Synthesis and analgesic activity of N,N'-dicarbonyltryptamines.
5-Methoxytryptamine and L-tryptophan methyl ester were acylated with malonic acid, dimethyl malonate, or succinic anhydride to produce the corresponding N,N'-dicarbonyltryptamine derivatives. The analgesic activity was evaluated by the tail flick test. All of the compounds exhibited desirable analgesic potency. This result is consistent with that of N-(N-acetyl-L-tryptophanyl)-5-methoxytryptamine and confirmed that introducing substituted tryptamine into the amide chain of melatonin does enhance analgesic potency.
College of Pharmaceutical Sciences, Beijing Medical University, P. R. China.
H
H
Dongmei
W
W
Chao
Z
Z
Ming
P
P
Shiqi
D008735:5-Methoxytryptamine / Q000031:analogs & derivatives* / Q000494:pharmacology; D000215:Acylation; D000700:Analgesics / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D008297:Male; D008314:Malonates / Q000737:chemistry; D051379:Mice; D008813:Mice, Inbred ICR; D008968:Molecular Conformation; D010147:Pain Measurement; D013329:Structure-Activity Relationship; D013387:Succinic Anhydrides / Q000737:chemistry; D014363:Tryptamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000700:Analgesics; D008314:Malonates; D013387:Succinic Anhydrides; D014363:Tryptamines; D008735:5-Methoxytryptamine; C028129:tryptophan methyl ester; D014364:Tryptophan; C030290:malonic acid; C005230:methyl malonate