Synthesis of Flavones From 2-Hydroxy Acetophenone and Aromatic Aldehyde Derivatives by Conventional Methods and Green Chemistry Approach (2024)

Order By:

Relevance

“…The spectral data of previously reported 2′-hydroxychalcones (1a–1q) are given in the following reference articles 1a, 1e , 1g, 1j , 1b , 1c , 1d , 1f , 1h , 1i , 1k , 1l , 1m , 1n , 1o , 1p and 1q . The spectral data of all the synthesized pyrazolines ( 2a–2q) are given here:…”

confidence: 99%

et al. 2022

In the present work, a concise library of 1,3,5triaryl-2-pyrazolines (2a−2q) was designed and synthesized by employing a multistep strategy, and the newly synthesized compounds were screened for their urease and α-glucosidase inhibitory activities. The compounds (2a−2q) were characterized using a combination of several spectroscopic techniques including FT-IR, 1 H NMR, 13 C NMR, and EI-MS. All the synthesized compounds, except compound 2i, were potent against urease as compared to the standard inhibitor thiourea (IC 50 = 21.37 ± 0.26 μM). These analogs disclosed varying degrees of urease inhibitory activities ranging from 9.13 ± 0.25 to 18.42 ± 0.42 μM. Compounds 2b, 2g, 2m, and 2q having IC 50 values of 9.36 ± 0.27, 9.13 ± 0.25, 9.18 ± 0.35, and 9.35 ± 0.35 μM, respectively, showed excellent inhibitory activity as compared to standard thiourea (IC 50 = 21.37 ± 0.26 μM). A kinetic study of compound 2g revealed that compound 2g inhibited urease in a competitive mode. Among the synthesized pyrazolines, the compounds 2c, 2k, 2m, and 2o exhibited excellent α-glucosidase inhibitory activity with the lowest IC 50 values of 212.52 ± 1.31, 237.26 ± 1.28, 138.35 ± 1.32, and 114.57 ± 1.35 μM, respectively, as compared to the standard acarbose (IC 50 = 375.82 ± 1.76 μM). The compounds (2a− 2q) showed α-glucosidase IC 50 values in the range of 114.57 ± 1.35 to 462.94 ± 1.23 μM. Structure−activity relationship revealed that the size and electron-donating or -withdrawing effects of substituents influenced the activities, which led to the urease and αglucosidase inhibiting properties. Compound 2m was a dual potent inhibitor against urease and α-glucosidase due to the presence of 2-CF 3 electron-withdrawing functionality on the phenyl ring. To the best of our knowledge, these synthetic compounds were found to be the most potent dual inhibitors of urease and α-glucosidase with minimum IC 50 values. The cytotoxicity of the compounds (2a−2q) was also investigated against human cell lines MCF-7 and HeLa. Compound 2l showed moderate cytotoxic activity against MCF-7 and HeLa cell lines. Moreover, in silico studies on most active compounds were also performed to understand the binding interaction of most active compounds with active sites of urease and α-glucosidase enzymes. Some compounds exhibited drug-like characteristics due to their lower cytotoxic and good ADME profiles.

In this research, Chalcone (M1-10) was prepared by reaction of aromatic aldehydes with substituted acetophenone, through reaction of Chalcone with Malononitrile in an acidic medium, where pyridine compounds (M19-26) were obtained. The bioactivity of the prepared compounds was tested against Gram-negative and Gram-positive bacteria (Klebsellia pneumonia, Pseudomnas putida, Staph aureus, Enterococcus faecalis). the lowest inhibitory concentration compared to (Ciprofloxacin) and the prepared compounds were diagnosed by physical spectrophotometric methods using spectrophotometers. I.R, 1H-NMR, 13C-NMR.

Flavone compounds present as secondary metabolites in many plants have beneficial phytochemical activity. Isolation of flavones from various parts of plants has been widely carried out, but the synthesis pathway is another way to obtain higher yields. This research aimed to synthesize flavone compounds from vanillin and 2-hydroxyacetophenone through chalcone intermediates to produce a 74% yield using an iodide catalyst. This new flavone compound has been used as a chemosensor to detect anions