Synthesis, α-glucosidase inhibition and molecular docking study of coumarin based derivatives

Taha, Muhammad; Shah, Syed Adnan Ali; Afifi, Muhammad; Imran, Syahrul; Sultan, Sadia; Rahim, Fazal; Khan, Khalid Mohammed

doi:10.1016/j.bioorg.2018.01.033

Cited by 100 publications

(34 citation statements)

References 33 publications

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“…The crystal structures of target proteins were retrieved from the Research Collaboratory for Structural Bioinformatics (RCSB) Protein Data Bank ( ). Isomaltase from Saccharomyces cerevisiae co-crystallized with maltose (PDB ID: 3A4A) was used here as the α-glucosidase protein since it shows 85% similarity to yeast α-glucosidase (MAL12) through homology modeling [ 47 ]. On the other hand, acetylcholinesterase protein co-crystalized with donepezil (PDB ID: 4EY7) was used for docking calculations.…”

Section: Methodsmentioning

confidence: 99%

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Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies

et al. 2018

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Okinawa propolis (OP) and its major ingredients were reported to have anti-cancer effects and lifespan-extending effects on Caenorhabditis elegans through inactivation of the oncogenic kinase, p21-activated kinase 1 (PAK1). Herein, five prenylated flavonoids from OP, nymphaeol-A (NA), nymphaeol-B (NB), nymphaeol-C (NC), isonymphaeol-B (INB), and 3′-geranyl-naringenin (GN), were evaluated for their anti-inflammatory, anti-diabetic, and anti-Alzheimer’s effects using in vitro techniques. They showed significant anti-inflammatory effects through inhibition of albumin denaturation (half maximal inhibitory concentration (IC50) values of 0.26–1.02 µM), nitrite accumulation (IC50 values of 2.4–7.0 µM), and cyclooxygenase-2 (COX-2) activity (IC50 values of 11.74–24.03 µM). They also strongly suppressed in vitro α-glucosidase enzyme activity with IC50 values of 3.77–5.66 µM. However, only INB and NA inhibited acetylcholinesterase significantly compared to the standard drug donepezil, with IC50 values of 7.23 and 7.77 µM, respectively. Molecular docking results indicated that OP compounds have good binding affinity to the α-glucosidase and acetylcholinesterase proteins, making non-bonded interactions with their active residues and surrounding allosteric residues. In addition, none of the compounds violated Lipinski’s rule of five and showed notable toxicity parameters. Density functional theory (DFT)-based global reactivity descriptors demonstrated their high reactive nature along with the kinetic stability. In conclusion, this combined study suggests that OP components might be beneficial in the treatment of inflammation, type 2 diabetes mellitus, and Alzheimer’s disease.

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Section: Methodsmentioning

confidence: 99%

“…All compounds were fully optimized by DFT employing Becke’s three-parameter hybrid model, Lee–Yang–Parr (B3LYP) correlation functional method at the 6–31G (d,p) level, using Gaussian09 software [ 47 ]. Fully optimized structures of the compounds are shown in Figure S2 .…”

Section: Methodsmentioning

confidence: 99%

Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies

et al. 2018

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“…Coumarins are found in several plant families and essential oils and are used as fragrant additives in food and cosmetics [12]. Many reports have suggested that the coumarins possess a huge array of biological roles, such as antithrombotic, neuroprotective, antidiabetic, anticoagulant, anti-inflammatory, antioxidant, and antiplasmodial activities [13][14][15][16][17][18][19]. Due to technical advancement, the coumarins and its derivatives are becoming a potential source for new drug discovery [20].…”

Section: Introductionmentioning

confidence: 99%

(E)-N′-(1-(7-Hydroxy-2-Oxo-2H-Chromen-3-Yl) Ethylidene) Benzohydrazide, a Novel Synthesized Coumarin, Ameliorates Isoproterenol-Induced Myocardial Infarction in Rats through Attenuating Oxidative Stress, Inflammation, and Apoptosis

Feriani

Khdhiri

Tir

et al. 2020

Oxidative Medicine and Cellular Longevity

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The present study was directed to investigate the effect of precotreatment with (E)-N′-(1-(7-hydroxy-2-oxo-2H-chromen-3-yl) ethylidene) benzohydrazide (7-hyd.HC), a novel potent synthesized coumarin, on isoproterenol- (ISO-) induced myocardial infarction (MI) in rats. The hydrazone compound was characterized by IR, 1D, and 2D NMR analyses. Experimental induction of MI in rats was established by ISO (85 mg/kg/day, s.c) for two consecutive days (6th and 7th days). 7-hyd.HC or sintrom was given for 7 days prior and simultaneous to ISO injection. 7-hyd.HC offered a cardiopreventive effect by preventing heart injury marker leakage (LDH, ALT, AST, CK-MB, and cTn-I) from cardiomyocytes and normalizing cardiac function and ECG pattern, as well as improving lipid profile (TC, TG, LDL-C, and HDL-C), which were altered by ISO administration. Moreover, 7-hyd.HC precotreatment significantly mitigated the oxidative stress biomarkers, as evidenced by the decrease of lipid peroxidation and the increased level of the myocardial GSH level together with the SOD, GSH-Px, and catalase activities. 7-hyd.HC inhibited the cardiac apoptosis by upregulating the expression of Bcl-2 and downregulating the expression of Bax and caspase-3 genes. In addition, 7-hyd.HC reduced the elevated fibrinogen rate and better prevented the myocardial necrosis and improved the interstitial edema and neutrophil infiltration than sintrom. Overall, 7-hyd.HC ameliorated the severity of ISO-induced myocardial infarction through improving the oxidative status, attenuating apoptosis, and reducing fibrinogen production. The 7-hyd.HC actions could be mediated by its antioxidant, antiapoptotic, and anti-inflammatory capacities.

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“…Also, urease in soils can cause excessive volatilization of ammonia in urea fertilizer since it degrades urea too rapidly . Urease inhibition studies have been given attention by researchers in recent years; some of the urease inhibitors have been reported, such as hydroxamic acid derivatives, phosphorodiamidates, and imidazoles . Unfortunately, some urease inhibitors cannot be used in mouse experiments because of their toxicity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

Menteşe

Akyüz

Yılmaz

et al. 2018

Archiv der Pharmazie

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A new series of quinazolinone hybrid molecules containing coumarin, furan, 1,2,4triazole and 1,2,4-thiadiazole rings was designed, synthesized, and screened for their urease inhibition activities. All newly synthesized compounds showed outstanding urease inhibitory potentials with IC 50 values ranging between 1.26 ± 0.07 and 7.35 ± 0.31 μg/mL. Among the series, coumarin derivatives (10a-d) exhibited the best inhibitory effect against urease in the range of IC 50 = 1.26 ± 0.07 to 1.82 ± 0.10 μg/mL, when compared to standard urease inhibitors such as acetohydroxamic acid and thiourea (IC 50 = 21.05 ± 0.96 and 15.08 ± 0.71 μg/mL, respectively). Molecular docking studies were also performed to analyze the binding mode of compound 10b, and supported the experimental results. K E Y W O R D S coumarin, furan, molecular docking, quinazolin-4(3H)-one, thiadiazole, triazole, urease inhibition

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Synthesis, α-glucosidase inhibition and molecular docking study of coumarin based derivatives

Cited by 100 publications

References 33 publications

Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies

Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies

(E)-N′-(1-(7-Hydroxy-2-Oxo-2H-Chromen-3-Yl) Ethylidene) Benzohydrazide, a Novel Synthesized Coumarin, Ameliorates Isoproterenol-Induced Myocardial Infarction in Rats through Attenuating Oxidative Stress, Inflammation, and Apoptosis

Synthesis of some novel quinazolin‐4(3H)‐one hybrid molecules as potent urease inhibitors

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