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

A statistically significant QSAR model describing the bioactivity of bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-carbonitriles (N = 41, n = 8, R2 = 0.824, R2cv = 0.724, F = 18.749, s2 = 0.0018) was obtained employing CODESSA-Pro software. The bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-c...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2015-01, Vol.89, p.835-843
Main Authors: Girgis, Adel S., Saleh, Dalia O., George, Riham F., Srour, Aladdin M., Pillai, Girinath G., Panda, Chandramukhi S., Katritzky, Alan R.
Format: Article
Language:English
Subjects:
4-Piperidone
4H-Pyrano[3,2-c]pyridine-3-carbonitrile
Animals
Biological Assay
Bronchodilation
Bronchodilator Agents - chemical synthesis
Bronchodilator Agents - chemistry
Bronchodilator Agents - pharmacology
Guinea Pigs
Linear Models
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Pyrans - pharmacology
Pyridines - chemical synthesis
Pyridines - chemistry
Pyridines - pharmacology
QSAR
Quantitative Structure-Activity Relationship
Software
Ylidenemalononitrile
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Summary:A statistically significant QSAR model describing the bioactivity of bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-carbonitriles (N = 41, n = 8, R2 = 0.824, R2cv = 0.724, F = 18.749, s2 = 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. [Display omitted] A statistically significant QSAR model describing the bioactivity of bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-carbonitriles. •Pyrano[3,2-c]pyridines were synthesized in a facile synthetic approach.•Bronchodilation properties of the pyrano[3,2-c]pyridines were reported.•Many of the compounds synthesized exhibit promising activity compared with theophylline.•A significant QSAR model was explored describing the bronchodilation activity.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2013.12.032