RT Journal Article
T1 Synthesis and dopaminergic activity of a series of new 1-aryl tetrahydroisoquinolines and 2-substituted 1-aryl-3-tetrahydrobenzazepines.
A1 Lucena-Serrano, Cristina
A1 Lucena-Serrano, Ana
A1 Rivera-Ramírez, Alicia
A1 López-Romero, Juan Manuel
A1 Valpuesta-Fernández, María
A1 Díaz-Morilla, Amelia
K1 Dopamina - Receptores
K1 Química biorgánica
AB A series of new 1-aryl-6,7-dihydroxy tetrahydroisoquinolines with several substitution patterns in the 1-aryl group at C-1 were prepared in good yields. The influence of each substituent on the affinity and selectivity for D1 and D2 dopaminergic receptors was studied. Moreover, N-alkyl salts of these tetrahydroisoquinolines were used as starting material to synthesize a series of new 1-aryl-7,8-dihydroxy 3-tetrahydrobenzazepines derivatives with electron-withdrawing substituents at C-2 position by the diastereoselective Stevens rearrangement. The structure-activity relationship of these compounds was explored to evaluate the effect of the functional group at C-2 in benzazepines and the modification in the aryl group at the isoquinoline C-1 position towards the affinity and selectivity for the mentioned receptors. The 1-aryl-6,7-dihydroxy tetrahydroisoquinoline 4c shows significant affinity towards D2 receptor, with Ki value of 31 nM. This significant affinity can be attributed to the presence of a thiomethyl group, and it is the most active 1-aryl-6,7-dihydroxy tetrahydroisoquinoline derivative reported to date.
PB Elsevier
YR 2018
FD 2018-07-05
LK https://hdl.handle.net/10630/29331
UL https://hdl.handle.net/10630/29331
LA eng
NO Lucena-Serrano, C., Lucena-Serrano, A., Rivera, A., López-Romero, J. M., Valpuesta, M., & Díaz, A. (2018). Synthesis and dopaminergic activity of a series of new 1-aryl tetrahydroisoquinolines and 2-substituted 1-aryl-3-tetrahydrobenzazepines. Bioorganic Chemistry, 80, 480–491
NO This research was supported by the Spanish “Ministerio de Economía, Industria y Competividad” Project CTQ 2016-76311-P.
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 21 ene 2026