title: Synthesis and biological evaluation of antiplatelet 2-aminochromones.
abstract: The synthesis and biological evaluation of a series of antiplatelet 2-morpholinylchromones has been described. Modification of the C-7 phenylmethoxy group of 8-methyl-7-(phenylmethoxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one (2) has led to the discovery of a series of 7-[(amino-ethyl)oxy]-8-methyl derivatives which are potent inhibitors of ADP-induced platelet aggregation. Several members of this class proved active in preventing platelet-dependent thrombus formation in the dog, including 8-methyl-7-[2-(4-methyl-1-piperazinyl)ethoxy]-2-(4- morpholinyl)-4H-1-benzopyran-4-one (39) which was devoid of hemodynamic effects at the effective antithrombotic dose.
authors.affiliation: Upjohn Laboratories, Upjohn Company, Kalamazoo, Michigan 49001.
authors.forename: J
authors.initials: J
authors.lastname: Morris
authors.forename: D G
authors.initials: DG
authors.lastname: Wishka
authors.forename: A H
authors.initials: AH
authors.lastname: Lin
authors.forename: W R
authors.initials: WR
authors.lastname: Humphrey
authors.forename: A L
authors.initials: AL
authors.lastname: Wiltse
authors.forename: R B
authors.initials: RB
authors.lastname: Gammill
authors.forename: T M
authors.initials: TM
authors.lastname: Judge
authors.forename: S N
authors.initials: SN
authors.lastname: Bisaha
authors.forename: N L
authors.initials: NL
authors.lastname: Olds
authors.forename: C S
authors.initials: CS
authors.lastname: Jacob
mesh_terms: D000244:Adenosine Diphosphate / Q000037:antagonists & inhibitors; D000818:Animals; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004285:Dogs; D005260:Female; D006801:Humans; D008297:Male; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010974:Platelet Aggregation / Q000187:drug effects*; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
chemical_list: D002867:Chromones; D009025:Morpholines; D010879:Piperazines; D010975:Platelet Aggregation Inhibitors; C082308:8-methyl-7-(2-(4-methyl-1-piperazinyl)ethoxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one; D000244:Adenosine Diphosphate