title: Polycyclic N-heterocyclic compounds. Part 62: Reaction of N-(quinazolin-4-yl)amidine derivatives with hydroxylamine hydrochloride and anti-platelet aggregation activity of the products.
abstract: The reactions of N-(5,6,7,8-tetrahydroquinazolin-4-yl)amidines and their amide oximes with hydroxylamine hydrochloride gave abnormal cyclization products via a ring cleavage of pyrimidine component accompanied with a ring closure of 1,2,4-oxadiazole to give N-[2-([1,2,4]oxadiazol-5-yl)cyclohexen-1-yl]formamide oximes. Similarly, N-(quinazolin-4-yl)amidines reacted with hydroxylamine hydrochloride gave the same results. The evaluation of inhibitory activities against platelet aggregation in vitro is also described to show one derivative has potent activity.
authors.affiliation: Gifu Pharmaceutical University, Gifu 501-1196, Japan. okuda@gifu-pu.ac.jp
authors.forename: Kensuke
authors.initials: K
authors.lastname: Okuda
authors.forename: Ying-Xue
authors.initials: YX
authors.lastname: Zhang
authors.forename: Hiromi
authors.initials: H
authors.lastname: Ohtomo
authors.forename: Takashi
authors.initials: T
authors.lastname: Hirota
authors.forename: Kenji
authors.initials: K
authors.lastname: Sasaki
mesh_terms: D000578:Amidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D019811:Hydroxylamine / Q000737:chemistry*; D008297:Male; D015394:Molecular Structure; D010974:Platelet Aggregation / Q000187:drug effects*; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011799:Quinazolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011817:Rabbits; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000578:Amidines; D006571:Heterocyclic Compounds; C549739:N-(5,6,7,8-tetrahydroquinazolin-4-yl)amidine; C549740:N-(quinazolin-4-yl)-amidine; D010975:Platelet Aggregation Inhibitors; D011083:Polycyclic Compounds; D011799:Quinazolines; D019811:Hydroxylamine