Novel triazoles of 3-acetylbetulin and betulone as anticancer agents

Abstract

The CuAAC reaction of azides and acetylenic triterpenes was used for synthesis of new triazoles of 3-acetylbetulin and betulone. The triazole derivatives were evaluated for their anticancer activity in vitro against amelanotic melanoma C-32, ductal carcinoma T47D and glioblastoma SNB-19 cell lines. 28-[1-(3’-Deoxythymidine-5’-yl)-1H-1,2,3-triazol-4-yl]carbonylbetulone 6e exhibited a significant IC50 value (0.17 µM) against the human glioblastoma SNB-19 cell line, an almost 5-fold higher potency while compared with reference cisplatin.

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

“…Other triazole-natural compound hybrids, triterpene derivative-linked 1,2,3-triazole moieties were prepared and their anticancer potentials were investigated on the selected cancer cells such as C-32, T47D, and SNB-19 using the WST-1 assay. 55 Hybrid derivative 11 (Fig. 3) displayed a significant IC 50 value (0.17 µM) toward the human glioblastoma SNB-19 cell line, which was nearly 5-fold higher that the value of the reference drug cisplatin.…”

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

“…Bebenek et al . have reported the preparation of novel 1,2,3‐ triazoles of pentacyclic triterpenes 3‐acetylbetulin and betulone 86 and 87 by use of the click reaction of organic azides and acetylenic triterpenes 84 , 85 .…”

Oxidation of a wood extractive betulin to biologically active oxo-derivatives using supported gold catalysts

“…The 3-oxo derivative of betulin betulone and its derivatives, exhibiting antitumor, antiinflammatory, aniparasitic, and anti-HIV properties, also demonstrate in vitro cytotoxic activity against different cancer cell lines. [10][11][12][13][14][15][16][17][18][19][20][21][22] Recent studies indicate a clear demand for betulone as a building block for creating effective anticancer agents with minimal side effects. [20][21][22] Currently, the main method of synthesis of betulin oxoderivatives is its oxidation.…”

“…[10][11][12][13][14][15][16][17][18][19][20][21][22] Recent studies indicate a clear demand for betulone as a building block for creating effective anticancer agents with minimal side effects. [20][21][22] Currently, the main method of synthesis of betulin oxoderivatives is its oxidation. The work of Csuk et al 23 described the formation of betulinic acid via betulinic aldehyde by oxidation of betulin with a mixture comprising TEMPO (2,2,6,6tetramethylpiperidine-1-oxyl)-NaClO 2 -NaOCl at 35°C with 92% yield.…”