An efficient synthesis of some new NSAIDs prodrugs viz., (S)-ethyl 2-[(S)-2-(4-isobutylphenyl)propanamido]-4-methylpentanoate (1), (S)-ethyl 2-[(R)-2-(4-isobutylphenyl)propanamido]-4-methylpentanoate (2), (S)-dimethyl 2-[2-(2,3-dimethylphenylamino)benzamido]-succinate (3) and (RS)-methyl-2-(2-(2,6-dichloro-3-methylphenylamino)benzamido)butanoate (4) with high purity were carried out by the amidation of RS-ibuprofen, mefenamic acid and meclofenamic acid with methyl ester and ethyl ester of amino acids L-leucine, L-aspartic acid and DL-2-aminobutyric acid. The products formed were confirmed by IR, 1H NMR, 13C NMR, HR MS (1-4) and single crystal X-ray crystallography analysis (2-4). Compound (2) crystallizes in orthorhombic space group P212121 with unit cell dimensions a = 5.1931 (2) Å, b = 10.0031 Å, c = 41.0764 (11) Å, = = = 90°, V = 2133.80 (12) Å3, Z = 4. Compound (3) crystallizes in hexagonal space group P65 with unit cell dimensions a = 11.4965 (3) Å, b = 11.4965 (3) Å, c = 26.5323 (12) Å, = = 90°, = 120°, V = 3036.94 (18) Å3, Z = 6. Compound (4) crystallizes in triclinic space group Pi with unit cell dimensions a = 8.7969 (3) Å, b = 10.6307 (3) Å, c = 11.8469 (4) Å, = 76.724 (3)°, = 89.066 (3)°, = 66.169 (2)°, V = 982.70 (5) Å3, Z = 2.
قسم البحث
مجلة البحث
Asian J. Chem.
تصنيف البحث
1
عدد البحث
Vol.26, No.16
موقع البحث
http://dx.doi.org/10.14233/ajchem.2014.16949
سنة البحث
2014
المشارك في البحث
ملخص البحث