[Synthetic transformations of higher terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and theirs cytotoxicity].
Condensation of methyl 16-aminomethyllambertianate with N-Boc-omega-amino acids leads smoothly to 16-(N-Boc-aminononan)- and 16-(N-Boc-aminoundecan)amidomethyllabdanoids. The amide of bicyclo[2.2.1]heptan-1,2-dicarbocylic acid with a labdanoid substituent was obtained under the reaction of methyl aminomethyllambertianate with bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride. Intereaction of methyl 16-aminomethyllambertianate with chloroacetyl chloride leads to methyl 16-(chloroacetylaminomethyl)lambertianate; condensation of this compound with amino acid methyl ethers the corresponding amides of methyl lambertianate was obtained. The resulting compounds are more (compared with lambertianic acid) cytotoxicity in the cell lines CEM-13, MT-4 and U-937 with an CCID50 concentration of 3.9-9.9 microM.
Iu V
IuV
Kharitonov
É É
ÉÉ
Shul'ts
M M
MM
Shakirov
M A
MA
Pokrovskiĭ
A G
AG
Pokrovskiĭ
G A
GA
Tolstikov
D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D006801:Humans; D020298:U937 Cells
D003603:Cytotoxins; D004224:Diterpenes