure of N-((4-acetylphenyl)carbamothioyl)pivalamide (3) was synthesized by inert refluxing pivaloyl isothiocyanate (2) and 4-aminoacetophenone in dry acetone. The spectroscopic characterization (1H-NMR, 13CNMR, FT-IR) and single crystal assays determined the structure of synthesized compound (3). Systematic experimental and theoretical studies were conducted to determine the molecular characteristics of the synthesized crystal. The biological examination of (3) was conducted against a variety of enzymes i.e., acetyl cholinesterase (AChE), butyl cholinesterase (BChE), alpha amylase, and urease enzyme were evaluated. The crystal exhibited approximately 85% enzyme inhibition activity against BChE and AChE, but only 73.8 % and 57.9% inhibition activity against urease and alpha amylase was observed respectively. The theoretical calculations were conducted using density functional theory studies (DFTs) with the 6–31G (d, p) basis set and B3LYP functional correlation. The Frontier molecular orbital analysis revealed that the HOMO/LUMO energy gap was smaller, which corresponds to the molecule’s reactivity. In terms of reactivity, the chemical softness value was found to be in good agreement with experimental values. In Crystal structure analysis, the intramolecular N—H•••O hydrogen bond generates a S 6) ring motif and N—H•••O interactions exist in crystal structure between the centroids of neighboring parallel aromatic (C4-C9) rings with a centroid to centroid distance of 3.9766 (7)Å. These intermolecular interactions were useful in structural stabilization. The Hirshfeld surfaces and their related two-dimensional fingerprint plots were used for thorough investigation of intermolecular interactions. According to Hirshfeld surface analysis of the crystal structure the most substantial contributions to the crystal packing are from H ••• O and H ••• N/N ••• H interactions. Molecular docking studies were conducted to evaluate the binding orientation of synthesized crystal with multiple targets. The compound exhibited stronger interactions with AChE and BChE with binding energies of -7.5 and -7.6 kcal/mol, respectively. On the basis of in-vitro and in-silico findings, it is deduced that N-((4-acetylphenyl)carbamothioyl)pivalamide 3) possesses reactive and potent multiple target inhibitory properties.

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“…This intercalation is one of the most important interactions substantial to DNA-binding mechanisms, which may be related to some of the compound's biological activity. 27,68,69…”

Section: Hirshfeld Surface (Hs) Analysismentioning

confidence: 99%

Experimental and theoretical studies on (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone: Structural, electrochemical, spectroscopic features, solid-state interactions, molecular docking and adsorption studies onto 2D carbon nanomaterials

Thaçi,

Reka,

Ristovska

et al. 2023

Maced. J. Chem. Chem. Eng.

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A monocarbonyl analog of curcumin, (2E,5E)-2,5-bis(2-methoxybenzylidene)-cyclopentanone (B2MBCP), was prepared and characterized via spectroscopic methods (NMR, UV-Vis, FT-IR, and MS). Furthermore, density functional calculations were implemented to study the molecular structure and spectroscopic features, as well as adsorption properties. In addition, Hirshfeld surface and NBO theoretical analysis were carried out. The reduced density gradient (RDG) analysis via non-covalent interactions (NCI) and interaction region indicator (IRI) indicate the presence of extensive Van der Waals interactions. These interactions are classified in different contributions and energy stabilization from Hirshfeld surface analysis where the dominant type of contacts are H···H contacts. The molecular docking studies of B2MBCP with DNA revealed cooperative interactions that led to intercalation. The results from the cyclic voltammetry (CV) measurements agreed with the calculated energies of the frontier orbitals and the compound structure. Theoretical studies indicated that the relatively flat B2MBCP is adsorbed onto a graphene surface, with a significant adsorption energy of –41.19 kcal/mol. The results of this study provide a better overall picture of the properties of MAC with a cyclopentanone core and can be taken as a useful guide in the search for new biologically active compounds and new possible means of delivery.

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Molecular structure, DFT studies, Hirshfeld surface analysis, energy frameworks, and molecular docking studies of novel (E)-1-(4-chlorophenyl)-5-methyl-N′-((3-methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl) methylene)-1H-1, 2, 3-triazole-4-carbohydrazide

Cited by 24 publications

References 25 publications

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Facile synthesis, crystal structure, biological evaluation, and molecular modeling studies of N-((4-acetyl phenyl) carbamothioyl) pivalamide as the multitarget-directed ligand

Experimental and theoretical studies on (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone: Structural, electrochemical, spectroscopic features, solid-state interactions, molecular docking and adsorption studies onto 2D carbon nanomaterials

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