406934-66-5Relevant articles and documents
[1,2,4]Triazole derivatives as 5-HT1A serotonin receptor ligands
Sarva, Maria Concetta,Romeo, Giuseppe,Guerrera, Francesco,Siracusa, Mariangela,Salerno, Loredana,Russo, Filippo,Cagnotto, Alfredo,Goegan, Mara,Mennini, Tiziana
, p. 313 - 323 (2007/10/03)
A series of new 4-amino-3-[3-[4-(2-methoxy or nitro phenyl)-1-piperazinyl] propyl]thio]-5-(substitutedphenyl)[1,2,4]triazoles 11a-t was synthesized in order to obtain compounds with high affinity and selectivity for 5-HT1A receptor over the α1-adrenoceptor. A series of isomeric 4-amino-2-[3-[4-(2-methoxy or nitro phenyl)-1-piperazinyl]propyl]-5-(substitutedphenyl)-2,4-dihydro-3H[1,2,4]triazole-3-thiones 12a-r was also isolated and characterized. New compounds were tested to evaluate their affinity for 5-HT1A receptor and α1-adrenoceptor in radioligand binding experiments. As a general trend, triazoles 11a-t showed a preferential affinity for the 5-HT1A receptor whereas isomeric 2,4-dihydro-3H[1,2,4]triazole3-3-thiones 12a-r preferentially bind to the α1-adrenoceptor site. Several molecules showed affinities in the nanomolar range and 4-amino-3-[3-[4-(2-methoxyphenyl)-1-piperazinyl]thio]-5-(4-propyloxy-phenyl)[1,2,4]triazole (11o) was the most selective derivative for the 5-HT1A receptor (Kiα1/Ki5-HT1A=55). The decrease in 5-HT1A=55). The decrease in 5-HT1A = 55). The decrease in 5-HT1A receptor selectivity in 3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]thio]-5-(substitutedphenyl) [1,2,4] triazole 14a-b, lacking in the amino group in 4-position of the triazole ring, in comparison with their analogues in the series 11a-t, suggest that the amino function represents a critical structural feature in derermining 5-HT1A receptor selectivity in this class of compounds. Copyright
