title: Synthesis, bioassay, and QSAR study of bronchodilatory active 4H-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 = 41, n = 8, R(2) = 0.824, R(2)cv = 0.724, F = 18.749, s(2) = 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.
authors.affiliation: Pesticide Chemistry Department, National Research Centre, Dokki, Cairo 12622, Egypt.
authors.forename: Adel S
authors.initials: AS
authors.lastname: Girgis
authors.affiliation: Pharmacology Department, National Research Centre, Dokki, Cairo 12622, Egypt.
authors.forename: Dalia O
authors.initials: DO
authors.lastname: Saleh
authors.affiliation: Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo, Egypt.
authors.forename: Riham F
authors.initials: RF
authors.lastname: George
authors.affiliation: Therapeutical Chemistry Department, National Research Centre, Dokki, Cairo 12622, Egypt.
authors.forename: Aladdin M
authors.initials: AM
authors.lastname: Srour
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA; Department of Chemistry, University of Tartu, Ravila 14a, Tartu 50411, Estonia.
authors.forename: Girinath G
authors.initials: GG
authors.lastname: Pillai
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: Chandramukhi S
authors.initials: CS
authors.lastname: Panda
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA; Department of Chemistry, King Abdulaziz University, Jeddah 21589, Saudi Arabia. Electronic address: katritzky@chem.ufl.edu.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D000818:Animals; D001681:Biological Assay; D001993:Bronchodilator Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006168:Guinea Pigs; D016014:Linear Models; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D012984:Software
chemical_list: D001993:Bronchodilator Agents; D011714:Pyrans; D011725:Pyridines
keywords: 4-Piperidone; 4H-Pyrano[3,2-c]pyridine-3-carbonitrile; Bronchodilation; QSAR; Ylidenemalononitrile