Synthesis, spectroscopic characterization, single crystal, theoretical investigation, and biological screenings of azo-based moieties

Malik, Humera; Akhter, Zareen; Shahbaz, Muhammad Saquib; Yousuf, Sammer; Munawar, Khurram Shahzad; Muhammad, Shabbir; Qamar, Samina; Abbas, Anees; Ashfaq, Muhammad; Ahmad, Tauqeer

doi:10.1016/j.molstruc.2022.133867

Cited by 14 publications

(3 citation statements)

References 45 publications

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“…The HS plotted over d norm provides the exploration of H-bonding interactions by assigning a different color for short and long contacts. Short contacts are the representatives of 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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“…A Hirshfeld surface (HS) analysis is an informative technique to elaborate and recognize non-covalent interactions in single crystals. It was developed to divide crystal densities into molecular fragments [ 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. The hydrogen bonding interactions can be elucidated using HS plots over the normalized distance ( d norm ) property.…”

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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“…Azo group N=N contributes in the brilliant color of its compounds in vis-area in addition to its sensitivity toward pH changes which can be strong reason of their usage as colorant for tissues and indications in analytical chemistry [1][2][3][4] . Azo compounds display geometrical isomerism when exposed to light, trans-isomers are stable and converts into cis-isomer when exposed to light.…”

Section: Introductionmentioning

confidence: 99%

تحضير ، تشخيص ، دراسة التحلل الحراري و فعالية مضادات الاكسدة لمعقدات بعض ايونات معادن الكروم الثلاثي والحديد الثلاثي والمنغنيزالثنائي والبلاديوم الثنائي مع صبغة ازو مشتقة من بارا- مثل-2-هيدروكسي بنزلديهايد

Abdulrazzaq,

Al-Hamdani

2024

Baghdad Sci.J

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A new Azo Dye ligand HL was 4-((3-formyl-2-hydroxyphenyl)diazenyl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide,this synthesized ligand was used for complexation with different metal ions like Cr(III), Fe(III), Mn(II) and Pd(II) by using a molar ratio of ligand: metalas 1:1. Resulted compounds were characterized by NMR (1H and 13C), UV–vis spectroscopy, TGA, DSC, FT‐IR, MS, elemental analysis, magnetic moment and molar conductivity studies. The results showed that the geometrical structural were octahedral geometries for the Cr(III), Mn(II) and Fe(III) complexes, square planer for Pd(II) complex. The antioxidant activities of the prepared compounds were assessed by using 1.1‐diphenyl‐2‐picrylhydrazyl as the free radical, and the results showed that the complex azo dye were found to possess potent antioxidant activity. The structure–activity relationship of the ligand and its complexes indicates that the presence of electron‐donating moieties, such as Cr(III), Mn(II) and Fe(III), in the chemical structure increases the antioxidant activity, whereas the Pd(II) complexes diminished the antioxidant activity, indicating the superior activity of the hydroxyl radical (OH·) over the superoxide radical.

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Synthesis, spectroscopic characterization, single crystal, theoretical investigation, and biological screenings of azo-based moieties

Cited by 14 publications

References 45 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

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