Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors

被引：13
|
作者：
Pessoa-Mahana, Hernan [1 ]
Recabarren-Gajardo, Gonzalo [2 ]
Fiedler Temer, Jenny [3 ]
Zapata-Torres, Gerald [4 ]
David Pessoa-Mahana, C. [2 ]
Saitz Barria, Claudio [1 ]
Araya-Maturana, Ramiro [1 ]
机构：
[1] Univ Chile, Dept Quim Organ & Fisicoquim, Fac Ciencias Quim & Farmaceut, Santiago 1, Chile
[2] Pontificia Univ Catolica Chile, Fac Quim, Dept Farm, Santiago 22, Chile
[3] Univ Chile, Dept Bioquim & Biol Mol, Fac Ciencias Quim & Farmaceut, Santiago 1, Chile
[4] Univ Chile, Unidad Graf Mol, Dept Quim Inorgan & Analit, Fac Ciencias Quim & Farmaceut, Santiago 1, Chile
来源：
MOLECULES | 2012年 / 17卷 / 02期
关键词：
arylpiperazines; benzo[b]thiophene; depression; 5-HT1A receptor; docking; microwave Michael addition; DUAL-ACTION; POTENTIAL ANTIDEPRESSANTS; BINDING; TRANSPORTER; LIGANDS; PART; ARYLPIPERAZINES; AGONIST; ENERGY;
D O I：
10.3390/molecules17021388
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of novel benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one derivatives 6a-f, 7a-f and their corresponding alcohols 8a-f were synthesized and evaluated for their affinity towards 5-HT1A receptors. The influence of arylpiperazine moiety and benzo[b]thiophene ring substitutions on binding affinity was studied. The most promising analogue, 1-(benzo[b]thiophen-2-yl)-3-(4-(pyridin-2-yl)piperazin-1-yl)propan-1-one (7e) displayed micromolar affinity (K-i = 2.30 mu M) toward 5-HT1A sites. Docking studies shed light on the relevant electrostatic interactions which could explain the observed affinity for this compound.
引用
收藏
页码：1388 / 1407
页数：20
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