537030-26-5Relevant academic research and scientific papers
Synthesis and inhibition study of bicyclic iminosugar-based alkaloids, scaffolds, and libraries towards glucosidase
Cheng, Wei-Chieh,Guo, Chih-Wei,Lin, Cheng-Kun,Jiang, Yu-Ruei
, p. 403 - 411 (2015/04/22)
A small library of bicyclic iminosugar-based alkaloids and scaffolds possessing a polyhydroxylated pyrrolidine and a varied ring skeleton have been synthesized. Through rapid diversification of the scaffold via an amide coupling with random carboxylic acids, structurally diverse bicyclic iminosugar-based libraries were prepared with substituent diversity, core diversity, and configurational diversity. This discovery process allowed us to efficiently sieve out potent and specific glycosidase inhibitors, and a bicyclic, conformationally restricted iminosugar was demonstrated to be more potent than the monocyclic ones in this study. The most potent and selective inhibitor discovered was found to have a Ki value of 71 nM against α-glucosidase.
6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures
D'Adamio, Giampiero,Parmeggiani, Camilla,Goti, Andrea,Moreno-Vargas, Antonio J.,Moreno-Clavijo, Elena,Robina, Inmaculada,Cardona, Francesca
, p. 6250 - 6266 (2014/08/05)
The synthesis of the first multivalent pyrrolizidine iminosugars is reported. The key azido intermediates 4 and 31 were prepared after suitable synthetic elaboration of the cycloadduct obtained from 1,3-dipolar cycloaddition of d-arabinose derived nitrone
Synthesis, biological evaluation and docking studies of casuarine analogues: Effects of structural modifications at ring B on inhibitory activity towards glucoamylase
Bonaccini, Claudia,Chioccioli, Matteo,Parmeggiani, Camilla,Cardona, Francesca,Lo Re, Daniele,Soldaini, Gianluca,Vogel, Pierre,Bello, Claudia,Goti, Andrea,Gratteri, Paola
experimental part, p. 5574 - 5585 (2011/02/19)
We report the total synthesis of a series of pyrrolizidine analogues of casuarine (1) and their 6-O-α-glucoside derivatives. The synthetic strategy is based on a totally regio- and stereoselective 1,3-dipolar cycloaddition of suitably substitutedalkenes a
Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone
Cardona, Francesca,Faggi, Enrico,Liguori, Francesca,Cacciarini, Martina,Goti, Andrea
, p. 2315 - 2318 (2007/10/03)
Practical syntheses of nitrone 8 by two different approaches from sugars are reported. Its use as a versatile intermediate in highly selective 1,3-dipolar cycloaddition reactions constitutes the key step for novel total syntheses of hyacinthacine A2
Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine
Carmona, Ana T.,Whigtman, Richard H.,Robina, Inmaculada,Vogel, Pierre
, p. 3066 - 3073 (2007/10/03)
Reaction of 1,4-anhydro-2,3,5-tri-O-benzyl-1-deoxy-1-imino-D-arabinitol N-oxide (8) with allyl alcohol produced a 3.6:1 mixture of the two pyrrolo[1,2-b]isoxazole derivatives 13 and 14. The major adduct 13 was converted to 7-deoxycasuarine (7), a potent,
