Synthetic transformation of higher terpenoids 31. Synthesis of 1,2,3-triazoIyI-containing furan labdanoids and studies of their cytotoxic activity

摘要

16-(l-R-l,2,3-Triazol-4-ylethyl)-, 16-(l-R-l,2,3-triazol-4-ylmethoxymethyl)-, and 16-{2-(l-R-l,2,3-triazol-4-yl)-l-[(l-R-l,2,3-triazol-4-ylmethoxy)ethyl]}-substituted derivatives of methyl lambertianate were synthesized by 1,3-cycloaddition of labdanoid alkynes with azides. The compounds obtained possess considerable cytotoxicity toward the human tumor ceil lines CEM-13, MT-4, and U-937. The most active compound, methyl 16-(2-{2-[(l-benzyl-lif-l,2,3-triazol-4-yl)acetyl]niran-3-yl}ethyl)lambertianate, was found to inhibit the viability of the tumor cells by 50% (CCID_(50)) in the concentration of 7-12 nmol L~(-1).