Preparation, QTAIM and Single‐Crystal Exploration of the Pyrimethamine‐Based Co‐Crystal Salts with Substituted Benzoic Acids

Ali, Akbar; Khalid, Muhammad; Ashfaq, Muhammad; Malik, Abida Naseem; Tahir, Muhammad Nawaz; Assiri, Mohammed A.; Imran, Muhammad; Morais, Sara Figueirêdo de Alcântara; Braga, Ataualpa Albert Carmo

doi:10.1002/slct.202200349

Cited by 17 publications

(9 citation statements)

References 36 publications

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“…On the HS, the short and long connections are represented by red and blue patches, respectively. The white dots on the HS indicate the connections where the distance between the interacting atoms is smaller than the total of the atoms’ van der Waals radii. − Figure a,b shows the HS over d norm for Cu-NTA and Cu-DNTA , respectively. The red spot on the HS of Cu-NTA near carboxylate O-atoms, water molecules, and ortho CH of the benzene ring indicates that these atoms are involved in the H-bonding interactions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Crystal Structures, and Supramolecular Assembly of Copper Complexes Derived from Nitroterephthalic Acid along with Hirshfeld Surface Analysis and Quantum Chemical Studies

et al. 2023

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Two new Cu(II) carboxylate complexes, Cu-NTA and Cu-DNTA, were prepared by treating 2-nitroterephthalic acid with CuSO4·5H2O at room temperature. The synthesized complexes were characterized by elemental (CHN), FT-IR, and thermogravimetric analysis. The crystal structures of both complexes were explored by single crystal X-ray diffraction analysis, which inferred that the coordination geometry is slightly distorted octahedral and square pyramidal in Cu-NTA and Cu-DNTA, respectively. The non-covalent interactions that are the main feature of the supramolecular assembly were investigated by Hirshfeld surface analysis for both complexes. The propensity of each pair of chemical moieties involved in crystal-packing interactions was determined by the enrichment ratio. Quantum chemical computations were performed to optimize the molecular geometry of complex Cu-NTA and compared it with the experimental single crystal structure, which was found to be in sensible agreement with the experimental structure of the complex. The DFT method was used to see the potential of the selected Cu-NTA complex for linear and nonlinear optical properties. The static NLO polarizability <γ> of complex Cu-NTA was calculated to be 86.28 × 10–36 esu at M06 functional and 6-31G*/LANL2DZ basis set, which was rationally large to look for NLO applications of complex Cu-NTA. Additionally, the molecular electrostatic potential and frontier molecular orbitals were also computed with the same methodology to see electronic characteristics and ground-state electronic charge distributions.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Crystal Structures, and Supramolecular Assembly of Copper Complexes Derived from Nitroterephthalic Acid along with Hirshfeld Surface Analysis and Quantum Chemical Studies

et al. 2023

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“…The enrichment ratio provides the actual contacts for a given single crystal [ 40 , 41 ]. The enrichment ratio is determined as a result of the division of the actual contact value obtained directly from CrystalExplorer by the ratio of the random contact determined theoretically.…”

Section: Resultsmentioning

confidence: 99%

Exploring Probenecid Derived 1,3,4-Oxadiazole-Phthalimide Hybrid as α-Amylase Inhibitor: Synthesis, Structural Investigation, and Molecular Modeling

et al. 2023

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1,3,4-Oxadiazole moiety is a crucial pharmacophore in many biologically active compounds. In a typical synthesis, probenecid was subjected to a sequence of reactions to obtain a 1,3,4-oxadiazole–phthalimide hybrid (PESMP) in high yields. The NMR (1H and 13C) spectroscopic analysis initially confirmed the structure of PESMP. Further spectral aspects were validated based on a single-crystal XRD analysis. Experimental findings were confirmed afterwards by executing a Hirshfeld surface (HS) analysis and quantum mechanical computations. The HS analysis showed the role of the ππ stacking interactions in PESMP. PESMP was found to have a high stability and lower reactivity in terms of global reactivity parameters. α-Amylase inhibition studies revealed that the PESMP was a good inhibitor of α-amylase with an s value of 10.60 ± 0.16 μg/mL compared with that of standard acarbose (IC50 = 8.80 ± 0.21 μg/mL). Molecular docking was also utilized to reveal the binding pose and features of PESMP against the α-amylase enzyme. Via docking computations, the high potency of PESMP and acarbose towards the α-amylase enzyme was unveiled and confirmed by docking scores of −7.4 and −9.4 kcal/mol, respectively. These findings shine a new light on the potential of PESMP compounds as α-amylase inhibitors.

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“…The QTAIM (Quantum Theory of Atoms in Molecules) analysis is a tool used in computational chemistry to analyze the electronic structure of molecules. The QTAIM analysis is a method that allows the study of the topology of the electron density in a molecule and interaction within the molecule including hydrogen and noncovalent interactions. − It provides information about the nature of the chemical bonds, the distribution of the electronic charge, and the geometry of the molecule. The definition of the critical points (CPs) of the electron density, which are locations where the gradient of the electron density is zero, serves as the foundation for the QTAIM analysis.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic, Biological, and Topological Insights on Lemonol as a Potential Anticancer Agent

et al. 2023

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A monoterpene alcohol known as lemonol was investigated experimentally as well as theoretically in order to gain insights into its geometrical structure, vibrational frequencies, solvent effects on electronic properties, molecular electrostatic potential, Mulliken atomic charge distribution, natural bond orbital, and Nonlinear Optical properties. The frontier molecular orbital energy gap values of 5.9084 eV (gas), 5.9261 eV (ethanol), 5.9185 eV (chloroform), 5.9253 eV (acetone), and 5.9176 eV (diethyl ether) were predicted, and it shows the kinetic stability and chemical reactivity of lemonol. Topological studies were conducted using Multiwfn software to understand the binding sites and weak interactions in lemonol. The antiproliferative effect of lemonol against the breast cancer cell line Michigan Cancer Foundation (MCF-7) was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, while nuclear damage, condensation, and reactive oxygen species generation were identified using acridine orange/ethidium bromide, propidium iodide, and dichlorodihydrofluorescein diacetate staining. The theoretical and experimental findings are highly correlated, confirming the structure, and the results of in vitro studies suggest that lemonol acts as a potent inhibitor against the human breast cancer cell line MCF-7, highlighting its strong antiproliferative activity.

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Preparation, QTAIM and Single‐Crystal Exploration of the Pyrimethamine‐Based Co‐Crystal Salts with Substituted Benzoic Acids

Cited by 17 publications

References 36 publications

Synthesis, Characterization, Crystal Structures, and Supramolecular Assembly of Copper Complexes Derived from Nitroterephthalic Acid along with Hirshfeld Surface Analysis and Quantum Chemical Studies

Synthesis, Characterization, Crystal Structures, and Supramolecular Assembly of Copper Complexes Derived from Nitroterephthalic Acid along with Hirshfeld Surface Analysis and Quantum Chemical Studies

Exploring Probenecid Derived 1,3,4-Oxadiazole-Phthalimide Hybrid as α-Amylase Inhibitor: Synthesis, Structural Investigation, and Molecular Modeling

Spectroscopic, Biological, and Topological Insights on Lemonol as a Potential Anticancer Agent

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