FIELD: medicine, pharmaceutics.
SUBSTANCE: invention relates to field of bioorganic and medical chemistry, in particular, to method of obtaining novel potentially biologically active derivative of betulonic acid - methyl ester of 3-oxo-3'-(nitromethyl)-4'-(chlormethyl)-spiro[lupane-2,1'-cyclopenbtane]-28-oic acid. Compound represents methyl alcohol of betulonic acid, containing at carbon atom C-2 spirocyclopentane fragment with vicinal (cis-, trans-configuration) CH2NO2- and CH2Cl-substituents. Method of its obtaining lies in obtaining at first stage methyl ester of 2,2-diallyl-3-oxolupane-28-oic acid (DBK) by interaction of methyldihydrobetulonate (BK) with great molar excess of potassium tret-butilate (ButOK) and allyl bromide with molar reagent ratio - BK: ButOK:allylbromide=1:3-4 (mainly 4):2, in dimethoxyetane at room temperature with further isolation and purification of obtained product by method of column chronomatography on SiO2, which is later subjected to radical cycloisomerisation under impact of Fe(NO3)3·9H2O, FeCl3, with molar ratio 2,2-diallyl-derivative and iron salts - DBK: Fe(NO3)3·9H2O:FeCl3=1:1.2:1.5 with boiling of reagents in tetrahydrofurane for 3-7 hours, mainly 3 hours, with further purification of obtained methyl ester of 3-oxo-3'-(nitromethyl)-4'-(chlormethyl)-spiro[lupane-2,1'-cyclopenbtane]-28-oic acid by method of column chromatography on SiO2 chromatography on SiO2. Output of compound in terms of methyldihydrobetulonate constituted 40%.
EFFECT: method is characterised by selectivity, simplicity of carrying out experiment and application of cheap, environmentally friendly and non-toxic reagents Fe(NO3)3-9H2O, FeCl3 which do not lead to formation of harmful and by- products.
1 cl, 4 ex
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Authors
Dates
2012-04-27—Published
2010-11-08—Filed