One‐pot cascade synthesis and in vitro evaluation of anti‐inflammatory and antidiabetic activities of S‐methylphenyl substituted acridine‐1,8‐diones

Abstract

Various S-methylphenyl substituted acridine-1,8-dione series (4a-i) were synthesized through a one-pot cascade synthetic approach involving the reaction of 4-(methylthio)benzaldehyde and dimedone with a variety of amines as nitrogen source under reflux in ethanol. All the synthesized derivatives were characterized by using spectroscopic methods. In vitro evaluations of anti-inflammatory and antidiabetic efficacies of all the synthesized compounds were investigated. The anti-inflammatory results infer that the compounds 4c and 4d are showing excellent activity with an inhibition percentage of 80.58 ± 0.42, 81.72 ± 1.72 by membrane stabilization and 77.72 ± 0.76, 78.76 ± 0.81 by albumin denaturation methods, which is comparable with the standard diclofenac at a concentration of 100 μg/ml. Further, the antidiabetic assay revealed the moderate activity for the synthesized compounds at a concentration of 100 μg/ml with respect to their standard drug, acarbose.

Acridine‐1,8‐diones: Synthesis and Biological Applications

“…The anti‐inflammatory and anti‐diabetic activity of acridinediones were scrutinized by Mallu and companions [174] . Here, 4‐(methylthio)benzaldehyde was refluxed with different amines and dimedone in ethanol to obtain S‐methylphenyl substituted acridine‐1,8‐diones in moderate to good yields.…”

“…The regioselective reaction of dimedone, 7-substituted tetrazolo [1,5- The anti-inflammatory and anti-diabetic activity of acridinediones were scrutinized by Mallu and companions. [174] Here, 4- compared to reference drug, diclofenac. In-vitro anti-diabetic assay results revealed their moderate activity as compared to standard drug acarbose.…”

“…The regioselective reaction of dimedone, 7-substituted tetrazolo [1,5-a]quinoline-4-carbaldehyde, and 3,4-substituted phenylamino)-5,5-disubstituted cyclohex-2-enones (5) in acetic acid yielded a range of tetrazolo [1,5-a] The anti-inflammatory and anti-diabetic activity of acridinediones were scrutinized by Mallu and companions. [174] Here, 4-(methylthio)benzaldehyde was refluxed with different amines and dimedone in ethanol to obtain S-methylphenyl substituted acridine-1,8-diones in moderate to good yields. Among all the compounds, aniline and p-F aniline substituted derivatives demonstrated excellent membrane stabilization ( compared to reference drug, diclofenac.…”

Desenvolvimento de metodologia multicomponente, catalisada por cloreto de zirconila octaidratado, utilizando micro-ondas doméstico para síntese de acridino-1,8-dionas

“…O interesse pela síntese dessa classe de compostos vem aumentando ao longo dos anos devido as suas bioatividades, tais como antiviral (FERNANDES et al, 2021) antibacteriana (KAYA et al, 2013), citotóxica (MULAKAYALA et al, 2012), leishmanicida (NISAR et al, 2013 WANG et al, 2017), antidiabética e anti-inflamatória (MALLU et al, 2017), atividade inibitória frente à enzima fosfatase alcalina (FAISAL et al, 2018) e antimicrobiana (JOSEPHRAJAN et al, 2005). Propriedades ópticas das acridinodionas (THORAT et al 2016) e seu uso como sensor químico também são descritos na literatura (IQBAL et al, 2018).…”

“…O composto (20) (Figura 1.13) apresentou atividade anti-inflamatória (81,72% de inibição do processo inflamatório) similar ao fármaco diclofenaco (82,85%) na concentração de 100 µg mL -1 . A atividade antidiabética dos compostos, avaliada in vitro utilizando ensaios de inibição da amilase, mostrou que os compostos possuem moderada atividade antidiabética na concentração de 100 µg mL -1 (MALLU et al, 2017).…”