Preparation of novel ring-A fused azole derivatives of betulin and evaluation of their cytotoxicity

Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

“…Thus, a synthesis of novel 2,3-seco-triterpenoids and triterpenoids bearing five-membered ring A, all displaying cytotoxicity, was published (Scheme 1) [42]. The compounds were prepared on the basis of betulone ( 4 ) that is modified to the 2-oxime derivative of betulonic acid ( 5 ) by a several steps procedure [42,43]. Further structural modification of 5 (Scheme 1) resulted in a subsequent synthesis of the compounds 6 – 9 [42], representing the most cytotoxic structures of this series of compounds [42].…”

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.…”

Synthesis, characterization and cytotoxic activity evaluation of ginsengdiol oxidation and nitrogen hybrid derivatives

“…22 Interestingly, the azole compounds of betulinic acid were extremely sensitive to HCT116 cells and had a low effect on human normal cells. 23 Mallavadhani et al found that pyrimidine compounds possessed general inhibitory activity in breast cancer cells during the structural modification of oleanolic acid, and its activity was superior to the positive drug etoposide. 24 Meanwhile, it was reported that the oxidation and A ring-opening products of betulinic acid exhibited good activity in inhibiting tumor proliferation, while the oxidation product of PD and the ring-opening product of A ring can inhibit HIV and HCV protease.…”