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

doi:10.1021/acs.joc.0c01291

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

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

13 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 language	English
Pages (from-to)	10994-11005
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	85
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.0c01291
Publication status	Published - 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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10.1021/acs.joc.0c01291

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

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).",

author = "Joshi, {Dirgha Raj} and Yohan Seo and Yunkyung Heo and Park, {So Hyeon} and Yechan Lee and Wan Namkung and Ikyon Kim",

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 {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = aug,

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doi = "10.1021/acs.joc.0c01291",

language = "English",

volume = "85",

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AU - Joshi, Dirgha Raj

AU - Seo, Yohan

AU - Heo, Yunkyung

AU - Park, So Hyeon

AU - Lee, Yechan

AU - Namkung, Wan

AU - Kim, Ikyon

N1 - 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.

PY - 2020/8/21

Y1 - 2020/8/21

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

Abstract

Bibliographical note

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