Synthesis and biological activity of D3-trishomocubyl-4-amines.
The D3-trishomocubyl system was prepared from tertiary pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ols 5 in one step by using a modified Ritter reaction yielding only one of the possible two geometrical isomers of 4-amino-3-alkyl (or aryl)-D3-trishomocubane (8). Promising antagonism of reserpine-induced catalepsy was exhibited by these compounds which compared favorable with that of amantadine. Weak to mild anticholinergic properties were observed during the reduction of oxotremorine induced tremor and salivation procedure. Acute toxicities similar to that of amantadine were observed for some of these compounds. D3-Trishomocubyl-4-amines appeared as a promising new class of anti-Parkinson agents.
Oliver
D W
DW
Department of Pharmaceutical Chemistry, Pretoria College of Pharmacy, University of Pretoria, Republic of South Africa.
Dekker
T G
TG
Snyckers
F O
FO
Fourie
T G
TG
D000818:Animals; D000978:Antiparkinson Agents / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D002375:Catalepsy / Q000188:drug therapy; D055598:Chemical Phenomena; D002621:Chemistry; D008297:Male; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000978:Antiparkinson Agents; D001952:Bridged-Ring Compounds