Novel hederagenin-triazolyl derivatives as potential anti-cancer agents. 2016

Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
Department of Chemistry, Universidade Federal de Viçosa, Av. P. H. Rolfs, s/n, CEP 36570-900, Viçosa, MG, Brazil; Department of Chemistry, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos 6627, Campus Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil.

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, (1)H NMR and (13)C 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 μM and a selectivity index of 5.4.

UI MeSH Term Description Entries
D009828 Oleanolic Acid A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. Oleanol,Hederins,Oleanane Triterpenes,Triterpenes, Oleanane
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines

Related Publications

Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
August 2013, European journal of medicinal chemistry,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
June 2018, European journal of medicinal chemistry,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
May 2018, European journal of medicinal chemistry,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
January 2019, Medicinal chemistry (Shariqah (United Arab Emirates)),
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
September 2021, Journal of agricultural and food chemistry,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
April 2005, Archiv der Pharmazie,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
April 2021, Drug research,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
October 2021, Bioorganic chemistry,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
August 2012, Journal of enzyme inhibition and medicinal chemistry,
Diego Rodríguez-Hernández, and Antonio J Demuner, and Luiz C A Barbosa, and Lucie Heller, and René Csuk
November 2012, European journal of medicinal chemistry,
Copied contents to your clipboard!