25390-67-4Relevant articles and documents
Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin
Bartolucci, Silvia,Mari, Michele,Di Gregorio, Giovanni,Piersanti, Giovanni
, p. 2233 - 2238 (2016/04/19)
Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.
N-arylsulfonylindole derivatives as serotonin 5-HT6 receptor ligands
Russell,Baker,Barden,Beer,Bristow,Broughton,Knowles,McAllister,Patel,Castro
, p. 3881 - 3895 (2007/10/03)
A series of N1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yl in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.
5-HT(1D) receptor agonist properties of novel 2-[5- [[(trifluoromethyl)sulfonyl]oxy]indolyl]ethylamines and their use as synthetic intermediates
Barf,De Boer,Wikstrom,Peroutka,Svensson,Ennis,Ghazal,McGuire,Smith
, p. 4717 - 4726 (2007/10/03)
2-[5-[[(Trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]ethylamine (18), its N,N'-di-n-propyl (12), N,N-diethyl (13), and N,N-dimethyl (14) derivatives, and 4-[3-[2-(N,N-dimethylamino)ethyl]-1H-indol-3-yl]-N-(p- methoxybenzyl)acrylamide (GR46611, 19) were syn
