111193-64-7Relevant academic research and scientific papers
Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists
Chiba, Jun,Takayama, Gensuke,Takashi, Tohru,Yokoyama, Mika,Nakayama, Atsushi,Baldwin, John J.,McDonald, Edward,Moriarty, Kevin J.,Sarko, Christopher R.,Saionz, Kurt W.,Swanson, Robert,Hussain, Zahid,Wong, Angela,MacHinaga, Nobuo
, p. 2725 - 2746 (2007/10/03)
A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12 ml/min/kg and 11p, 9 ml/min/kg).
Straightforward Synthesis of Pyrrolidine Glycosidase Inhibitors via Asymmetric Hetero-Diels-Alder Reaction
Defoin, Albert,Sifferlen, Thierry,Streith, Jacques
, p. 1294 - 1296 (2007/10/03)
Base-catalysed rearrangement of the oxazine-carboxylate 8, obtained from pentadienoic acid 4 by asymmetric hetero-Diels-Alder reaction followed by simple chemical transformations, led to the protected trihydroxy-proline 9. Using various reduction conditions, the potent glycosidase inhibitors 1,4-dideoxy-1,4-imino-D-lyxitol D-1 and 1,4-dideoxy-1,4-imino-L-ribitol L-2 were obtained.
Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives
Goli, Deepa M.,Cheesman, Bruce V.,Hassan, Mohamed E.,Lodaya, Rita,Slama, James T.
, p. 219 - 242 (2007/10/02)
(2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters.The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave hi
