Domino [4 + 2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer N-Fused Polycycles.
Dirgha Raj JoshiYohan SeoYunkyung HeoSo-Hyeon ParkYechan LeeWan NamkungIkyon KimPublished in: The Journal of organic chemistry (2020)
A highly efficient synthetic route to new quinone-indolizine hybrids was accomplished from quinones and N-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).
Keyphrases
- highly efficient
- induced apoptosis
- endothelial cells
- prostate cancer
- cell cycle arrest
- squamous cell carcinoma
- wastewater treatment
- molecular dynamics
- molecular docking
- induced pluripotent stem cells
- signaling pathway
- oxidative stress
- pluripotent stem cells
- locally advanced
- cell proliferation
- endoplasmic reticulum stress
- radiation therapy
- low cost