Dataset Information

Synthesis, Selected Transformations, and Biological Activity of Alkoxy Analogues of Lepidilines A and C.

ABSTRACT: Condensation of diacetyl monooxime with formaldimines derived from alkoxyamines in glacial acetic acid at room temperature leads to corresponding 2-unsubstituted imidazole N-oxides bearing an alkoxy substituent at the N(1) atom of the imidazole ring. Subsequent O-benzylation afforded, depending on the type of alkylating agent, either symmetric or nonsymmetric alkoxyimidazolium salts considered as structural analogues of naturally occurring imidazole alkaloids, lepidilines A and C. Some of the obtained salts were tested as precursors of nucleophilic heterocyclic carbenes (NHCs), which in situ reacted with elemental sulfur to give the corresponding N-alkoxyimidazole-2-thiones. The cytotoxic activity of selected 4,5-dimethylimidazolium salts bearing either two benzyloxy or benzyloxy and 1-adamantyloxy groups at N(1) and N(3) atoms was evaluated against HL-60 and MCF-7 cell lines using the MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) assay. Notably, in two cases of alkoxyimidazolium salts, no effect of the counterion exchange (Br- ? PF6-) on the biological activity was observed.

SUBMITTER: Mloston G

PROVIDER: S-EPMC7560456 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Synthesis, Selected Transformations, and Biological Activity of Alkoxy Analogues of Lepidilines A and C.

Mlostoń Grzegorz G Celeda Małgorzata M Poper Wiktor W Kowalczyk Mateusz M Gach-Janczak Katarzyna K Janecka Anna A Jasiński Marcin M

Materials (Basel, Switzerland) 20200921 18

Condensation of diacetyl monooxime with formaldimines derived from alkoxyamines in glacial acetic acid at room temperature leads to corresponding 2-unsubstituted imidazole <i>N</i>-oxides bearing an alkoxy substituent at the N(1) atom of the imidazole ring. Subsequent <i>O</i>-benzylation afforded, depending on the type of alkylating agent, either symmetric or nonsymmetric alkoxyimidazolium salts considered as structural analogues of naturally occurring imidazole alkaloids, lepidilines A and C. ...[more]

PMID: 32967232

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Dataset Information

Synthesis, Selected Transformations, and Biological Activity of Alkoxy Analogues of Lepidilines A and C.

Publications

Synthesis, Selected Transformations, and Biological Activity of Alkoxy Analogues of Lepidilines A and C.

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