476310-30-2Relevant academic research and scientific papers
Design and Development of a Common Synthetic Strategy for a Variety of 1-N-Iminosugars
Pandey, Ganesh,Kapur, Manmohan
, p. 3883 - 3886 (2002)
(Matrix Presented) A new synthetic strategy has been developed for a general approach toward the synthesis of a variety of 1-N-iminosugar-type glycosidase inhibitors utilizing precursors developed by the PET-mediated cyclization of α-trimethylsilylmethyla
Synthesis of polyhydroxy piperidines and their analogues: A novel approach towards selective inhibitors of α-glucosidase
Pandey, Ganesh,Bharadwaj, Kishor Chandra,Khan, M. Islam,Shashidhara,Puranik, Vedavati G.
supporting information; experimental part, p. 2587 - 2595 (2009/02/02)
Various polyhydroxy piperidine azasugars have been synthesized from precursors 18a and 18b, obtained in both enantiomeric forms from d-ribose. Out of these polyhydroxy piperidine azasugars, 22, 39 and 20 were found to be potent as well as selective inhibitors of α-glucosidase with Ki values ranging as low as 1.07 μM, 16.4 μM, and 88.2 μM, respectively. Replacement of the hydroxy methylene moiety of 19 (Ki 33% at 1 mM) by an amino methylene moiety (32, Ki 36.8 μM) showed a remarkable increase in the activity (almost 30 times). Furthermore, increasing the lipophilicity of 33 by N-alkylation with a dodecyl group (36) showed a three-fold enhancement in the activity (Ki 217 μM to Ki 72.3 μM). The Royal Society of Chemistry 2008.
A new access to polyhydroxy piperidines of the azasugar class: Synthesis and glycosidase inhibition studies
Pandey, Ganesh,Kapur, Manmohan,Islam Khan,Gaikwad, Sushama M.
, p. 3321 - 3326 (2007/10/03)
A new synthetic strategy has been devised to access a variety of polyhydroxylated piperidines belonging to the azasugar class of glycosidase inhibitors. The key precursor (3aR, 7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro[1,3]dioxo[4,5-c]pyridine is obtained by photoinduced electron transfer (PET) cyclization of the corresponding α-trimethylsilylmethylamine radical cation to the tethered acetylene functionality. The new molecules have been evaluated for inhibitory properties for certain β-glycosidases and have been found to be moderate to weak inhibitors of the enzymes under study.
