Domino [4 + 2] Annulation Access to Quinone–Indolizine Hybrids: Anticancer <i>N</i>-Fused Polycycles
Dirgha Raj Joshi, Yohan Seo, Yunkyung Heo, So-Hyeon Park, Yechan Lee, W. Namkung, Ikyon Kim
Abstract
-substituted pyrrole-2-carboxaldehydes via a domino Michael addition-aldol condensation-aromatization sequence through which the central pyridine ring was constructed in atom-economical and environment-friendly manner. Post modification of the resulting products was also demonstrated, enabling further expansion of this heterocyclic chemical space. Biological evaluation of the quinone-indolizine hybrids revealed potent anticancer effects in human prostate adenocarcinoma cells (PC-3) and oral adenosquamous carcinoma cells (CAL-27).
Topics & Concepts
ChemistryIndolizineAromatizationQuinoneAnnulationPyridinePyrroleDominoStereochemistryRing (chemistry)Combinatorial chemistryBenzopyransMoietyMedicinal chemistryOrganic chemistryCatalysisSynthesis and Reactivity of HeterocyclesSynthesis and pharmacology of benzodiazepine derivativesSynthesis and bioactivity of alkaloids