An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity

We report a “green chemistry”-based Ugi cascade reaction to furnish a series of 2,5-diketopiperazines (through nucleophilic attack of amides upon ketones in Ugi adducts) at moderate-to-good yields. Investigation with the MTT assay revealed compound (±) 5c to exhibit potent anticancer activities agai...

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Detalles Bibliográficos
Autores principales: Li, Jie, Huang, Jiu Hong, Wang, Jing Ya, Xu, Zhi Gang, Chen, Zhong Zhu, Lei, Jie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9678023/
https://www.ncbi.nlm.nih.gov/pubmed/36425196
http://dx.doi.org/10.1039/d2ra04958a
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author Li, Jie
Huang, Jiu Hong
Wang, Jing Ya
Xu, Zhi Gang
Chen, Zhong Zhu
Lei, Jie
author_facet Li, Jie
Huang, Jiu Hong
Wang, Jing Ya
Xu, Zhi Gang
Chen, Zhong Zhu
Lei, Jie
author_sort Li, Jie
collection PubMed
description We report a “green chemistry”-based Ugi cascade reaction to furnish a series of 2,5-diketopiperazines (through nucleophilic attack of amides upon ketones in Ugi adducts) at moderate-to-good yields. Investigation with the MTT assay revealed compound (±) 5c to exhibit potent anticancer activities against acute myeloid leukaemia (MV411; IC(50) = 1.7 μM) and acute T lymphocyte leukaemia (Jurkat; IC(50) = 5.7 μM) cell lines.
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spelling pubmed-96780232022-11-23 An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity Li, Jie Huang, Jiu Hong Wang, Jing Ya Xu, Zhi Gang Chen, Zhong Zhu Lei, Jie RSC Adv Chemistry We report a “green chemistry”-based Ugi cascade reaction to furnish a series of 2,5-diketopiperazines (through nucleophilic attack of amides upon ketones in Ugi adducts) at moderate-to-good yields. Investigation with the MTT assay revealed compound (±) 5c to exhibit potent anticancer activities against acute myeloid leukaemia (MV411; IC(50) = 1.7 μM) and acute T lymphocyte leukaemia (Jurkat; IC(50) = 5.7 μM) cell lines. The Royal Society of Chemistry 2022-11-21 /pmc/articles/PMC9678023/ /pubmed/36425196 http://dx.doi.org/10.1039/d2ra04958a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Li, Jie
Huang, Jiu Hong
Wang, Jing Ya
Xu, Zhi Gang
Chen, Zhong Zhu
Lei, Jie
An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
title An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
title_full An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
title_fullStr An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
title_full_unstemmed An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
title_short An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
title_sort intramolecular hydrogen bond-promoted “green” ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9678023/
https://www.ncbi.nlm.nih.gov/pubmed/36425196
http://dx.doi.org/10.1039/d2ra04958a
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