title: Synthesis and SAR studies of potent H(+)/K(+)-ATPase inhibitors of quinazolinone-Schiff's base analogues.
abstract: A series of quinazolinone derived Schiff base derivatives 7-36 were synthesized and characterized by analytical and spectroscopic techniques. The synthesized analogues were screened for their in vitro H(+)/K(+)-ATPase inhibition. Most of the compounds showed excellent activity, compared to that of omeprazole, a reference drug. In particular, hydroxy and methoxy derivatives 13-24 were the most active compounds possessing a significant increase for different substituents on the benzene ring thus, contributing positively to gastric H(+)/K(+)-ATPase inhibition. Preliminary structure-activity relationship revealed that the compounds 13-24 with electron donating moiety (OH, OCH3) were found to be excellent activity and compounds 9-12 and 25-36 with electron withdrawing moiety (Cl, F, NO2 and Br) were found to be least antiulcer agents.
authors.affiliation: Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, Karnataka, India. Electronic address: rakeshasg@gmail.com.
authors.forename: K P
authors.initials: KP
authors.lastname: Rakesh
authors.affiliation: Department of Chemistry, Pooja Bhagavath Memorial Mahajana Education Centre, Mysuru 570016, Karnataka, India.
authors.forename: C S
authors.initials: CS
authors.lastname: Shantharam
authors.affiliation: Department of Studies in Biotechnology, University of Mysore, Manasagangotri, Mysuru 570 006, Karnataka, India.
authors.forename: H M
authors.initials: HM
authors.lastname: Manukumar
mesh_terms: D000818:Animals; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017506:H(+)-K(+)-Exchanging ATPase / Q000378:metabolism*; D015394:Molecular Structure; D052999:Quinazolinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D012756:Sheep; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D052999:Quinazolinones; D012545:Schiff Bases; D017506:H(+)-K(+)-Exchanging ATPase
keywords: Electronic effect; H(+)/K(+)-ATPase activity; Quinazolinones; Schiff’s bases