title: Diaryl and heteroaryl sulfides: synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents.
abstract: A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
authors.affiliation: Department of Chemistry, University of California , Irvine, California 92697-2025, United States.
authors.forename: Ivelina M
authors.initials: IM
authors.lastname: Yonova
authors.forename: Charlotte A
authors.initials: CA
authors.lastname: Osborne
authors.forename: Naomi S
authors.initials: NS
authors.lastname: Morrissette
authors.forename: Elizabeth R
authors.initials: ER
authors.lastname: Jarvo
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D006801:Humans; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D061986:MCF-7 Cells / Q000737:chemistry* / Q000187:drug effects*; D015394:Molecular Structure; D013434:Sulfenic Acids / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D002712:Chlorides; D007093:Imidazoles; D007659:Ketones; D013434:Sulfenic Acids; D013438:Sulfhydryl Compounds; D013440:Sulfides