[Lactones. 28. EPC-synthesis, structure and pharmacology of "lactonized" and "lactamized" analogues of acetylcholine].
The enantiopure gamma-aminomethyl-gamma-butyrolactones (S)- and (R)-4a-d represent constrained analogues of acetylcholine, which were synthesized from D- or L-glutamic acid following two different routes. In addition, the corresponding lactames (S)- and (R)-10 were prepared by enantioselective synthesis. Only moderate activity was found at acetylcholine sites at the guinea pig atrium.
Pieper
B
B
Pharmazeutisches Institut, Universität Bonn.
Tränkle
C
C
Nieger
M
M
Mohr
K
K
Lehmann
J
J
D000109:Acetylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D003460:Crystallization; D018698:Glutamic Acid / Q000737:chemistry; D006168:Guinea Pigs; D006321:Heart / Q000187:drug effects; D066298:In Vitro Techniques; D008968:Molecular Conformation; D011976:Receptors, Muscarinic / Q000187:drug effects / Q000378:metabolism; D013237:Stereoisomerism
D011976:Receptors, Muscarinic; D018698:Glutamic Acid; D000109:Acetylcholine
EPC-Synthese, Struktur und Pharmakologie "lactonisierter" und "lactamisierter" Acetylcholin-Analoga. Lactone, 28. Mitteilung.