1240486-41-2Relevant academic research and scientific papers
A highly expeditious synthesis of a bicyclic iminosugar using the novel key step of [NMM]+[HSO4]- promoted conjugate addition and Mitsunobu reaction
Prasad, Virendra,Kumar, Dhananjay,Tiwari, Vinod K.
, p. 5794 - 5797 (2013)
A simple and highly facile protocol has been developed for the stereoselective synthesis of 1-deoxy-norcastanospermine from readily available d-glucose. N-Methylmorpholinium hydrogen sulphate was seen for the first time as a suitable catalyst for the faci
Synthesis, computational study and glycosidase inhibitory activity of polyhydroxylated conidine alkaloids - A bicyclic iminosugar
Sanap, Shrihari P.,Ghosh, Sougata,Jabgunde, Amit M.,Pinjari, Rahul V.,Gejji, Shridhar P.,Singh, Shailza,Chopade, Balu A.,Dhavale, Dilip D.
experimental part, p. 3307 - 3315 (2010/08/21)
New bicyclic conidine iminosugars 1d and 1e were synthesized from d-glucose. Thus, d-glucose was converted to sugar β-amino acids 3a and 3b in good yields. Individual treatment of 3a/3b with the Mukaiyama reagent afforded sugar β-lactams 4a/4b that on reduction with LiAlH 4/AlCl3 gave azetidines 5a/5b with a sugar appendage. Reductive aminocyclization of sugar azetidines 5a/5b afforded the corresponding conidine iminosugars 1d/1e. Based on the 1H NMR and DFT calculation studies the conformation of 1d was assigned as half chair A2 and that of 1e as a boat B2. The glycosidase inhibitory activities of 1d and 1e such as α-mannosidase, α-glucosidase and α-galactosidase were studied. The α-amylase activity was compared with acarbose. Compound 1d was found to be a moderate inhibitor of glycosidases while 1e was noticed to be a good inhibitor of α-mannosidase and a moderate inhibitor of other glycosidases. These results were substantiated by molecular docking studies using WHAT IF software and the AUTODOCK 3.0 program. The Royal Society of Chemistry 2010.
