New method for the synthesis of N-β-N-nitroso-(p-aminobenzoic acid ethyl ester) -2,3,4-tri-O-acetyl-L-arabinopyranosylamine and prediction of potential biological activity"

Author: Miranda Gongadze
Keywords: L-arabinose, Nitroso (N=O)
Annotation:

The synthesis of Nitroso (N=O) group containing carbohydrate derivatives and study of their biological activity is a promising research direction to obtain new type biologically and pharmacologically active compounds. The goal of present investigation consist in synthesis of nitroso group (N=O) containing L-arabinopyranosylamine by new method and determination of biological activity potential. The formation of N-β-(p-aminobenzoicacid ethylesteryl)-L-arabinopyranosylamine (2) by condensation of L-arabinose (1) with p-aminobenzoic acid ethyl ester in 50% methanol, in the present of acetic acid was studied at the first stage. Acetylation of (2) gave product (3), followed by nitrozylation to synthesis of N-β-N-nitroso-(p-amino- benzoicacid ethylesteryl)-2,3,4,6-tetra-O-acetyl- L-arabinopyranosylamine (4). The nitrozilation was performed by a new method. The Reactions proceeds accor- dingto the following scheme: OH H OH H H O H2N COOC2H5 H O CH3OH OAc H 32H O NaNO2H O HO OH H,OH HO OH (CH CO) O, CH3COONa OAc H H 1 2 N H H COOC2H5 Py; 00 AcO H OAc N 3 H CH2CI2 p-TSA AcO H OAc 4 N=O COOC2H5 5 N COOC2H5 The structures of obtainedcompounds were established by physical-chemical methods of analysis. L-With the help of computer program PASS Online basedon the analysis of structure activity- relationshipswide range of possible biological activityand toxic / side effectsfor synthesized L-arabinopyranosylamineshas been determined.