title: [2+2+2] Cycloadditions of siloxy alkynes with 1,2-diazines: from reaction discovery to identification of an antiglycolytic chemotype.
abstract: Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf=trifluoromethanesulfonyl, TIPS=triisopropylsilyl.
authors.affiliation: Chicago Tri-Institutional Center for Chemical Methods and Library Development, Department of Chemistry, The University of Chicago, Chicago, IL 60637 (USA).
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Montavon
authors.forename: Yunus E
authors.initials: YE
authors.lastname: Türkmen
authors.forename: Noumaan A
authors.initials: NA
authors.lastname: Shamsi
authors.forename: Christopher
authors.initials: C
authors.lastname: Miller
authors.forename: Chintan S
authors.initials: CS
authors.lastname: Sumaria
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
authors.forename: Sergey A
authors.initials: SA
authors.lastname: Kozmin
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction / Q000379:methods*; D006019:Glycolysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes
keywords: cycloaddition; inhibitor; polycycles; siloxyalkynes; synthetic methods