title: Synthesis of novel polysubstituted (2SR,4RS)-2-heteroaryltetrahydro-1,4-epoxy-1-benzazepines and cis-2-heteroaryl-4-hydroxytetrahydro-1H-1-benzazepines as antiparasitic agents.
abstract: New series of polysubstituted (2SR,4RS)-2-heteroaryltetrahydro-1,4-epoxy-1-benzazepines and cis-2-heteroaryl-4-hydroxytetrahydro-1H-1-benzazepines were designed and synthesized in moderate to high yields using a three-step procedure from ortho-allylanilines. Their antiparasitic activity was evaluated against the extracellular and intracellular forms of Trypanosoma cruzi and Leishmania (Leishmania) infantum parasites. Their cytotoxicity was also determined on Vero and THP-1 mammalian cells. Many of the tested compounds inhibited significantly the growth of extracellular forms of T. cruzi and L. (L.) infantum without showing cytotoxicity on Vero and HTP-1 cells. Only compounds 10h and 14f demonstrated good activity against amastigotes of T. cruzi, but none was able to inhibit the growth of L. (L.) infantum amastigotes.
authors.affiliation: Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Santander, Colombia.
authors.forename: María C
authors.initials: MC
authors.lastname: Blanco
authors.affiliation: Centro de Investigación de Enfermedades Tropicales, Departamento de Ciencias Básicas, Escuela de Medicina, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Santander, Colombia.
authors.forename: Patricia
authors.initials: P
authors.lastname: Escobar
authors.affiliation: Centro de Investigación de Enfermedades Tropicales, Departamento de Ciencias Básicas, Escuela de Medicina, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Santander, Colombia.
authors.forename: Sandra M
authors.initials: SM
authors.lastname: Leal
authors.affiliation: Laboratorio de RMN, Grupo de Productos Naturales, Departamento de Química, Universidad de los Andes, Mérida 5101, Venezuela.
authors.forename: Alí
authors.initials: A
authors.lastname: Bahsas
authors.affiliation: Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain.
authors.forename: Justo
authors.initials: J
authors.lastname: Cobo
authors.affiliation: Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain.
authors.forename: Manuel
authors.initials: M
authors.lastname: Nogueras
authors.affiliation: Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Santander, Colombia. Electronic address: apalma@uis.edu.co.
authors.forename: Alirio
authors.initials: A
authors.lastname: Palma
mesh_terms: D000818:Animals; D000977:Antiparasitic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D004305:Dose-Response Relationship, Drug; D018314:Leishmania infantum / Q000187:drug effects*; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D013329:Structure-Activity Relationship; D014349:Trypanosoma cruzi / Q000187:drug effects*; D014709:Vero Cells
chemical_list: D000977:Antiparasitic Agents; D001552:Benzazepines
keywords: (2SR,4RS)-2-heteroaryltetrahydro-1,4-epoxy-1-benzazepines; Antiparasitic activity; Cytotoxicity; Leishmania (Leishmania) infantum; Trypanosoma cruzi; cis-2-Heteroaryltetrahydro-1H-1-benzazepin-4-ols