Hirshfeld Surface analysis, spectroscopic, biological studies and molecular docking of (4E)-4-((naphthalen-2-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one

Eltayeb, Naser Eltaher; Şen, Fatih; Lasri, Jamal; Hussien, Mostafa A.; Elsilk, Sobhy E.; Babgi, Bandar A.; Gökçe, Halil; Sert, Yusuf

doi:10.1016/j.molstruc.2019.127315

Cited by 19 publications

(8 citation statements)

References 54 publications

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“…Finally, stretching N–N is assigned to weak absorption bands at 1447, 1413, 1413, 1368, 1468, 1483, 1417, 1387, and 1420 cm –1 . All these characteristic absorption bands for the pyrazole group are in good agreement with related compounds. − …”

Section: Resultssupporting

confidence: 77%

“…The vibration corresponding to the azomethine –CHN group characterizes the Shiff base. The CN stretching vibrational mode was attributed to the weak absorption bands at 1587, 1592, 1594, 1600, 1655, 1608, 1618, and 1612 cm –1 , for 3a – 3h , analogous to the weak absorption bands reported for similar compounds. , …”

Section: Resultssupporting

confidence: 58%

“…The C�N stretching vibrational mode was attributed to the weak absorption bands at 1587, 1592, 1594, 1600, 1655, 1608, 1618, and 1612 cm −1 , for 3a−3h, analogous to the weak absorption bands reported for similar compounds. 39,40 On the other hand, the IR spectra of 3b−3e and 3h showed distinctive absorption bands for all different substituents of the benzyl moiety. For 3b and 3h, the −NO 2 group exhibited significant absorption bands at 1569 cm −1 and 1594 m −1 , respectively, attributed to a stretching vibrational mode.…”

Section: Crystallographic Structural Resultsmentioning

confidence: 99%

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Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Aguilar-Llanos,

Carrera-Pacheco,

González-Pastor

et al. 2023

ACS Omega

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Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet–vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound’s molecular properties, UV–vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C–N and C–C σ-bonds. Furthermore, as a result of extended bonding, the > CN– azomethine group-containing Cpyr–N(CH)–(CR)(CH)–Cbz chain (with RH for 3b, 3d, and 3h, and RCH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C–H···O and C–H···N hydrogen bonds, π···π stacking, and C–H···π and CO···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations.

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Section: Resultssupporting

confidence: 77%

Section: Resultssupporting

confidence: 58%

Section: Crystallographic Structural Resultsmentioning

confidence: 99%

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Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Aguilar-Llanos,

Carrera-Pacheco,

González-Pastor

et al. 2023

ACS Omega

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“…Hirshfeld surfaces and fingerprint plots were mapped with Crystal Explorer 3.1 software [ 21 ]. The analysis was visualized by the normalized contact distance (d norm ), which was obtained using a high surface resolution with a static color scale of -0.222 (red) to 1.274 Å (blue) and computed with the following Eq 1 ; Where d e is the distance from the Hirshfeld surface to the nearest nucleus outside the surface, d i is the corresponding distance to the nearest nucleus inside the surface, and r vdw is the van der Waals radius of the atom [ 22 ]. The d norm parameter exhibits a surface with a red-white blue color scheme [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

“…Where d e is the distance from the Hirshfeld surface to the nearest nucleus outside the surface, d i is the corresponding distance to the nearest nucleus inside the surface, and r vdw is the van der Waals radius of the atom [22]. The d norm parameter exhibits a surface with a red-white blue color scheme [23].…”

Section: Plos Onementioning

confidence: 99%

Single crystal, Hirshfeld surface and theoretical analysis of methyl 4-hydroxybenzoate, a common cosmetic, drug and food preservative—Experiment versus theory

et al. 2020

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Methyl 4-hydroxybenzoate, commonly known as methyl paraben, is an anti-microbial agent used in cosmetics and personal-care products, and as a food preservative. In this study, the single crystal X-ray structure of methyl 4-hydroxybenzoate was determined at 120 K. The crystal structure comprises three methyl 4-hydroxybenzoate molecules condensed to a 3D framework via extensive intermolecular hydrogen bonding. Hirshfeld surface analysis was performed to determine the intermolecular interactions and the crystal packing. In addition, computational calculations of methyl 4-hydroxybenzoate were obtained using the Gaussian 09W program, and by quantum mechanical methods, Hartree Fock (HF) and Density Functional Theory (DFT) with the 6-311G(d,p) basis set. The experimental FT-IR spectrum strongly correlated with the computed vibrational spectra (R 2 = 0.995). The energies of the frontier orbitals, HOMO and LUMO, were used to calculate the chemical quantum parameters. The lower band gap value (ΔE) indicates the molecular determinants underlying the known pharmaceutical activity of the molecule.

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The role of the arylidene linkage on the antimicrobial enhancement of new tert-butylcyclohexanone-based polyketones

et al. 2020

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Hirshfeld Surface analysis, spectroscopic, biological studies and molecular docking of (4E)-4-((naphthalen-2-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one

Cited by 19 publications

References 54 publications

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Single crystal, Hirshfeld surface and theoretical analysis of methyl 4-hydroxybenzoate, a common cosmetic, drug and food preservative—Experiment versus theory

The role of the arylidene linkage on the antimicrobial enhancement of new tert-butylcyclohexanone-based polyketones

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