Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes

Aguilar-Llanos, Esteban; Carrera-Pacheco, Saskya E.; González-Pastor, Rebeca; Zúñiga-Miranda, Johana; Rodríguez-Pólit, Cristina; Romero-Benavides, Juan Carlos; Heredia-Moya, Jorge

doi:10.3390/ecsoc-26-13684

Cited by 1 publication

(10 citation statements)

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“…Schiff bases 3a−h (Scheme 1) were synthesized in good to excellent yield by the condensation of 4-amino-1,5-dimethyl-2phenylpyrazol-3-one (1) with various cinnamaldehydes 2a−h in ethanol, as previously reported. 29 In all cases, the synthesized compounds correspond to trans isomers around the side chain olefinic double bond (J α−β ≈ 16 Hz), with no evidence of cis isomer formation (see the Experimental Section and Supporting Information, Figures S1−S8).…”

Section: ■ Results and Discussionmentioning

confidence: 91%

“…41 Antimicrobial Activity. On the other hand, to expand on the previously reported antibacterial activity of these compounds, 29 their activity was tested against many Gram-negative bacteria, including Pseudomonas aeruginosa, Salmonella enterica, Klebsiella ozaenae, and Enterobacter gergoviae. The minimum inhibitory concentrations (MICs) are shown in Table 4.…”

Section: Crystallographic Structural Resultsmentioning

confidence: 99%

“…All Schiff bases 3 were synthesized, as previously reported. , Equimolar amounts of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (1) (1.722 mmol) and substituted cinnamaldehydes 2a – h (1.722 mmol) were dissolved in 5.0 mL of EtOH and refluxed for 1 to 24 h, except for the synthesis of 3f , which was carried out at room temperature. The progress of the reaction was monitored by TLC.…”

Section: Methodsmentioning

confidence: 99%

“…The great majority of reports on Schiff bases derived from 4-AAP have concentrated primarily on the use of substituted benzaldehydes, with relatively few reports involving the use of cinnamaldehydes. The presence of a double-bound conjugated with the imino moiety is attractive not only for the synthesis of novel compounds with potential biological activity but also for potential uses in optical applications. , We recently synthesized several Schiff base derivatives obtained from 4-AAP with various cinnamaldehydes and preliminary data show that these compounds present antibacterial activity and antiproliferative activity against several carcinoma cell lines . In order to continue our investigation of these compounds, we report here vibrational (IR), electronic (UV–vis) spectroscopy, electrochemical characterization of these Schiff base derivatives, and X-ray diffraction studies of four compounds.…”

Section: Introductionmentioning

confidence: 99%

“…27,28 We recently synthesized several Schiff base derivatives obtained from 4-AAP with various cinnamaldehydes and preliminary data show that these compounds present antibacterial activity and antiproliferative activity against several carcinoma cell lines. 29 Scheme 1. Synthesis of Schiff Base Derivatives 3a−h In order to continue our investigation of these compounds, we report here vibrational (IR), electronic (UV−vis) spectroscopy, electrochemical characterization of these Schiff base derivatives, and X-ray diffraction studies of four compounds.…”

Section: ■ Introductionmentioning

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: ■ Results and Discussionmentioning

confidence: 91%

Section: Crystallographic Structural Resultsmentioning

confidence: 99%