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.
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.
Okuda
Kensuke
K
Gifu Pharmaceutical University, Gifu 501-1196, Japan. okuda@gifu-pu.ac.jp
Zhang
Ying-Xue
YX
Ohtomo
Hiromi
H
Hirota
Takashi
T
Sasaki
Kenji
K
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
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