A new series of biscoumarin derivatives 3a-n were synthesized and evaluated for their α-glucosidase inhibitory activities. The reaction of the 4aminocoumarin with benzaldehyde derivatives led to the formation of the title compounds in good yields. All the synthesized compounds showed potent αglucosidase inhibitory activity with IC50 ranging from 20.0 ± 0.7 to180.1 ± 0.8 µM, in comparison with acarbose as the standard drug (IC50 = 750.0 1.5 µM). Among the synthesized compounds, 3,3'-(p-tolylmethylene)bis(4-amino-2Hchromen-2-one) 3c was found to be the most active compound with an IC50 value of 20.0 ± 0.7 µM. Kinetic study exhibited that compound 3c was a competitive inhibitor against α-glucosidase (Ki = 22.4 µM). In silico docking study for the most potent compound 3c was also performed.
Background and the purpose of the studyModified androsterone derivatives are class of steroidal compounds with potential anticancer properties. Various steroidal derivatives containing substitution at position 16 have shown diversified pharmacological activities. In the present study, a new series of cytotoxic 16-(substituted benzylidene) derivatives of dehydroepiandrosterone (DHEA) were synthesized and evaluated against three different cancer cell lines.MethodsThe cytotoxic 16-(substituted benzylidene) derivatives of DHEA were synthesized via aldol condensation of DHEA with corresponding benzaldehyde derivatives. The cytotoxic activity of synthesized derivatives was evaluated against three different cancer cells including KB, T47D and SK-N-MC cell lines by MTT reduction colorimetric assay.ResultsThe results indicated that 16-(substituted benzylidene) derivatives of DHEA could be served as a potent anti-cancer agent. The 3-cholro benzylidene derivatives of DHEA was the most potent synthesized derivative especially against KB and T47D cell lines (IC50 values were 0.6 and 1.7 μM; respectively).ConclusionThe cytotoxic potential of novel benzylidene derivatives of DHEA is mainly attributed to the position and nature of the substituted group on the benzylidene pendant.
Huisgen cycloaddition reaction has been originally utilized for the synthesis of 1, 2, 3-triazoles regioisomers. In this review, its stereochemistry and also mechanistical features of Huisgen cycloaddition reaction based on the quantum chemistry are highlighted.Thermal and copper catalyzed approaches to the synthesis of 1,2,3-triazoles will also be re-visited. Finally, the synthesis of alternative region-isomer, 1,5-disubstituted-1,2,3-triazoles under ruthenium catalysis and transition metal free conditions is described.
The simple and facile strategy for the synthesis of 2,3-disubstitutedchromeno[4,3-b]pyrrole-4(1H)-ones has been established. This method describes the Kornblum oxidation reaction of acetophenones, followed by the Knoevenagle treatment of the resulted (het)arylglyoxals with active methylene compounds and consequently iodine-activated Michael type reaction with 4amino coumarin in a one-pot manner to afford disubstituted chromeno[4,3b]pyrrole-4(1H)-one derivatives.
In this paper, a new series of isatin-sulphonamide based derivatives were designed, synthesised and evaluated as caspase inhibitors. The compounds containing 1-(pyrrolidinyl)sulphonyl and 2-(phenoxymethyl)pyrrolidin-1-yl)sulphonyl substitution at C5 position of isatin core exhibited better results compared to unsubstituted derivatives. According to the results of caspase inhibitory activity, compound 20d showed moderate inhibitory activity against caspase-3 and À7 in vitro compared to Ac-DEVD-CHO (IC 50 ¼ 0.016 ± 0.002 lM). Among the studied compounds, some active inhibitors with IC 50s in the range of 2.33-116.91 lM were identified. The activity of compound 20d was rationalised by the molecular modelling studies exhibiting the additional van der Waals interaction of N-phenylacetamide substitution along with efficacious T-shaped p-p and pi-cation interactions. The introduction of compound 20d with good caspase inhibitory activity will help researchers to find more potent agents.
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