Synthesis of two new Schiff bases; crystal structure, Hirshfeld surface analysis, density functional theory and molecular docking

Raza, Muhammad Asam; Dege, Necmi; Doğan, Onur Erman; Ağar, Tuğgan; Sumrra, Sajjad Hussain

doi:10.1016/j.molstruc.2020.129330

Cited by 20 publications

(14 citation statements)

References 26 publications

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“…The red and blue color in shape index represented the depression and projection at the point of contact between two molecules. The flat surface patches in curvedness of both the compounds revealed the presence of planar stacking arrangement [30] …”

Section: Resultsmentioning

confidence: 95%

Experimental and Computational Validation of Structural Features and BSA Binding Tendency of 5‐Hydroxy‐5‐trifluoromethyl‐3‐arylpyrazolines**

et al. 2021

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Bovine serum albumin (BSA) serves as a model protein to explore drug‐protein interactions due to its structural similarities with Human serum albumin (HSA). In this report, the binding tendency of BSA protein with synthesized trifluoromethyl functionalized pyrazoles i. e., 5‐hydroxy‐3‐(p‐methoxyphenyl)‐5‐trifluoromethyl‐4,5‐dihydropyrazole‐1‐thiocarboxamide (2 a) and 5‐hydroxy‐3‐(p‐bromophenyl)‐5‐trifluoromethyl‐4,5‐dihydropyrazole‐1‐thiocarboxamide (2 b) was explored using spectroscopic techniques. The pyrazoles were synthesized by a one‐pot reaction and characterized with the help of single‐crystal X‐ray diffraction. The crystallographic parameters were found to be in close agreement with those evaluated computationally using density functional theory (DFT). Further, to explore the nature of interactions involved in binding, Hirshfeld surface analysis was carried out, which indicated the presence of non‐covalent interactions. Specifically, hydrogen bonding viz O−H, S−H and F−H were observed in both cases. As predicted by DFT based global reactivity descriptors, compound 2 a is chemically softer than 2 b. In silico molecular docking and molecular dynamic studies were also performed to validate the nature of binding interactions present in both cases.

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Section: Resultsmentioning

confidence: 95%

Experimental and Computational Validation of Structural Features and BSA Binding Tendency of 5‐Hydroxy‐5‐trifluoromethyl‐3‐arylpyrazolines**

et al. 2021

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“…The HS was computed over d norm range of −0.55 to 1.0 Å, the curvedness range of −0.40 to 4.0 Å and the shape index range of −0.10 to 1.0 Å. The surfaces appeared transparent to display the visualization of the molecules, over which they were mapped [ Figure 7 ].The different color schemes such as red, white and blue showed intermolecular connections with distances less than, identical to, and higher than van der Waals radii, respectively [63] . On the surface, the dark red coloration occurred about the nitrogen atom of amino group and pyridine ring along with the oxygen atom of carbonyl groups.…”

Section: Resultsmentioning

confidence: 96%

Molecular docking with SARS-CoV-2 and potential drug property of a bioactive novel Zn(II) polymer: A combined experimental and theoretical study

Nashre-ul-Islam¹,

Borah²,

Raza

et al. 2023

Polyhedron

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“…Compounds 1 and 2 were docked by Molecular Operating Environment (2016.08) software. 2 In molecular modeling two PDB files 1EVE and 1P0I, the first one for AChE (acetylocholinoesterase) and the second for BChE (butyrylcholinoesterase) enzymes, were chosen. The 2D molecule-receptor interactions were exhibited by means of MOE.…”

Section: Methodsmentioning

confidence: 99%

“…Transition metals formed various types of stable complexes with these ligands and consequently played an extensive part in the advancement of coordination chemistry. 2 The condensation process of diamines with salicylaldehyde yields imine based ligands that have [N 2 O 2 ] donor sets and are available for formation of stable coordination compounds. 3 The biological activity of salicylaldehydes and their derivatives was studied.…”

Section: Introductionmentioning

confidence: 99%

“…Imines based ligands are considered the most reliable ligands owing to the lesser efforts required for their synthesis and notable versatility. Transition metals formed various types of stable complexes with these ligands and consequently played an extensive part in the advancement of coordination chemistry . The condensation process of diamines with salicylaldehyde yields imine based ligands that have [N 2 O 2 ] donor sets and are available for formation of stable coordination compounds .…”

Section: Introductionmentioning

confidence: 99%

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Therapeutical Potential of Imines; Synthesis, Single Crystal Structure, Computational, Molecular Modeling, and ADMET Evaluation

et al. 2022

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Imines are multipurpose pharmacophores, simply accessible compounds, and have a broad range of usage in several areas of chemistry especially in medicine. Two novel compound imines, ( E )-4-methyl-2-(( o -tolylimino)methyl)phenol ( 1 ) and ( E )-2-(((4-methoxybenzyl)imino)methyl)-4-methylphenol ( 2 ), were synthesized with effective product via reported protocol in the literature. Single crystal X-ray diffraction (SCXRD) was employed for structural exposition, disclosing that both compounds are orthorhombic. To optimize the newly designed imines, a B3LYP functional with a basis set 6-31G(d,p) was mainly considered. DFT results were utilized to check correlation between the data recovered from SCXRD outcomes and also to measure the energy difference. Hirshfeld surface study was done to demonstrate the intermolecular contacts along the percentage of interaction in the overall crystalline compound. Molecular operating environment program was tested against AChE and BChE enzymes to perform a modeling study of the compounds. The docking score and binding affinity of the compounds revealed that 2 showed comparatively more inhibition than 1 . In silico ADMET studies exposed the physiochemical nature of these novel compounds, and it also unveiled that both compounds behaved as drug-like candidates.

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Synthesis of two new Schiff bases; crystal structure, Hirshfeld surface analysis, density functional theory and molecular docking

Cited by 20 publications

References 26 publications

Experimental and Computational Validation of Structural Features and BSA Binding Tendency of 5‐Hydroxy‐5‐trifluoromethyl‐3‐arylpyrazolines**

Experimental and Computational Validation of Structural Features and BSA Binding Tendency of 5‐Hydroxy‐5‐trifluoromethyl‐3‐arylpyrazolines**

Molecular docking with SARS-CoV-2 and potential drug property of a bioactive novel Zn(II) polymer: A combined experimental and theoretical study

Therapeutical Potential of Imines; Synthesis, Single Crystal Structure, Computational, Molecular Modeling, and ADMET Evaluation

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