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

页码：1388 / 1407

页数：20

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