10-N-heterocylic aryl-isoxazole-amides (AIMs) have robust anti-tumor activity against breast and brain cancer cell lines and useful fluorescence properties

Matthew J. Weaver, Sascha Stump, Michael J. Campbell, Donald S. Backos, Chun Li, Philip Reigan, Earle Adams, Howard D. Beall, Nicholas R. Natale

Research output: Contribution to journalArticlepeer-review

Abstract

A novel series of anthracenyl-isoxazole amide (AIM) antitumor agents containing N-heterocycles in the 10 position (N-het) were synthesized using palladium cross-coupling. The unique steric environment of the N-het-AIMs required individual optimization in each case. Lanthanide mediated double activation was used to couple the dimethylamino pyrrole moiety, required for antitumor action. Robust antitumor activity was observed against breast and brain cancer cell lines. The compounds were docked with the c-myc oncogene promoter sequence, which adopts a G4 quadruplex DNA conformation, and represents the working hypothesis for biological action. The N-het-AIMs have useful fluorescence properties, allowing for observation of their distribution within tumor cells.

Original languageEnglish
Article number115781
JournalBioorganic and Medicinal Chemistry
Volume28
Issue number22
DOIs
StatePublished - Nov 15 2020

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