Synthesis, molecular modeling and biological evaluation of aza-flavanones as α-glucosidase inhibitors

Abstract

An efficient acid catalyzed methodology has been employed to synthesize a variety of aza-flavanones and their α-glucosidase inhibitory activity is evaluated using acarbose, miglitol and voglibose as reference standards. Molecular modeling studies were performed for all compounds to identify the important binding modes responsible for the inhibition activity of α-glucosidase which helped find key interactions between the enzyme and the active compounds. Among all the compounds , and have shown high α-glucosidase inhibition activity compared to standard reference drugs and have been identified as promising potential antidiabetic agents. This study is the first biological evaluation of aza-flavanones as α-glucosidase inhibitors.

Study of The Potential Compound on Leaves of Syzygium samarangense as An Antibacterial to Streptococcus pneumoniae

“…There have been no reports of antibacterial activity for these compounds, but many of the compounds containing the hydrazone chain have antibacterial activity [32], and some antibacterial sources currently used in medicine are known to contain hydrazide-hydrazone moieties [33]. Valeraldehyde belongs to the flavonoid group [34]. Flavonoids are a phenolic hydroxy group that has high antioxidant activity, which has various bioactivities, including antibacterial, anti-cancer, anti-inflammatory, and boosting the immune system [35].…”

A review of the syntheses of flavanones, thioflavanones, and azaflavanones from 2'‐substituted chalcones

“…Compounds 89 were treated with 0.5 equiv of TsOH in toluene for 1-2 h at 120 C, and 2-alkyl(aryl)-2,3-dihydroquinolin-4(1H)-ones (90) were obtained by dehydration and subsequent cyclization (Scheme 39). 66…”

A Novel Approach to N‐Tf 2‐Aryl‐2,3‐Dihydroquinolin‐ 4(1H)‐ones via a Ligand‐Free Pd(II)‐Catalyzed Oxidative Aza‐Michael Cyclization

“…Flavonoids are a common class of natural products and their synthetic analogs, frequently serving as pharmaceutical agents with numerous biological activities [1] . Recently, 2‐aryl‐2,3‐dihydroquinolin‐4(1 H )‐ones which are also known as aza‐flavanones in which the N is substituted for an O in the flavanone structure, have been considered novel privileged structures found in a variety of antitumor [2] and antidiabetic [3] agents, cross‐species microRNA inhibitors, [4] and PARP inhibitors (Figure 1). [5] Furthermore, 2‐aryl‐2,3‐dihydroquinolin‐4(1 H )‐ones can be transformed into various nitrogen‐bearing heterocycles, such as tetrahydroquinoline, quinoline and quinolone, which are key motifs in active pharmaceutical ingredients [6] .…”