Novel hederagenin-triazolyl derivatives as potential anti-cancer agents

被引：51

作者：

Rodriguez-Hernandez, Diego ^{[1
,2
]}

Demuner, Antonio J. ^{[1
]}

Barbosa, Luiz C. A. ^{[1
,2
]}

Heller, Lucie ^{[3
]}

Csuk, Rene ^{[3
]}

机构：

[1] Univ Fed Vicosa, Dept Chem, Av PH Rolfs S-N, BR-36570900 Vicosa, MG, Brazil

[2] Univ Fed Minas Gerais, Dept Chem, Av Pres Antonio Carlos 6627,Campus Pampulha, BR-31270901 Belo Horizonte, MG, Brazil

[3] Univ Halle Wittenberg, Organ Chem, Kurt Mothes Str 2, D-06120 Halle, Saale, Germany

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2016年 / 115卷

关键词：

Sapindus saponaria; Huisgen 1,3-dipolar cycloaddition; Hederagenin derivatives; SRB assay; MEDICINAL CHEMISTRY; ANTITUMOR-ACTIVITY; BIOFILM FORMATION; ACID-DERIVATIVES; LACTONES; SAPONINS; ANALOGS; PLANT; CYTOTOXICITY; APOPTOSIS;

D O I：

10.1016/j.ejmech.2016.03.018

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel aryl-1H-1,2,3-triazol-4-yl methylester and amide derivatives of the natural product hederagenin was synthesized aiming to develop new antitumor agents, using Huisgen 1,3-dipolar cycloaddition reactions, with yields between 35% and 95%. The structures of all derivatives (2-31) Were confirmed by MS, IR, H-1 NMR and C-13 NMR spectroscopic data. The cytotoxic activities of all compounds were screened against a panel of six human cancer cell lines using SRB assay. It was found that most of the compounds displayed higher levels of antitumor activities as compared to parent hederagenin. Compounds 4, 8 and 15 were the most potent against all human cancer cell lines. Furthermore, compound 11 was the most cytotoxic against cell HT29 showing EC50 = 1.6 mu M and a selectivity index of 5.4. (C) 2016 Elsevier Masson SAS. All rights reserved.

引用

页码：257 / 267

页数：11

共 37 条

[1] C-13 NMR-SPECTROSCOPY OF OLEANANE TRITERPENOIDS
AGRAWAL, PK
JAIN, DC
[J]. PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 1992, 24 : 1 - 90
[2] Albiero A.L.M., 2001, ACTA FARM BONAER, V20, P169
[3] Albiero ALM, 2002, J ETHNOPHARMACOL, V82, P41, DOI 10.1016/S0378-8741(02)00094-6
[4] [Anonymous], 2011, ESPECTROSCOPIA INFRA
[5] A quantum chemical and chemometric study of sesquiterpene lactones with cytotoxicity against tumor cells
Arantes, Francisco F. P.
Barbosa, Luiz C. A.
Maltha, Celia R. A.
Demuner, Antonio J.
Fidencio, Paulo H.
Carneiro, Jose Walkimar M.
[J]. JOURNAL OF CHEMOMETRICS, 2011, 25 (08) : 401 - 407
[6] Barbosa LCD, 2004, Z NATURFORSCH C, V59, P803
[7] Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents
Chen, Haijun
Gao, Yu
Wang, Ailan
Zhou, Xiaobin
Zheng, Yunquan
Zhou, Jia
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 648 - 655
[8] Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives
Csuk, Rene
Niesen-Barthel, Anja
Schaefer, Renate
Barthel, Alexander
Al-Harrasi, Ahmed
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 700 - 711
[9] Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives
Csuk, Rene
Schwarz, Stefan
Siewert, Bianka
Kluge, Ralph
Stroehl, Dieter
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) : 5356 - 5369
[10] Synthesis and plant growth regulatory activity of 6α,7β-dihydroxyvouacapan-17β-oic acid derivatives
Demuner, AJ
Barbosa, LCA
Veloso, DP
Howarth, OW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (01) : 61 - 66

← 1 2 3 4 →