Domino [4 + 2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer N-Fused Polycycles

Dirgha Raj Joshi, Yohan Seo, Yunkyung Heo, So Hyeon Park, Yechan Lee, Wan Namkung, Ikyon Kim

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)10994-11005
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number16
DOIs
Publication statusPublished - 2020 Aug 21

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2017R1A2A2A05069364, NRF-2018R1A6A1A03023718, NRF-2019R1I1A1A01061117, and NRF-2020R1A2C2005961) for generous financial support. This research was supported (in part) by Yonsei University Research Fund (Post Doc. Researcher Supporting Program) of 2019 (project no.: 2019-12-0013).

Publisher Copyright:
Copyright © 2020 American Chemical Society.

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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