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[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.

SUBMITTER: Montavon TJ

PROVIDER: S-EPMC3996828 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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[2+2+2] Cycloadditions of siloxy alkynes with 1,2-diazines: from reaction discovery to identification of an antiglycolytic chemotype.

Montavon Timothy J TJ Türkmen Yunus E YE Shamsi Noumaan A NA Miller Christopher C Sumaria Chintan S CS Rawal Viresh H VH Kozmin Sergey A SA

Angewandte Chemie (International ed. in English) 20131107 51

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. ...[more]

PMID: 24346942

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