653571-07-4Relevant academic research and scientific papers
Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives
Concia, Alda Lisa,Gómez, Livia,Bujons, Jordi,Parella, Teodor,Vilaplana, Cristina,Cardona, Pere Joan,Joglar, Jesús,Clapés, Pere
, p. 2005 - 2021 (2013/06/04)
A chemo-enzymatic strategy for the preparation of 2-aminomethyl derivatives of (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol (also called 1,4-dideoxy-1,4-imino-d-arabinitol, DAB) and its enantiomer LAB is presented. The synthesis is based on the enzymatic preparation of DAB and LAB followed by the chemical modification of their hydroxymethyl functionality to afford diverse 2-aminomethyl derivatives. This strategy leads to novel aromatic, aminoalcohol and 2-oxopiperazine DAB and LAB derivatives. The compounds were preliminarily explored as inhibitors of a panel of commercial glycosidases, rat intestinal disaccharidases and against Mycobacterium tuberculosis, the causative agent of tuberculosis. It was found that the inhibitory profile of the new products differed considerably from the parent DAB and LAB. Furthermore, some of them were active inhibiting the growth of M. tuberculosis.
Synthesis and glycosidase inhibitory activities of 2-(aminoalkyl) pyrrolidine-3,4-diol derivatives
Carmona, Ana T.,Popowycz, Florence,Gerber-Lemaire, Sandrine,Rodriguez-Garcia, Eliazar,Schuetz, Catherine,Vogel, Pierre,Robina, Inmaculada
, p. 4897 - 4911 (2007/10/03)
Several 2-(aminomethyl)-and 2-(2-aminoethyl)-pyrrolidine-3,4-diol derivatives have been assayed for their inhibitory activities towards glycosidases. Good inhibitors of α-mannosidases must have the (2R,3R,4S) configuration and possess 2-(benzylamino)methy
Synthesis and α-mannosidase inhibitory evaluation of (2R,3R,4S)- and (2S,3R,4S)-2-(aminomethyl)pyrrolidine-3,4-diol derivatives
Popowycz, Florence,Gerber-Lemaire, Sandrine,Rodriguez-Garcia, Eliazar,Schuetz, Catherine,Vogel, Pierre
, p. 1914 - 1948 (2007/10/03)
The synthesis of 46 derivatives of (2R,3R,4S)-2-(aminomethyl)pyrrolidine-3,4-diol is reported (Scheme 1 and Fig. 3), and their inhibitory activities toward α-mannosidases from jack bean (B) and almonds (A) are evaluated (Table). The most-potent inhibitors
Derivatives of (2R,3R,4S)-2-aminomethylpyrrolidine-3,4-diol are selective α-mannosidase inhibitors
Popowycz, Florence,Gerber-Lemaire, Sandrine,Demange, Raynald,Rodriguez-Garcia, Eliazar,Asenjo, Ana Teresa Carmona,Robina, Inmaculada,Vogel, Pierre
, p. 2489 - 2493 (2007/10/03)
A collection of (2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl derivatives have been tested for their inhibitory activities toward 25 glycosidases. Competitive (Ki = 7.4 μM) and selective inhibition of α-mannosidase from jack bean has been found for (
