10-Alkoxy-anthracenyl-isoxazole analogs have sub-micromolar activity against a Glioblastoma multiforme cell line

Nathan S. Duncan, Michael J. Campbell, Donald S. Backos, Chun Li, Kevin C. Rider, Sascha Stump, Matthew J. Weaver, Mariusz P. Gajewski, Howard D. Beall, Philip Reigan, Nicholas R. Natale

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A series of 10-alkoxy-Anthryl-isoxazole-pyrrole-doubletails (RO-AIMs) were synthesized using a crown ether assisted nucleophilic aromatic substitution followed by a modified Schotten-Baumann reaction. The novel RO-AIMs described here exhibit robust growth inhibition for the human SNB19 CNS glioblastoma cell line, and biphenyl analog 8c had activity in the nanomolar regime, which represents the most efficacious compound in the AIM series to date. Computational modeling for RO-AIMs binding in a ternary complex with c-myc quadruplex DNA and its helicase DHX36 is presented which represents our current working hypothesis.

Original languageEnglish
Article number116911
JournalBioorganic and Medicinal Chemistry
Volume69
DOIs
StatePublished - Sep 1 2022

Keywords

  • Anti-tumor
  • Isoxazole
  • Pyrrole
  • Quadruplex DNA
  • Synthesis

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