The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells

Fifteen novel glycyrrhetinic acid derivatives containing a nitrogen heterocycle at C-30 and with different A-ring substituents were designed and synthesized. All of these derivatives have improved antiproliferative effects against human HL-60 leukemia cells. Compounds with a cyano-enone functionalit...

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Autores principales: Gao, Yuan, Guo, Xin, Li, Xiaojing, Liu, Dan, Song, Dandan, Xu, Ye, Sun, Ming, Jing, Yongkui, Zhao, Linxiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264780/
https://www.ncbi.nlm.nih.gov/pubmed/20657452
http://dx.doi.org/10.3390/molecules15064439
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author Gao, Yuan
Guo, Xin
Li, Xiaojing
Liu, Dan
Song, Dandan
Xu, Ye
Sun, Ming
Jing, Yongkui
Zhao, Linxiang
author_facet Gao, Yuan
Guo, Xin
Li, Xiaojing
Liu, Dan
Song, Dandan
Xu, Ye
Sun, Ming
Jing, Yongkui
Zhao, Linxiang
author_sort Gao, Yuan
collection PubMed
description Fifteen novel glycyrrhetinic acid derivatives containing a nitrogen heterocycle at C-30 and with different A-ring substituents were designed and synthesized. All of these derivatives have improved antiproliferative effects against human HL-60 leukemia cells. Compounds with a cyano-enone functionality on the A-ring exhibit greater growth inhibitory effects, compared to those with a 2-hydroxymethylene-3-keto, an isoxazole, or a 2-cyano-3-keto group. N-(2-cyano-3,11-dioxoolean-1,12-dien-30-yl)-4-piperidyl piperidine (9b) was found to be two-fold more potent than methyl 2-cyano-3,11-dioxooleana-1,12- dien-30-oate (CDODO-Me-11).
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spelling pubmed-62647802018-12-04 The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells Gao, Yuan Guo, Xin Li, Xiaojing Liu, Dan Song, Dandan Xu, Ye Sun, Ming Jing, Yongkui Zhao, Linxiang Molecules Article Fifteen novel glycyrrhetinic acid derivatives containing a nitrogen heterocycle at C-30 and with different A-ring substituents were designed and synthesized. All of these derivatives have improved antiproliferative effects against human HL-60 leukemia cells. Compounds with a cyano-enone functionality on the A-ring exhibit greater growth inhibitory effects, compared to those with a 2-hydroxymethylene-3-keto, an isoxazole, or a 2-cyano-3-keto group. N-(2-cyano-3,11-dioxoolean-1,12-dien-30-yl)-4-piperidyl piperidine (9b) was found to be two-fold more potent than methyl 2-cyano-3,11-dioxooleana-1,12- dien-30-oate (CDODO-Me-11). MDPI 2010-06-21 /pmc/articles/PMC6264780/ /pubmed/20657452 http://dx.doi.org/10.3390/molecules15064439 Text en © 2010 by the authors; licensee MDPI, Basel, Switzerland. This article is an Open Access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Gao, Yuan
Guo, Xin
Li, Xiaojing
Liu, Dan
Song, Dandan
Xu, Ye
Sun, Ming
Jing, Yongkui
Zhao, Linxiang
The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells
title The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells
title_full The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells
title_fullStr The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells
title_full_unstemmed The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells
title_short The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells
title_sort synthesis of glycyrrhetinic acid derivatives containing a nitrogen heterocycle and their antiproliferative effects in human leukemia cells
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264780/
https://www.ncbi.nlm.nih.gov/pubmed/20657452
http://dx.doi.org/10.3390/molecules15064439
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