One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities

Shi Qiang Li; Wei Yan; Liu Jun He; Ming Zhang; Dian Yong Tang; Hong Yu Li; Zhong Zhu Chen; Zhi Gang Xu

doi:10.1039/d1qo01694f

One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities

Shi Qiang Li
, Wei Yan
, Liu Jun He
, Ming Zhang
, Dian Yong Tang
, Hong Yu Li
, Zhong Zhu Chen
, Zhi Gang Xu

Pharmacology and Toxicology

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

8 Scopus citations

Abstract

A post-Ugi/diastereoselective cascade reaction was developed to construct naturally existing spiroindolines via a facile and metal-free one-pot protocol. During the construction, a new C-C bond was formed through a selective 5-exo-dig indole cyclization on the propiolamide; and a new C-N bond was diastereoselectively formed which controlled the configuration of three chiral centers simultaneously. Screening data of several difficult-to-inhibit cancer cell lines demonstrated that (±)-6d could strongly inhibit colon cell U87 proliferation with an IC50 value of 0.19 ± 0.04 μM. Taken together, our research provided a novel and robust protocol towards the synthesis of spiroindolines and revealed their potential application as anti-cancer agents in diverse human cancer cell lines. This journal is

Original language	English (US)
Pages (from-to)	682-686
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	9
Issue number	3
DOIs	https://doi.org/10.1039/d1qo01694f
State	Published - Feb 7 2022

ASJC Scopus subject areas

Organic Chemistry

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10.1039/d1qo01694f

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title = "One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities",

abstract = "A post-Ugi/diastereoselective cascade reaction was developed to construct naturally existing spiroindolines via a facile and metal-free one-pot protocol. During the construction, a new C-C bond was formed through a selective 5-exo-dig indole cyclization on the propiolamide; and a new C-N bond was diastereoselectively formed which controlled the configuration of three chiral centers simultaneously. Screening data of several difficult-to-inhibit cancer cell lines demonstrated that (±)-6d could strongly inhibit colon cell U87 proliferation with an IC50 value of 0.19 ± 0.04 μM. Taken together, our research provided a novel and robust protocol towards the synthesis of spiroindolines and revealed their potential application as anti-cancer agents in diverse human cancer cell lines. This journal is ",

author = "Li, \{Shi Qiang\} and Wei Yan and He, \{Liu Jun\} and Ming Zhang and Tang, \{Dian Yong\} and Li, \{Hong Yu\} and Chen, \{Zhong Zhu\} and Xu, \{Zhi Gang\}",

note = "Funding Information: The authors would like to thank the Science and Technology Research Program of Chongqing Municipal Education Commission (CXQT19029 and KJZD-M201801301), Science \& Technology Department of Sichuan Province (2017FZ0084) and the Natural Science Foundation Project of CQ CSTSC (cstc2018jszx-cyzdX0023 and cstc2021jcyj-bsh0233). We would also like to thank Ms H. Z. Liu and J. Xu for obtaining the HRMS and NMR data. Publisher Copyright: {\textcopyright} the Partner Organisations.",

year = "2022",

month = feb,

day = "7",

doi = "10.1039/d1qo01694f",

language = "English (US)",

volume = "9",

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journal = "Organic Chemistry Frontiers",

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AU - Li, Shi Qiang

AU - Yan, Wei

AU - He, Liu Jun

AU - Zhang, Ming

AU - Tang, Dian Yong

AU - Li, Hong Yu

AU - Chen, Zhong Zhu

AU - Xu, Zhi Gang

N1 - Funding Information: The authors would like to thank the Science and Technology Research Program of Chongqing Municipal Education Commission (CXQT19029 and KJZD-M201801301), Science & Technology Department of Sichuan Province (2017FZ0084) and the Natural Science Foundation Project of CQ CSTSC (cstc2018jszx-cyzdX0023 and cstc2021jcyj-bsh0233). We would also like to thank Ms H. Z. Liu and J. Xu for obtaining the HRMS and NMR data. Publisher Copyright: © the Partner Organisations.

PY - 2022/2/7

Y1 - 2022/2/7

N2 - A post-Ugi/diastereoselective cascade reaction was developed to construct naturally existing spiroindolines via a facile and metal-free one-pot protocol. During the construction, a new C-C bond was formed through a selective 5-exo-dig indole cyclization on the propiolamide; and a new C-N bond was diastereoselectively formed which controlled the configuration of three chiral centers simultaneously. Screening data of several difficult-to-inhibit cancer cell lines demonstrated that (±)-6d could strongly inhibit colon cell U87 proliferation with an IC50 value of 0.19 ± 0.04 μM. Taken together, our research provided a novel and robust protocol towards the synthesis of spiroindolines and revealed their potential application as anti-cancer agents in diverse human cancer cell lines. This journal is

AB - A post-Ugi/diastereoselective cascade reaction was developed to construct naturally existing spiroindolines via a facile and metal-free one-pot protocol. During the construction, a new C-C bond was formed through a selective 5-exo-dig indole cyclization on the propiolamide; and a new C-N bond was diastereoselectively formed which controlled the configuration of three chiral centers simultaneously. Screening data of several difficult-to-inhibit cancer cell lines demonstrated that (±)-6d could strongly inhibit colon cell U87 proliferation with an IC50 value of 0.19 ± 0.04 μM. Taken together, our research provided a novel and robust protocol towards the synthesis of spiroindolines and revealed their potential application as anti-cancer agents in diverse human cancer cell lines. This journal is

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JO - Organic Chemistry Frontiers

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One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities

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