ABSTRACT
Synthesis of biaryl-containing macrocycles has been carried out through a four-step approach comprising two Ugi four component reactions and a Suzuki-Miyaura macrocyclization. This protocol allowed the synthesis of 12- and 14-membered macrocycles. Cytotoxic activity evaluation showed that some of the molecules were effective against leukemia, glioblastoma and lung cancer cell lines (IC50 = 4.0, 5.9 and 7.6, respectively).
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Biphenyl Compounds/chemical synthesis , Biphenyl Compounds/pharmacology , Macrocyclic Compounds/chemical synthesis , Macrocyclic Compounds/pharmacology , Antineoplastic Agents/chemistry , Biphenyl Compounds/chemistry , Cell Line , Cell Proliferation/drug effects , Crystallography, X-Ray , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Macrocyclic Compounds/chemistry , Models, Molecular , Molecular Structure , Structure-Activity RelationshipABSTRACT
A phenylethynyl Fischer carbene complex was used as a traceless directing group for the regioselective cycloaddition of dithiolethiones to arylacetylene, which constitutes the first synthesis of E-dithiafulvene thione or dithioesters.
ABSTRACT
[reaction: see text] Tricyclic 4-ethyl-5-thioxo-3H,5H-bis[1,2]dithiolo[3,4-d][4,3-b]pyrrol-3-one and monocyclic 3H-1,2-dithiole-3-thione derivatives reacted with Fischer carbene complexes, giving 1,3-dithiin dithioortho esters through insertion of the carbenic carbon into the S-S bond next to the thiocarbonyl function of the substrate.