Synthesis of vinca alkaloids and related compounds. Part 84. Sulfonamide derivatives of some vinca alkaloids with cardiovascular activity.
(+)-Vincamine (1) and (+)-vinpocetine (2) were chlorosulfonylated and the resulting sulfonyl chloride isomers (3-6) were transformed into sulfonamides (7-10). The ester group of sulfonamides was modified by selective hydrolysis and transesterification. Apovincaminol derivatives (14-16) were also prepared by reduction. In addition to the known cerebrovascular effects of the unsubstituted compounds (1,2) sulfonamides also show a significant peripheral vasodilator effect.
Moldvai
I
I
Central Research Institute for Chemistry, Hungarian Academy of Sciences, Budapest, Hungary.
Temesvári-Major
E
E
Szántay
C
C
Tóth
G
G
Kárpáti
E
E
Szántay
C
C
D000818:Animals; D001783:Blood Flow Velocity / Q000187:drug effects; D001794:Blood Pressure / Q000187:drug effects; D004285:Dogs; D005260:Female; D006439:Hemodynamics / Q000187:drug effects* / Q000502:physiology; D000860:Hypoxia; D008297:Male; D015394:Molecular Structure; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014664:Vasodilation / Q000187:drug effects*; D014748:Vinca Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014749:Vincamine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D013449:Sulfonamides; D014748:Vinca Alkaloids; C063621:apovincamine; D014749:Vincamine