'On water' synthesis of dibenzo-[1,4]-diazepin-1-ones using l-proline as an organocatalyst and under catalyst-free conditions, and their evaluation as α-glucosidase inhibitors

Autor:	Dhurke Kashinath, P Onkara Perumal, Sakkani Nagaraju, K. Divakar, Banoth Paplal
Rok vydání:	2017
Předmět:	010405 organic chemistry Chemistry Stereochemistry General Chemistry 010402 general chemistry 01 natural sciences Catalysis In vitro 0104 chemical sciences Residue (chemistry) Materials Chemistry medicine Proline Homology modeling Binding site IC50 Acarbose medicine.drug
Zdroj:	New Journal of Chemistry. 41:8993-9001
ISSN:	1369-9261 1144-0546
Popis:	Functionalized dibenzo-[1,4]-diazepin-1-ones were synthesized using the “on-water” concept in the presence of L-proline (organocatalyst; 20 mol%) and under catalyst free conditions (sealed tube) in an aqueous medium. The resulting molecules were tested (in vitro) for α-glucosidase (isolated from Saccharomyces cerevisiae) enzyme inhibition using acarbose as a standard drug (IC50 32.47 ± 1.64). The enzyme inhibition kinetic analysis of selected molecules showed the competitive mode of inhibition (best result; IC50 39.31 ± 1.68) against α-glucosidase. Molecular docking studies of these compounds with the MAL12 homology model showed HIS279A as a major interacting residue in the binding site of the protein which is a similar binding mode consistent with the binding of acarbose.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a108ddf231958d7a4128bda660504b44 https://doi.org/10.1039/c7nj01021d Zobrazit plný text záznamu