Two new bioactive indole alkaloids, 5-hydroxytryptamine (serotonin) N-4-oxobutanoic acid and 5-hydroxytryptamine N-acetyl-N-pyrrolecarboxarnide , named as bufobutanoic acid (2) and bufopyramide (3), respectively, were isolated from the Chinese traditional drug Ch'an Su in addition to known bufotenine (1).The structures were elucidated on the basis of spectroscopic data.Bufobutanoic acid (2) and...
Heterocycles1999Haruhisa Shirahama, Kazuyo Sogawa, Kimiko Hashimoto1 citation
H-D exchange experiment?were performed on psilocin (1) and its analogs in MeOH-d,.The various exchange rates depending on their C3- suhstituents were observed.The exchange of bufotenine (5) and 5hydroxyindole ( 7) is much slower than psilocin (1) and its analogs (2 -4).Psilocin ( 1) is a hallucinogenic principle isolated from the poisonous mushroom, Psilocybe rnericanq' and it was recently...
Simple syntheses of serotonin (la), N-methylserotonin (lb), bufotenine (lc), and melatonin (2), and the first total synthesis of N-(indol-3-y1)methyl-N-methyl-5-methoxytryptamine (3) from tryptamine (4a) are reported through acid catalyzed nucleophilic substitution reaction of 1-hydroxytryptamines.Tryptamine alkaloids such as serotonin (la, Scheme l)? N-methylserotonin (lb)?bufotenine (lc) ?arb
Various types of 1-hydroxyindoles were prepared for the first time.Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1 -hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.~espedaminez (1 a, Scheme 1) was isolated from Lespedeza bicolorvar.japonica Nakai and -b r o m o -~, ~-d i m e t h ~l t r y ~t a m i...
A general synthetic method of 4-substituted indoles was examined.The Fischer indolization of phenylhydrazones (2, 3, 7, and 8) having chlorine on & position gave 7-chloro-4-substituted indoles (4, 9, and lo), which were converted to 4-substituted indoles (5 and 13) by catalytic hydrogenation.Cyclization of 3-(2-ethoxy~arbonyl-7-chloroindol-4-yl)propionic acid (10) with polyphosphoric acid (PPA)...