Synthetic transformations of higher terpenoids. XXVI. 16-acetylaminomethyllabdanoids and their cytotoxicity |
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Authors: | Yu V Kharitonov E E Shul’ts M M Shakirov M A Pokrovsky A G Pokrovsky G A Tolstikov |
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Institution: | 1.Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences,Novosibirsk,Russia;2.Novosibirsk State University,Novosibirsk,Russia |
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Abstract: | Coupling of methyl 16-aminomethyllambertianate with N-Boc-protected ω-amino acids resulted in 16-(N-Boc-aminononan)- and 16-(N-Boc-aminoundecan)amidomethyllabdanoids. Interaction of methyl aminomethyllambertianate with bicyclo2.2.1]hept-5-en-2,3-dicarboxylic
acid anhydride led to the amide of bicyclo2.2.1]heptan-1,2-dicarboxylic acid with a labdanoid substituent. Reaction of methyl
16-aminomethyllambertianate with chloroacetyl chloride resulted in methyl 16-(chloroacetylaminomethyl)lambertianate; coupling
of the latter with methyl esters of amino acids gave the corresponding amides of methyl lambertianate. The compounds obtained
were more cytotoxic toward CEM-13, MT-4, and U-937 tumor cell lines as compared with lambertianic acid; the dose inhibiting
tumor cell viability by 50% (CCID50) of the more active compounds was 3.9–9.9 μM. |
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