TY - JOUR
T1 - Polycyclic N‐hetero compounds. XLIII. Syntheses and properties of 2‐substituted 1‐acetoxy‐6‐acetyl‐5,6‐dihydro‐4H‐imidazo[1′,2′:1,6]‐pyrimido[5,4‐d][1]benzazepines viaN‐(6,7‐dihydro‐5H‐pyrimido[5,4‐d]‐[1]benzazepin‐4‐yl)amino acids and their analogous mesoionic compounds, and their related compounds as a series of potential blood platelet aggregation inhibitors
AU - Nagamatsu, Tomohisa
AU - Hantani, Yoshiji
AU - Sasaki, Kenji
AU - Ohtomo, Hiromi
AU - Nakayama, Taiji
AU - Hirota, Takashi
PY - 1993/1/1
Y1 - 1993/1/1
N2 - A study of the cyclization method by heating of N‐(6,7‐dihydro‐5H‐pyrimido[5,4‐d][1]benzazepin‐4‐yl)amino acids 3a‐h, 6, and 9a,b with excess acetic anhydride for the preparation of 2‐substituted 1‐acetoxy‐6‐acetyl‐5,6‐dihydro‐4H‐imidazo[1,2′:1,6]pyrirnido[5,4‐d][1]benzazepines 4a‐h and tetra‐ and penta‐cyclic mesoionic compounds 7 and 10a,b has been made. In addition, a tetracyclic mesoionic compound having a sulfur atom on the skeleton, 5,6‐dihydro‐4H‐thiazolo[3′,2′:1,6]pyrimido[5,4‐d][1]benzazepiniurn‐1‐one (12) was similarly prepared by treatment of 2‐(6,7‐dihydro‐5H‐pyrimido[5,4‐d][1]benzazepm‐4‐ylthio)acetic acid (11) with excess acetic anhydride. Their inhibitory activities against collagen‐induced aggregation of rabbit blood platelets in vitro were also investigated, and some heterocycles exhibited from a two‐ to a four‐fold more potent activity as compared with aspirin.
AB - A study of the cyclization method by heating of N‐(6,7‐dihydro‐5H‐pyrimido[5,4‐d][1]benzazepin‐4‐yl)amino acids 3a‐h, 6, and 9a,b with excess acetic anhydride for the preparation of 2‐substituted 1‐acetoxy‐6‐acetyl‐5,6‐dihydro‐4H‐imidazo[1,2′:1,6]pyrirnido[5,4‐d][1]benzazepines 4a‐h and tetra‐ and penta‐cyclic mesoionic compounds 7 and 10a,b has been made. In addition, a tetracyclic mesoionic compound having a sulfur atom on the skeleton, 5,6‐dihydro‐4H‐thiazolo[3′,2′:1,6]pyrimido[5,4‐d][1]benzazepiniurn‐1‐one (12) was similarly prepared by treatment of 2‐(6,7‐dihydro‐5H‐pyrimido[5,4‐d][1]benzazepm‐4‐ylthio)acetic acid (11) with excess acetic anhydride. Their inhibitory activities against collagen‐induced aggregation of rabbit blood platelets in vitro were also investigated, and some heterocycles exhibited from a two‐ to a four‐fold more potent activity as compared with aspirin.
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U2 - 10.1002/jhet.5570300140
DO - 10.1002/jhet.5570300140
M3 - Article
AN - SCOPUS:0027402285
VL - 30
SP - 233
EP - 240
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
SN - 0022-152X
IS - 1
ER -