Synthesis, bioassay, and QSAR study of bronchodilatory active 4 H-pyrano[3,2-c]pyridine-3-carbonitriles

Abstract

A statistically significant QSAR model describing the bioactivity of bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-carbonitriles (N Combining double low line 41, n Combining double low line 8, R2 Combining double low line 0.824, R2cv Combining double low line 0.724, F Combining double low line 18.749, s2 Combining double low line 0.0018) was obtained employing CODESSA-Pro software. The bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-carbonitriles 17-57 were synthesized through a facile approach via reaction of 1-alkyl-4-piperidones 1-4 with ylidenemalononitriles 5-16 in methanol in the presence of sodium. The bronchodilation properties of 17-57 were investigated in vitro using isolated guinea pig tracheal rings pre-contracted with histamine (standard method) and compared with theophylline (standard reference). Most of the compounds synthesized exhibit promising bronchodilation properties especially, compounds 25 and 28.