[Synthetic transformations of higher terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and theirs cytotoxicity]

Iu V Kharitonov; É É Shul'ts; M M Shakirov; M A Pokrovskiĭ; A G Pokrovskiĭ; G A Tolstikov

doi:10.1134/s1068162011060082

[Synthetic transformations of higher terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and theirs cytotoxicity]

Bioorg Khim. 2012 Jan-Feb;38(1):127-36. doi: 10.1134/s1068162011060082.

[Article in Russian]

Authors

Iu V Kharitonov, É É Shul'ts, M M Shakirov, M A Pokrovskiĭ, A G Pokrovskiĭ, G A Tolstikov

PMID: 22792716
DOI: 10.1134/s1068162011060082

Abstract

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.

Publication types

English Abstract
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cytotoxins* / chemical synthesis
Cytotoxins* / chemistry
Cytotoxins* / pharmacology
Diterpenes* / chemical synthesis
Diterpenes* / chemistry
Diterpenes* / pharmacology
Dose-Response Relationship, Drug
Humans
U937 Cells

Substances

Cytotoxins
Diterpenes