SYNTHESIS OF 1-BENZYL-3-[4-(ARYL-1-PIPERAZINYL) CARBONYL]-1H-INDOLES. NOVEL LIGANDS WITH POTENTIAL D4 DOPAMINERGIC ACTIVITY

被引：6

作者：

Pessoa-Mahana, Hernan ^{[1
]}

Cuevas, Ignacio M. ^{[1
]}

Pessoa-Mahana, David ^{[2
]}

Araya-Maturana, Ramiro ^{[1
]}

Fajardo, Iriux Almodovar ^{[1
]}

Barria, Claudio Saitz ^{[1
]}

机构：

[1] Univ Chile, Fac Chem & Pharmaceut Sci, Dept Organ & Phys Chem, Santiago 1, Chile

[2] Pontificia Univ Catolica Chile, Fac Chem, Dept Pharm, Santiago 22, Chile

来源：

JOURNAL OF THE CHILEAN CHEMICAL SOCIETY | 2011年 / 56卷 / 04期

关键词：

Indole; Arylpiperazines; dopaminergic activity; RECEPTOR ANTAGONISTS; 5-HT1A AGONISTS; BINDING; DERIVATIVES; INDOLE-2-CARBOXAMIDES; INHIBITORS; AFFINITY; INDOLES;

D O I：

10.4067/S0717-97072011000400009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of a series of functionalized 1-Benzyl-3[4-Aryl-1-piperazinyl]carbonyl-1H-Indoles 6(a-f), as a potential new class of bioactive ligands at D, receptors is reported. The synthetic strategy took place through a five steps sequence to provide indole amides 6(a-f) in 75-92% yield.

引用

页码：866 / 869

页数：4

共 15 条

[1] Indole-2-carboxamides as novel NR2B selective NMDA receptor antagonists [J].

Borza, I ;

Kolok, S ;

Gere, A ;

Agai-Csongor, É ;

Agai, B ;

Tárkányi, G ;

Horváth, C ;

Barta-Szalai, G ;

Bozó, É ;

Kiss, C ;

Bielik, A ;

Nagy, J ;

Farkas, S ;

Domány, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (21) :3859-3861

[2] Selective NR1/2B N-Methyl-d-aspartate receptor antagonists among indole-2-carboxamides and benzimidazole-2-carboxamides [J].

Borza, Istvan ;

Bozo, Eva ;

Barta-Szalai, Gizella ;

Kiss, Csilla ;

Tarkanyi, Gabor ;

Demeter, Adam ;

Gati, Tamas ;

Hada, Viktor ;

Kolok, Sandor ;

Gere, Aniko ;

Fodor, Laszlo ;

Nagy, Jozsef ;

Galgoczy, Kornel ;

Magdo, Ildiko ;

Agai, Bela ;

Fetter, Jozsef ;

Bertha, Ferenc ;

Keseru, Gyorgy M. ;

Horvath, Csilla ;

Farkas, Sandor ;

Greiner, Istvan ;

Domany, Gyorgy .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (05) :901-914

[3] Recent developments in indole ring synthesis-methodology and applications [J].

Gribble, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075

[4] Indolebutylamines as selective 5-HT1A agonists [J].

Heinrich, T ;

Böttcher, H ;

Bartoszyk, GD ;

Greiner, HE ;

Seyfried, CA ;

van Amsterdam, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (19) :4677-4683

[5] Dual 5-HT1A agonists and 5-HT re-uptake inhibitors by combination of indole-butyl-amine and chromenonyl-piperazine structural elements in a single molecular entity [J].

Heinrich, T ;

Böttcher, H ;

Schiemann, K ;

Hölzemann, G ;

Schwarz, M ;

Bartoszyk, GD ;

van Amsterdam, C ;

Greiner, HE ;

Seyfried, CA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4843-4852

[6] Cyanoindole derivatives as highly selective dopamine D4 receptor partial agonists:: Solid-phase synthesis, binding assays, and functional experiments [J].

Hübner, H ;

Kraxner, J ;

Gmeiner, P .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (23) :4563-4569

[7] Practical methodologies for the synthesis of indoles [J].

Humphrey, Guy R. ;

Kuethe, Jeffrey T. .

CHEMICAL REVIEWS, 2006, 106 (07) :2875-2911

[8] Azaindole derivatives with high affinity for the dopamine D4 receptor:: Synthesis, ligand binding studies and comparison of molecular electrostatic potential maps [J].

Löber, S ;

Hübner, H ;

Gmeiner, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (01) :97-102

[9] Phenylpiperazinylmethylindolecarboxylates and derivatives as selective D4-ligands [J].

Moll, A ;

Hübner, H ;

Gmeiner, P ;

Troschütz, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) :1671-1679

[10] Design, synthesis, and biological evaluation of dual binding site acetylcholinesterase inhibitors:: New disease-modifying agents for Alzheimer's disease [J].

Muñoz-Ruiz, P ;

Rubio, L ;

García-Palomero, E ;

Dorronsoro, I ;

del Monte-Millán, M ;

Valenzuela, R ;

Usán, P ;

de Austria, C ;

Bartolini, M ;

Andrisano, V ;

Bidon-Chanal, A ;

Orozco, M ;

Luque, FJ ;

Medina, M ;

Martínez, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (23) :7223-7233

← 1 2 →