The prepn. of 2-(diethylamino)-7-ethoxychromone (I, X = O, R = R1 = H, R22N = Et2N) and a variety of related compds. is reported. Thus, 3-EtOC6H4OH cyclocondensed with R22NCOCH2CO2Et (R22N = Et2N, piperidino) in the presence of POCl3 to give I (X = O, R = R1 = H, R22N = Et2N, piperidino). Treating the latter compds. with P2S5 gave I (X = S) or with CH2(CN)2 gave I [X = C(CN)2]. Nitration of I (X = O, R = R1 = H, R22N = Et2N) with (HNO3-H2SO4) gave I (X = O, R = R1 = NO2, R22N = Et2N), whereas, formylation with Cl2CHOMe-TiCl4 gave a mixt. of I (X = O, R = CHO, R1 = H, R22N = Et2N) and I (X = O, R = H, R1 = CHO, R22N = Et2N). A test of I for their in vitro inhibition of human blood platelet aggregation showed I (X = O, R = R1 = H, R22N = Et2N) was the most active.
Synthesis and antiplatelet activity of 2-(diethylamino)-7-ethoxychromone and related compounds
MAZZEI, MAURO;DI BRACCIO, MARIO;BALBI, ALESSANDRO;
1990-01-01
Abstract
The prepn. of 2-(diethylamino)-7-ethoxychromone (I, X = O, R = R1 = H, R22N = Et2N) and a variety of related compds. is reported. Thus, 3-EtOC6H4OH cyclocondensed with R22NCOCH2CO2Et (R22N = Et2N, piperidino) in the presence of POCl3 to give I (X = O, R = R1 = H, R22N = Et2N, piperidino). Treating the latter compds. with P2S5 gave I (X = S) or with CH2(CN)2 gave I [X = C(CN)2]. Nitration of I (X = O, R = R1 = H, R22N = Et2N) with (HNO3-H2SO4) gave I (X = O, R = R1 = NO2, R22N = Et2N), whereas, formylation with Cl2CHOMe-TiCl4 gave a mixt. of I (X = O, R = CHO, R1 = H, R22N = Et2N) and I (X = O, R = H, R1 = CHO, R22N = Et2N). A test of I for their in vitro inhibition of human blood platelet aggregation showed I (X = O, R = R1 = H, R22N = Et2N) was the most active.
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