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Synthesis and Biological Screening of Novel Indolalkyl Arenes Targeting the Serotonine Transporter
Author(s) -
OjedaGómez Claudia,
PessoaMahana Hernán,
IturriagaVásquez Patricio,
PessoaMahana Carlos David,
RecabarrenGajardo Gonzalo,
MéndezRojas Claudio
Publication year - 2014
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201300321
Subject(s) - chemistry , affinities , binding affinities , stereochemistry , transporter , serotonin transporter , in vitro , nucleophile , chemical synthesis , nucleophilic substitution , sequence (biology) , biological activity , combinatorial chemistry , serotonin , organic chemistry , biochemistry , receptor , gene , catalysis
A series of functionalized indolylalkylarenes 3 – 16 ( a and b ) were synthesized and their affinities for the serotonin transporter were investigated in vitro . Compounds 3 – 12 ( a and b ) were obtained by nucleophilic substitution of 3‐(1 H ‐indol‐3‐yl)propyl‐4‐methylbenzenesulfonates 2 ( a and b ) with a series of azaheterocycles. Compounds 14 – 16 ( a and b ) were prepared in a two‐step sequence by reaction of 3‐(1 H ‐indol‐3‐yl)‐2‐methylpropanal with substituted 1,2‐phenylenediamines. Compounds 3b , 4b , and 5b showed good binding affinities ( K i = 33.0, 48.0, and 17 nM, respectively). The other synthesized compounds showed moderate or no affinity in the binding studies.