Synthesis of Benzo[b]thiophene Carboxamides Connected to 4‐Arylpiperazines through a Benzylic Spacer: Potential Ligands with 5‐HT_1A Binding Affinity

References

• Caliendo , G. , Santagada , V. , Perissutti , E. and Fiorino , F. 2005 . Derivatives as 5‐HT1A receptor ligands–Past and present . Curr. Med. Chem. , 12 ( 15 ) : 1721 – 1753 .
   PubMed Web of Science ®Google Scholar
• Pessoa‐Mahana , H. , Araya‐Maturana , R. , Saitz , B. C. and Pessoa‐Mahana , C. D. 2003 . A synthetic overview of antidepressants with 5‐HT1A binding affinities . Minirev. Med. Chem. , 3 ( 2 ) : 77 – 93 .
   Google Scholar
• López‐Rodríguez , M. L. , Ayala , D. , Benhamú , B. and Morcillo , M. J. 2002 . Arylpiperazine derivatives acting at 5‐HT1A Receptors . Curr. Med. Chem. , 9 ( 4 ) : 443 – 469 .
   PubMed Web of Science ®Google Scholar
• Martínez , J. , Pérez , S. , Oficialdegui , A. M. , Heras , B. , Orús , L. , Villanueva , H. , Palop , J. A. , Roca , J. , Mourelle , M. , Bosch , A. , Del Castillo , J. C. , Lasheras , B. , Tordera , R. , Del Río , J. and Monge , A. 2001 . New 3‐[4‐(aryl)piperazin‐1‐yl]‐1‐(benzo[b]thiophen‐3‐yl) propane derivatives with dual action at 5‐HT1A serotonin transporter as a new class of antidepressants . Eur.J. Med. Chem. , 36 : 55 – 61 .
   PubMedGoogle Scholar
• Pessoa‐Mahana , H. , Recabarren , G. G. , Araya‐Maturana , R. , Koshe Cárcamo , J. and Pessoa‐Mahana , C. D. 2004 . Synthesis of 4‐arylpiperazine derivative of moclobemide: Potential antidepressants with a dual mode of action . Synth. Commun. , 34 ( 14 ) : 2513 – 2521 .
   Web of Science ®Google Scholar
• Zajdel , P. , Subra , G. , Bojarski , A. J. , Duszynska , B. , Pawłowski , M. and Martinez , J. 2006 . Arylpiperazines with N‐acylated amino acids as 5‐HT1A receptor ligands . Bioorg. Med. Chem. Lett. , 16 : 3406 – 3410 .
   PubMedGoogle Scholar
• Kling , A. , Lange , U. E. W. , Mack , H. , Bakker , M. H. M. , Drescher , K. U. , Hornberger , W. , Hutchins , C. W. , Möller , A. , Müller , R. , Schmidt , M. , Unger , L. , Wicke , K. , Schellhaasc , K. and Steinerc , G. 2005 . Synthesis and SAR of highly potent dual 5‐HT1A and 5‐HT1B antagonists as potential antidepressant drugs . Bioorg. Med. Chem. Lett. , 15 : 5567 – 5573 .
   PubMed Web of Science ®Google Scholar
• Scott , C. , Soffin , E. M. , Hill , M. , Atkinson , P. J. , Langmead , C. J. , Wren , P. B. , Faedo , S. , Gordon , L. J. , Price , G. W. , Bromidge , S. , Johnson , C. N. , Hagan , J. J. and Watson , J. 2006 . SB‐649915, a novel, potent 5‐HT1A and 5‐HT1B autoreceptor antagonist and 5‐HT re‐uptake inhibitor in native tissue . Eur. J. Pharmacol. , 536 ( 1–2 ) : 54 – 61 .
   PubMedGoogle Scholar
• Kossakowski , J. , Krawiecka , M. and Kuran , B. 2006 . Synthesis of conformationally constrained aryl‐ or heteroaryl‐piperazinyl derivatives of selected imides as 5‐HT1A receptor ligands . Molecules , 11 ( 8 ) : 615 – 626 .
   PubMed Web of Science ®Google Scholar
• Zlatović , M. V. , Sukalović , V. V. , Schneider , C. and Roglić , G. M. 2006 . Interaction of arylpiperazine ligands with the hydrophobic part of the 5‐HT1A receptor binding site . Bioorg. Med. Chem. , 14 : 2994 – 3001 .
   PubMed Web of Science ®Google Scholar
• Bojarski , A. J. , Paluchowska , M. H. , Dusznyska , B. , Bugno , R. , Kłodzinska , A. , Tatarczynska , E. and Chojnacka‐Wojcik , E. 2006 . Structure–intrinsic activity relationship studies in the group of 1‐imido/amido substituted 4‐(4‐arylpiperazin‐1‐yl) cyclohexane derivatives: New, potent 5‐HT1A receptor agents with anxiolytic‐like activity . Bioorg. Med. Chem. , 14 : 1391 – 1402 .
   PubMedGoogle Scholar
• Takeuchi , K. , Kohn , T. J. , Honigschmidt , N. A. , Rocco , V. P. , Spinazze , P. G. , Hemrick‐Luecke , S. K. , Thompson , L. K. , Evans , D. C. , Rasmussen , K. , Koger , D. , Lodge , D. , Martin , L. J. , Shaw , J. , Threlkeld , P. G. and Wong , D. T. 2006 . Advances toward new antidepressants beyond SSRIs: 1‐Aryloxy‐3‐piperidinyl‐propan‐2‐ols with dual 5‐HT1A receptor antagonism/SSRI activities. part 5 . Bioorg. Med. Chem. Lett. , 16 : 2347 – 2351 .
   PubMedGoogle Scholar
• López‐Rodríguez , M. L. , Morcillo , M. J. , Fernández , E. , Benhamú , B. , Tejada , I. , Ayala , D. , Viso , A. , Campillo , M. , Pardo , L. , Delgado , M. , Manzanares , J. and Fuentes , J. A. 2005 . Synthesis and structure–activity relationships of a new model of arylpiperazines, 8: Computational simulation of ligand–receptor interaction of 5‐HT1AR agonists with selectivity over α1‐adrenoceptors . J. Med. Chem. , 48 : 2548 – 2558 .
   PubMed Web of Science ®Google Scholar
• Valderrama , J. A. and Valderrama , C. 1997 . Studies on quinones, part 30: Synthesis of benzo[b]thiophene‐4,7‐quinones . Synth. Commun. , 27 ( 12 ) : 2143 – 2157 .
   Web of Science ®Google Scholar
• Pessoa‐Mahana , C. D. , Valderrama , J. A. , Olmos , M. G. , Espinoza , O. A. , Pessoa‐Mahana , H. , Rojas de Arias , A. , Nakayama , H. , Torres , S. and Miret , J. 2002 . Studies on quinones, part 36: Synthesis and trypanocidal activity of 2‐alkoxy carbonylbenzo[b]thiophene‐4,7‐quinones . Heterocycl. Commun. , 8 ( 2 ) : 135 – 140 .
   Web of Science ®Google Scholar
• Prusis , P. , Dambrova , M. , Andrianov , V. , Rozhkov , E. , Semenikhina , V. , Piskunova , I. , Ongwae , E. , Lundstedt , T. , Kalvinsh , I. and Wikberg , J. E. S. 2004 . Synthesis and quantitative structure–activity relationship of hydrazones of N‐amino‐N′‐hydroxyguanidine as electron acceptors for xanthine oxidase . J. Med. Chem. , 47 ( 12 ) : 3105 – 3110 .
   PubMed Web of Science ®Google Scholar
• Allan , G. M. , Parsons , A. F. and Pons , J. F. 2002 . Tandem radical cyclization and translocation approaches to biologically important mitomycin ring systems . Synlett. , 9 : 1431 – 1434 .
   Google Scholar