Synthesis of (S)-3,4-diaminobutanenitriles as precursors for 3-amino-GABA derivatives.
Starting from natural asparagine (1) a synthesis of the protected (S)-3,4-diaminobutanenitriles 5 and 8a-c via the beta-homoserine derivative 2 is described. The amino function in position 4 was introduced by Mitsunobu-coupling or by reductive amination when a strange deformylation of the amino aldehyde 7 was observed as a side reaction. The Mitsunobu-product 5 was converted into the dibenzylamine substituted GABA 6b which was investigated for its affinity at the GABA-A receptor.
Gmeiner
P
P
Pharmazeutisches Institut der Universität Bonn, Germany.
Hummel
E
E
Haubmann
C
C
Höfner
G
G
D000818:Animals; D001921:Brain / Q000378:metabolism; D002417:Cattle; D066298:In Vitro Techniques; D009570:Nitriles / Q000138:chemical synthesis* / Q000494:pharmacology; D018079:Receptors, GABA / Q000378:metabolism*; D005680:gamma-Aminobutyric Acid / Q000378:metabolism
D009570:Nitriles; D018079:Receptors, GABA; D005680:gamma-Aminobutyric Acid