X-ray characterization, Hirshfeld surface analysis, DFT calculations,<i>in vitro</i>and<i>in silico</i>lipoxygenase inhibition (LOX) studies of dichlorophenyl substituted 3-hydroxy-chromenones

Ahmed, Muhammad Naeem; Ghias, Mehreen; Shah, Syed Wadood Ali; Shoaib, Mohammad; Tahir, Muhammad Nawaz; Ashfaq, Muhammad; Andleeb, Hina; Gil, Diego M.; Frontera, Antonio

doi:10.1039/d1nj04340d

Cited by 23 publications

(8 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…HS analysis is commonly used to visualize and identify intermolecular interactions in the supramolecular structures. 59 The Hirshfeld surface was mapped with d norm using a red-blue-white color scheme, in which the red regions represented strong contacts, such as O⋯H contacts, while the blue regions indicated no significant contacts, and the white regions corresponded to weak contacts like H⋯H, Cl⋯H and C⋯H. The Hirshfeld surface of 2,4-D and the (2,4-D) + cations in multicomponent crystals are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Combined virtual and experimental screening of multicomponent crystals of 2,4-dichlorophenoxyacetic acid

et al. 2022

New J. Chem.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Combined virtual and experimental screening of multicomponent crystals of 2,4-dichlorophenoxyacetic acid

et al. 2022

New J. Chem.

View full text Add to dashboard Cite

show abstract

“…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 X‐ray 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: 66%

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

et al. 2022

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…The 2D fingerprint plot analysis is a way to elaborate on the interatomic contacts in terms of their percentage contributions in the crystal packing. , We are going to compare the important 2D fingerprint plots of PBMP with DBC (reference code LEBPAK) and BCC (reference code QQQAQG02). Figures a,e,i shows 2D plots for the overall interactions containing the contributions of all of the possible interatomic contacts for PBMP , DBC , and BCC , respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

et al. 2022

Self Cite

View full text Add to dashboard Cite

Three symmetrical bis-aryl-α,β-unsaturated ketone derivatives, 2,6-di((E)-benzylidene)-cyclohexan-1-one (DBC), 2,6bis((E)-4-chlorobenzylidene)cyclohexan-1-one (BCC), and (1E,1′E,4E,4′E)-5,5′-(1,4-phenylene)bis(2-methyl-1-phenylpenta-1,4-dien-3-one) (PBMP), have been prepared using the aldol condensation approach toward ketones having two enolizable sites. The structures of DBC, BCC, and PBMP have been resolved via spectrometric methods. Moreover, the crystal structure of PBMP is determined by the single-crystal X-ray diffraction (SC-XRD) technique, which revealed that the PBMP molecular assembly is stabilized by the intermolecular C−H•••O bonding and C− O•••π and weak T-shaped offset π•••π stacking interactions. The Hirshfeld surface analysis (HSA) of the PBMP crystal structure was performed as well, and the results were compared with the results of DBC and BCC. The density functional theory (DFT) study results revealed that the longer conjugated molecule of PBMP has smaller but still quite significant HOMO−LUMO gaps compared to the smaller molecules of BCC and DBC.The natural population analysis (NPA) and natural bonding orbital (NBO) analysis were performed. Accordingly, the hydrogen bonding and dipole−dipole interactions stabilize the crystal structures of these compounds. Additionally, the NBO analysis showed numerous high-energy stabilizing interactions for the PBMP compound due to the presence of numerous delocalized and relatively easily polarizable π-electrons, thus implying its significant thermodynamic stability. According to the global reactivity parameter (GRP) analysis, the compounds BCC and DBC are relatively stable in redox processes and have high thermodynamic stability and relatively lower reactivity in general. The molecular electrostatic potential (MEP) analysis results imply potential formation of the intermolecular hydrogen bonding and dispersion interactions, which stabilizes the crystal structures of these compounds.

show abstract

X-ray characterization, Hirshfeld surface analysis, DFT calculations,in vitroandin silicolipoxygenase inhibition (LOX) studies of dichlorophenyl substituted 3-hydroxy-chromenones

Cited by 23 publications

References 54 publications

Combined virtual and experimental screening of multicomponent crystals of 2,4-dichlorophenoxyacetic acid

Combined virtual and experimental screening of multicomponent crystals of 2,4-dichlorophenoxyacetic acid

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

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

Contact Info

Product

Resources

About