Novel Coumarin Containing Dithiocarbamate Derivatives as Potent α-Glucosidase Inhibitors for Management of Type 2 Diabetes was written by Mollazadeh, Marjan;Mohammadi-Khanaposhtani, Maryam;Valizadeh, Yousef;Zonouzi, Afsaneh;Faramarzi, Mohammad A.;Kiani, Mitra;Biglar, Mahmood;Larijani, Bagher;Hamedifar, Haleh;Mahdavi, Mohammad;Hajimiri, Mir Hamed. And the article was included in Medicinal Chemistry (Sharjah, United Arab Emirates) in 2021.Product Details of 109-85-3 The following contents are mentioned in the article:
α-Glucosidase is a hydrolyzing enzyme that plays a crucial role in the degradation of carbohydrates and starch to glucose. Hence, α-glucosidase is an important target in carbohydrate mediated diseases such as diabetes mellitus. In this study, novel coumarin containing dithiocarbamate derivatives 4a-n were synthesized and evaluated against α-glucosidase in vitro and in silico. These compounds were obtained from the reaction between 4-(bromomethyl)-7-methoxy-2H-chromen-2-one 1, carbon disulfide 2, and primary or secondary amines 3a-n in the presence of potassium hydroxide and ethanol at room temperature In vitro α-glucosidase inhibition and kinetic study of these compounds were performed. Furthermore, a docking study of the most potent compounds was also performed by Auto Dock Tools (version 1.5.6). Obtained results showed that all the synthesized compounds exhibited prominent inhibitory activities (IC50 = 85.0 ± 4.0-566.6 ± 8.6 μM) in comparison to acarbose as a standard inhibitor (IC50 = 750.0 ± 9.0 μM). Among them, the secondary amine derivative 4d with pendant indole group was the most potent inhibitor. Enzyme kinetic study of the compound 4d revealed that this compound competes with a substrate to connect to the active site of α-glucosidase and therefore is a competitive inhibitor. Moreover, a mol. docking study predicted that this compound interacted with the α-glucosidase active site pocket. Our results suggest that the coumarin-dithiocarbamate scaffold can be a promising lead structure for designing potent α-glucosidase inhibitors for the treatment of type 2 diabetes. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Product Details of 109-85-3).
2-Methoxyethylamine (cas: 109-85-3) belongs to ethers. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Product Details of 109-85-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem