Coumarin-chalcone hybrids targeting insulin receptor: Design, synthesis, anti-diabetic activity, and molecular docking

Coumarin-Chalcone Hybrids as Inhibitors of MAO-B: Biological Activity and In Silico Studies

“…These protons present signals corresponding to two doublets with variable δ between 8.5 and 7.0 and with J ab = 16 Hz on average. this high constant corresponds to a trans isomer [ 27 , 28 , 29 ]. As for the 13 C-NMR spectrum, we will mention typical signals such as carbonyl shifts.…”

“…As for the 13 C-NMR spectrum, we will mention typical signals such as carbonyl shifts. first of all, we will detail that the carbon of the α,β-unsaturated ketone has a δ 190–180 ppm and carbonyl carbons of α-pyrone δ 165–155 pmm on average [ 27 , 28 , 29 ], the compounds were characterized by 1 H and 13 C NMR ( Supplementary Materials; Figures S1–S15 ).…”

Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

“…Chalcones are not only important intermediates in the biosynthesis of flavonoids, but are also valuable starting materials for the synthesis of biologically important heterocycles such as pyrazolines, isoxazolines, benzodiazepines and benzothiazepines (Zhuang et al, 2017;Ovonramwen et al, 2019). Chalcones and their derivatives have been reported to possess a number of interesting biological properties such as anti-inflammatory (Nurkenov et al, 2019;Vá squez-Martínez et al, 2019;Hsieh et al, 2000), anticancer (Dimmock et al, 1998;Bonakdar et al, 2017;Lim et al, 2020;Shaik et al, 2020), antioxidant (Ohkatsu & Satoh et al, 2008;Venkatachalam et al, 2012;Vá squez-Martínez et al, 2019;Shaik et al, 2020), antimicrobial (Fang et al, 2014;Vá squez-Martínez et al, 2019;Shaik et al, 2020) and anti-diabetic activities (Hsieh et al, 2012;Rammohan et al, 2020;Konidala et al, 2020). Besides that, compounds with a phenoxy-N-arylacetamide scaffold have demonstrated a variety of biological activities such as antimicrobial (Berest et al, 2011;Patel et al, 2013;Williams et al, 2015), antiviral (Paramonova et al, 2017), anti-diabetic (Li et al, 2015), anti-inflammatory (Rani et al, 2014), analgesic (Rani et al, 2014) and anticancer (Berest et al, 2011;Rani et al, 2014) activities.…”

Research progress of coumarins and their derivatives in the treatment of diabetes

“…Compared with diabetic rats treated with metformin (100 mg/kg b.d), further treatment with 80 and 81 at 30 mg/kg b.d. showed that MDA in pancreas and liver tissue of diabetic rats decreased significantly and moderately, while SOD and GSH rates increased 89 ( Figure 21 ).…”

“…Type II diabetes mellitus is one type of DM found in more than 90% of cases of DM and could be attributed to obesity, overweight and lack of physical activity, marked by pancreatic insulin release, when the body has not been trained to utilise insulin developed for glucose transfer, and the emergence of insulin resistance contributes to an increase of blood glucose or hyperglycaemia. 88 Therefore, the insulin receptor is a potential target for screening the anti-diabetic ligand activity of insulin receptor activator, and it is a tyrosine kinase transmembrane receptor, which effectively participates in the regulation of glucose homeostasis through phosphorylation of insulin binding 89–92 . A total of 54 coumarin chalcone hybrids were synthesised by the famous Biginelli synthesis, Pechmann condensation, acetylation and Claisen-Schmidt reaction.…”