Data for: The first target specific, highly diastereoselective synthesis, design and characterization of pyranoquinolinyl acrylic acid diasteromers as potential α-glucosidase inhibitors.

Published: 27 November 2018| Version 1 | DOI: 10.17632/t8624bnckt.1
Magesh C J, Sathishkumar R, Jayasudha R, Lavanya G, Venkatapathy K, Ramanathan M


In the present investigation we report the first target specific, highly diastereoselective synthesis of new class of pyranoquinolinyl/furoquinolinyl-acrylic acid diastereomers and evaluation of their in vitro α-glucosidase inhibitory activity. All the products were thoroughly characterized by 1H-NMR, 13C-NMR, FT-IR, Mass spectral and CHN analysis. A highly diastereoselective target specific route of synthesis for the biologically active diastereomers were developed by using chiral catalyst Europium tris[3-heptafluoropropylhydroxyl methylene]-(-)-camporate (A) or Europium tris[3-(trifluoromethyl)hydroxylmethylene]-(+)-camporate (B). It was found that among a set of 4 diastereomeric products obtained, exo diasteromers of pyranoquinolinyl acrylic acid adducts exhibited relatively high α-glucosidase inhibitory activity. The newly synthesized compounds exhibited IC50 values in the range of (0.40 ± 0.02 - 30.3 ± 0.84μM) as compared to standard acarbose (IC50=0.65± 0.02μM). It was found that compounds 11a, 11c, 11d and 12d were found to be more active than standard acarbose. It was also found that unsubstituted compound (11a) or compounds with chlorine or methoxy substituent (11c, 11d, 12d) showed potential α-glucosidase inhibitory activity. However a reversal in activity was observed with Nitro substituent (11b, 13b) wherein the endo diastereomers were found to be more active than exo diastereomers. Molecular docking studies were used for design of the compound and understand the mode of binding between the compound and target enzyme. A plausible mechanism for the diastereoselective synthesis was also proposed.