A New Insight into Non-covalent Interactions in 1,4-Disubstituted 1H-1,2,3-Triazole: Synthesis, X-ray structure, DFT calculations, in vitro Lipoxygenase Inhibition (LOX) and in silico Studies

Ahmed, Muhammad Naeem; Shabbir, Sadia; Batool, Bakhtawar; Mahmood, Tariq; Rashid, Umer; Yasin, Khawaja Ansar; Tahir, Muhammad Nawaz; Cassará, María Lucrecia Arias; Gil, Diego M.

doi:10.1016/j.molstruc.2021.130283

Cited by 15 publications

(2 citation statements)

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“…[33] Similar properties have been also described for substituted pyrazolyl thiazolyl coumarin dyes. [34][35][36] In continuance of our previous work emphasizing the significance of antiparallel displaced π-stacking [37,38] and tetrel bonding [39,40] in crystal engineering, [41] in this manuscript we report the synthesis, spectroscopic and solid state characterization of two new pyrazolyl-thiazole-coumarin hybrids that present an extended π-surface due to the planarity of the pyrazolyl-thiazole-coumarin system that mostly dictate their Xray packing (see Scheme 1). Several π-stacking modes and halogen bonding interactions have been also studied using DFT calculations and characterized by a combination of computational tools, such us molecular electrostatic potential (MEP) surfaces, the quantum theory of atoms-in-molecules and the noncovalent interaction plot (NCIPlot).…”

Section: Introductionmentioning

confidence: 78%

Synthesis and X‐ray Characterization of 4,5‐Dihydropyrazolyl‐Thiazoles Bearing a Coumarin Moiety: On the Importance of Antiparallel π‐Stacking

et al. 2022

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The synthetic protocol and solid state characterization of two new coumarin-pyrazolylthiazole hybrids (1-2) are detailed in this manuscript. Synthesized compounds were characterized applying nuclear magnetic resonance, Fourier-transform infrared spectroscopy and single-crystal X-ray diffraction techniques. A detailed structural analysis of 3- 2) is reported along with a detailed description of the noncovalent interactions and their evaluation using Hirshfeld surface analysis, emphasizing the structure-directing role of CÀ H⋅⋅⋅O, Br⋅⋅⋅π and π-π interactions. Finally, DFT energetics, molecular electrostatic potential (MEP), quantum theory of "atoms-in-molecules" (QTAIM) and noncovalent interaction plot (NCIplot) index computations have been used to further investigate the relative importance of two different π-stacking complexes observed in the solid state of both compounds, which are recurrent binding motifs in their crystal packing.

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Section: Introductionmentioning

confidence: 78%

Synthesis and X‐ray Characterization of 4,5‐Dihydropyrazolyl‐Thiazoles Bearing a Coumarin Moiety: On the Importance of Antiparallel π‐Stacking

et al. 2022

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“…Flavonoids have been reported to be efficient inhibitors for α-glucosidase as these form noncovalent interaction complexes with enzymes which bring some conformational changes and energy transfer that can be detected in common analytical techniques including fluorescent spectrometry, surface plasmon resonance, isothermal titration calorimetry, circular dichroism, etc., (He et al 2019). However, during the analysis of these changes, researchers have to face multiple barriers in experimental designs and analysis, even though most technologies have failed to quantitatively visualize the structure of the complexes formed by non-covalent interactions (Ahmed et al 2021).…”

Section: Discussionmentioning

confidence: 99%

In vitro Anti-diabetic Activity of Aqueous Methanolic Extract of Ailanthus Altissima Bark

Abid,

Amina Ramzan,

Ameen Abbas

et al. 2023

FCS

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The intestinal digestive enzyme alpha-glucosidase plays a vital role in the carbohydrate digestion. One anti-diabetic therapeutic approach reduces the postprandial glucose level by the inhibition of the alpha-glucosidase enzyme. The present study aimed to investigate the anti-diabetic activity of extract of Ailanthus altissima bark, in vitro. Three different plant extracts were formulated by using distilled water, methanol, and a mixture of methanol and water (70:30) to compare the best effect of the extract, while distilled water and metformin were used as negative and positive controls. Four different concentrations of plant extract in all solvents were used to find percentage inhibition of alpha-glucosidase. Maximum percentage inhibition was examined against 1.5 mL of all solvent extracts but aqueous methanolic plant extract showed maximum73% inhibition that was comparable to standard drug inhibition (80%). One-way ANOVA was followed for statistical analysis to find out the P-value based on which most significant and insignificant were declared. Aqueous methanolic plant extract showed the most significant results because the value of p<0.5 through the goodness of the model while aqueous plant extract showed insignificant results because the P- value is > 0.05. The assay results suggest that the presence of bioactive compounds are responsible for the versatile medicinal properties against diabetes, the aqueous methanolic extract exhibit a dose-dependent increase in inhibitory effect on alpha-glucosidase enzyme up to 73%. The current study proves aqueous methanolic extract of A. altissima bark has anti-diabetic activity in vitro and is a strong candidate for postprandial control of blood glucose level.

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A first principles study of nonlinear optical properties of a quinoline derivative

Medeiros

Valverde

Faizi

et al. 2022

Int J of Quantum Chemistry

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A quinoline derivative, 4‐(quinolin‐2‐ylmethylene)aminophenol was synthesized and structurally characterized by single crystal X‐ray diffraction. The crystal packing behavior and intermolecular interactions were examined by Hirshfeld surface analyses, 2D fingerprint plots and QTAIM analysis. The second order nonlinear response of 4‐(quinolin‐2‐ylmethylene)aminophenol molecule immersed in DMSO was investigated at PCM/DFT/CAM‐B3LYP/6–311++G(d,p) level. Theoretical calculations of the Hyper‐Rayleigh scattering (HRS) first hyperpolarizability were performed using two different procedures, the Sum‐over‐states scheme and the energy derivative method from Gaussian16. The HRS first hyperpolarizability results were compared with obtained for other organic compounds and shown that the 4‐(quinolin‐2‐ylmethylene)aminophenol presents a good nonlinear optical response.

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A New Insight into Non-covalent Interactions in 1,4-Disubstituted 1H-1,2,3-Triazole: Synthesis, X-ray structure, DFT calculations, in vitro Lipoxygenase Inhibition (LOX) and in silico Studies

Cited by 15 publications

References 37 publications

Synthesis and X‐ray Characterization of 4,5‐Dihydropyrazolyl‐Thiazoles Bearing a Coumarin Moiety: On the Importance of Antiparallel π‐Stacking

Synthesis and X‐ray Characterization of 4,5‐Dihydropyrazolyl‐Thiazoles Bearing a Coumarin Moiety: On the Importance of Antiparallel π‐Stacking

In vitro Anti-diabetic Activity of Aqueous Methanolic Extract of Ailanthus Altissima Bark

A first principles study of nonlinear optical properties of a quinoline derivative

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