ArticleMolecules (Basel, Switzerland)2013
1,2,3-triazole-substituted oleanolic Acid derivatives: synthesis and antiproliferative activity.
Article in Molecules (Basel, Switzerland), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed.
- The Use of Zidovudine Pharmacophore in Multi-Target-Directed Ligands for AIDS Therapy.Molecules (Basel, Switzerland) · 2022Review
- Bile-Acid-Appended Triazolyl Aryl Ketones: Design, Synthesis, In Vitro Anticancer Activity and Pharmacokinetics in Rats.Molecules (Basel, Switzerland) · 2021Article
- Pentacyclic Triterpenoids with Nitrogen-Containing Heterocyclic Moiety, Privileged Hybrids in Anticancer Drug Discovery.Molecules (Basel, Switzerland) · 2021Review
- Synthesis and Antiproliferative Activity of Novel Heterocyclic Glycyrrhetinic Acid Derivatives.Molecules (Basel, Switzerland) · 2019Article
- Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry.Molecules (Basel, Switzerland) · 2018Article
- Antiprotozoal Activity of Triazole Derivatives of Dehydroabietic Acid and Oleanolic Acid.Molecules (Basel, Switzerland) · 2017Article
- Cytotoxic conjugates of betulinic acid and substituted triazoles prepared by Huisgen Cycloaddition from 30-azidoderivatives.PloS one · 2017Article
- Crystal structures of two triazola-dioxola-benzena-cyclo-nona-phanes.Acta crystallographica. Section E, Crystallographic communications · 2015Article
- Synthesis, antiproliferative and antifungal activities of 1,2,3-triazole-substituted carnosic Acid and carnosol derivatives.Molecules (Basel, Switzerland) · 2015Article
- MicroRNA let-7b suppresses human gastric cancer malignancy by targeting ING1.Cancer gene therapy · 2015Article
- Nucleostemin regulates proliferation and migration of gastric cancer and correlates with its malignancy.International journal of clinical and experimental medicine · 2015Article
- MicroRNA-126 regulates migration and invasion of gastric cancer by targeting CADM1.International journal of clinical and experimental pathology · 2015Article
- The up-regulation of miR-300 in gastric cancer and its effects on cells malignancy.International journal of clinical and experimental medicine · 2015Article
- Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid.Molecules (Basel, Switzerland) · 2014Article
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4 authors.
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Abstract
Hybrid compounds are relevant products when searching for structure-activity relationships of natural products. Starting from the naturally occurring triterpene oleanolic acid, alkyl esters were prepared and treated with different aromatic azides using click chemistry to produce hybrid compounds. Some 18 new oleanolic acid derivatives were synthesized and the structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new derivatives was evaluated towards normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), promyelocytic leukemia (HL-60), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. The alkyne esters 1 and 3 showed activity on all cell lines but without selectivity (19.6-23.1 μM and 14.1-56.2 μM, respectively), their respective methyl esters were inactive. Compounds with a benzene and p-anisole attached to the triazole ring, showed no antiproliferative effect. Introduction of a chlorine atom into the benzene ring (compound 9) elicited a selective effect against AGS cells (IC50 value: 8.9 μM). The activity was lost when the COOH function at C-28 was methylated. Better antiproliferative effect was found for compounds 11 and 15 bearing a p-toluenesulphonyl group, with values in the range of 10.8-47.1 μM and 11.5-22.2 μM, respectively. The effect, however, was not associated with selectivity.
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