title: Synthesis and cytotoxicity evaluation of aryl triazolic derivatives and their hydroxymethine homologues against B16 melanoma cell line.
abstract: In this manuscript we describe synthesis and cytotoxicity evaluation of some triazolic derivatives against B16 melanoma cell line. For this purpose, we transformed a set of aromatic aldehydes into terminal alkynes, using Besthmann-Ohira reagent, and we made the corresponding hydroxymethyl homologated alkynes by an acetylene Grignard reagent. These generated two sets of alkynes were then subjected to a copper(I)-catalyzed alkyne-azide cycloaddition reaction (CuAAC) using a solid-supported catalyst (Amberlyst A-21 CuI), with a third set composed of organic azides. Synthesized triazoles were then tested in vitro against B16 melanoma cell line. Amongst them, compounds a1b1 (R(1) = p-nitrophenyl, R(2) = benzyl), a4b1 (R(1) = naphthyl, R(2) = benzyl) and a4b5 (R(1) = naphthyl, R(2) = (R/S)- dioxolane) showed the best activity against B16 melanoma cells, with IC50 of 5.12, 3.89 and 6.60 μM respectively.
authors.affiliation: CNRS UMR8258, INSERM U1022, Unité de Technologies Chimiques et Biologiques pour la Santé, Equipe SEISAD, Ecole Nationale Supérieure de Chimie de Paris (Chimie ParisTech), PSL Research University, 11 rue Pierre & Marie Curie, Paris, 75005, France.
authors.forename: Shiva
authors.initials: S
authors.lastname: Kalhor-Monfared
authors.affiliation: CNRS UMR8258, INSERM U1022, Unité de Technologies Chimiques et Biologiques pour la Santé, Equipe SEISAD, Ecole Nationale Supérieure de Chimie de Paris (Chimie ParisTech), PSL Research University, 11 rue Pierre & Marie Curie, Paris, 75005, France.
authors.forename: Claire
authors.initials: C
authors.lastname: Beauvineau
authors.affiliation: CNRS UMR8258, INSERM U1022, Faculté de Pharmacie, Université Paris Descartes, Sorbonne Paris Cité, 4 avenue de l'Observatoire, 75006, Paris, France.
authors.forename: Daniel
authors.initials: D
authors.lastname: Scherman
authors.affiliation: CNRS UMR8258, INSERM U1022, Unité de Technologies Chimiques et Biologiques pour la Santé, Equipe SEISAD, Ecole Nationale Supérieure de Chimie de Paris (Chimie ParisTech), PSL Research University, 11 rue Pierre & Marie Curie, Paris, 75005, France. Electronic address: christian.girard@enscp.fr.
authors.forename: Christian
authors.initials: C
authors.lastname: Girard
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D008546:Melanoma, Experimental / Q000473:pathology*; D008697:Methane / Q000737:chemistry; D051379:Mice; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D014230:Triazoles; D008697:Methane
keywords: Alkyne; Anticancer; B16 melanoma; Click chemistry; Triazole