2,3-Dihydro and carbocyclic analogs of tryptamines: interaction with serotonin receptors

Abstract

Several dihydro and carbocyclic analogues of tryptamine were evaluated in order to determine the role of the heterocyclic portion of the indole nucleus on the interaction of indolealkylamines with the serotonin receptors of the rat fundus. Reduction of the C2--C3 double bond or replacement of the indole nitrogen with an sp3-hybridized carbon atom results in a 50% decrease in receptor affinity. Complete removal of the five-membered ring of N,N-dimethyltryptamine reduces affinity by an order of magnitude. It appears that an intact indole nucleus, though not entirely necessary, results in an optimal receptor interaction for the indolealkylamines examined.

Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone

“…For the synthesis of the 5-amino derivative (Fig. 3, X ¼ CO; R 1 ¼ NH 2 ; R 2 ¼ H), the synthetic pathway began from the 3-acetamido-1,2,3,4-tetrahydroquinoline (4) obtained from 3-aminoquinoline by described procedures [27,28]. Reaction of 3 with triphosgene in the presence of Et 3 N in THF at 0 C followed by addition of methoxyamine hydrochloride afforded the methoxyurea 5 [22] in 66% yield (Scheme 1).…”

Duloxetine (Cymbalta™), a dual inhibitor of serotonin and norepinephrine reuptake

“…5 The aminopropanol was then arylated with 1-fluoronaphthalene, the resultant amino ether was then mono-demethylated in a two step process. Treatment with trichloroethylchloroformate and conversion of the resultant carbamate with zinc metal 0960-894X/$ -see front matter #…”

“…5 The aminopropanol was then arylated with 1-fluoronaphthalene, the resultant amino ether was then mono-demethylated in a two step process. …”

QSAR studies on hallucinogens

“…No other parameters, not even the most expected ones-FH0M0 and FLumo (energy of the lowest unoccupied MO)-were found to be correlated with pA2. However, eq [27][28][29][30][31][32][33][34] have also not been conclusive, as the number of data points used have been very small.…”