Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Obasi, Lawrence Nnamdi; Kaior, G.U.; Rhyman, Lydia; Alswaidan, Ibrahim A.; Fun, Hoong‐Kun; Ramasami, Ponnadurai

doi:10.1016/j.molstruc.2016.05.037

Cited by 24 publications

(6 citation statements)

References 27 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%

“…Strong absorption bands at 1643 cm −1 (3a−3d), 1744 cm −1 (3e), 1645 cm −1 (3f), 1641 cm −1 (3g), and 1646 cm −1 (3h), are attributed to the carbonyl of the pyrazole ring, as previously reported for related molecules. 37,38 The shift of the C�O band toward lower frequencies in the IR spectra could be explained by the short intermolecular interactions C sp2 −O•••H−C sp3 observed in the supramolecular features in the crystalline structures of 3b, 3d, 3g, and 3h. The stretching C�C of the pyrazole group appears as medium absorption bands at 1558, 1557, 1579, 1564, 1640, 1591, 1588, and 1568 cm −1 , while the weak and medium absorption bands at 1455, 1428, 1435, 1407, 1509, 1492, 1418, and 1410 cm −1 were attributed to stretching C−N.…”

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: Crystallographic Structural Resultsmentioning

confidence: 99%

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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“…Other derivatives have also been used to improve solar cell efficiency (Ismail et al, 2020). Various 4-AAP derivatives have several biological applications and 4-AAP Schiff bases from the condensation with para-methoxycinnamaldehyde display antimicrobial activity against a large spectrum of microorganisms (Obasi et al, 2016). Still more 4-AAP derivatives show DNA binding and cleavage activity has also been reported (Rosenberg et al, 1969).…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis and structure of 4-{[(E)-(7-methoxy-1,3-benzodioxol-5-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Arderne¹,

Fotsing²,

Ndinteh³

2021

Acta Cryst E

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In the title compound, C20H19N3O4, the dihedral angles between the central pyrazole ring and the pendant phenyl and substituted benzene rings are 50.95 (8) and 3.25 (12)°, respectively, and an intramolecular C—H...O link generates an S(6) ring. The benzodioxolyl ring adopts a shallow envelope conformation with the methylene C atom as the flap. In the crystal, the molecules are linked by non-classical C—H...O interactions, which generate a three-dimensional network. Solvent-accessible voids run down the c-axis direction and the residual electron density in these voids was modelled during the refinement process using the SQUEEZE algorithm [Spek (2015). Acta Cryst. C71, 9–18] within the structural checking program PLATON.

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“…Schiff bases display strong chelating ability due to the presence of unpaired electrons on nitrogen atom of the azomethine moiety, especially when one or more donor atoms located in close neighbourhood to the azomethine group. Schiff bases become interesting ligands for coordination chemistry by their chelating ability together with the convenience of separation and flexibility in changing the structural formation about the C =N group [22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation of antioxidant-antibacterial activities and computational studies of novel anthracene- and pyrene-based Schiff base derivatives

2020

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Schiff base derivatives with anthracene- and pyrene-based units, A1-A6 and P1-P6 were synthesized (89%–99% yields). Schiff base derivatives were designed to possess an heterocyclic moiety on one side to enhance the coordination ability towards metals. To investigate the biological assay of the newly synthesized compounds, their DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, metal chelating, reducing power, antibacterial and DNA binding activities were tested. A6 (63.1%) showed the maximum free radical scavenging activity among all. However, compound P3 at concentration of 200 μg/mL possessed the highest metal chelating (45.8%) activity and power of reduction. In addition, P3 and A6 showed antibacterial activity against all bacteria tested and both compounds were very well bound to CT-DNA. Density functional theory method with B3LYP/6-311++G(d,p) basis set was performed to get information about the structural and electronic properties of the present compounds. In addition, the metal coordination properties of the dimers of the parent Schiff bases were investigated through interactions with Zn 2+ .

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Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Cited by 24 publications

References 27 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

Synthesis and structure of 4-{[(E)-(7-methoxy-1,3-benzodioxol-5-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Synthesis, biological evaluation of antioxidant-antibacterial activities and computational studies of novel anthracene- and pyrene-based Schiff base derivatives

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