Synthesis and in vitro Calcium Antagonist Activity of 4‐Aryl‐7,7‐dimethyl/1,7,7‐trimethyl‐1,2,3,4,5,6,7,8‐octahydroquinazoline ‐2,5‐dione Derivatives.

Abstract

Fused pyrimidine derivativesFused pyrimidine derivatives R 0515 Synthesis and in vitro Calcium Antagonist Activity of 4-Aryl-7,7-dimethyl/ 1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione Derivatives. -Title compounds (IV) (25 examples) are prepared by one-pot condensation of ureas (I), aromatic aldehydes (II) and cyclohexanedione (III) under strongly acidic conditions according to the Biginelli reaction. Their calcium antagonist activity is tested in vitro on isolated rat ileum and lamb carotid artery. Compounds (IVd) and (IVe) are the most active derivatives. -(YARIM, M.; SARAC*, S.; KILIC, F. S.; EROL, K.; Farmaco 58 (2003) 1, 17-24; Dep. Pharm. Chem., Fac. Pharm., Hacettepe Univ., TR-06100 Ankara, Turk.; Eng.) -F. Santoso 22-159

KF/Al2O3 Promoted Aza-Michael Addition of 4-Aryl-7,7-Dimethyloctahydro-Quinazolinones to α, β-Ethylenic Compounds

“…Preparation of 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazo-line-2-one/thione-5-ones; general procedure The reaction of benzaldehyde (10 mmol) 1 with urea/thiourea (12 mmol) and 5,5-dimethylcyclohexane-1,3-dione (10 mmol) in the presence of H 2 SO 4 (10% mmol) as catalyst in ethanol (10 mL) at 80 °C for 8 hours produced 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-one/thione-5-ones. After the reaction was completed (monitored by TLC), pure product was obtained from the crude product by filtration and recrystallisation to afford: 4-Phenyl -7,7-dimethyl-1,2,3,4,5,6,7,8- 2,3,4,5,6,7, 6, 174.6, 148.7, 143.3, 128.5, 127.5, 126.4, 108.1, 52.2, 52.1, 49.8, 32.2, 28.8, 26.7 6.33;N,9.78. Found: C,67.28;H,6.42 N,9.76%.…”

“…2, 173.6, 152.9, 151.2, 141.2, 139.5, 129.4, 127.8, 110.2, 58.4, 53.5, 50.8, 48.4, 39.6, 33.7, 32.9, 28.7, 27.4, 1,2,3,4,5,6,7,8-octahydroquinazoline-2,5- 194.2, 173.6, 154.8, 152.3, 140.2, 134.7, 129.6, 128.7, 109.4, 59.3, 51.7, 52.6, 44.6, 40.7, 31.5, 33.2, 29.5, 27.2 : C,61.46;H,5.93;N,7.17. Found: C,61.27;H,5.99;N,2,3,4,5,6,7, 13 C NMR (CDCl 3 ): δ = 196. 3, 172.9, 152.4, 148.6, 147.9, 144.3, 128.6, 127.2, 107.2, 62.4, 52.6, 51.3, 43.5, 40.9, 33.4, 32.7, 29.2, 27.4 : C,59.84;H,5.78;N,10.47.…”

“…3, 172.9, 152.4, 148.6, 147.9, 144.3, 128.6, 127.2, 107.2, 62.4, 52.6, 51.3, 43.5, 40.9, 33.4, 32.7, 29.2, 27.4 : C,59.84;H,5.78;N,10.47. Found: C,59.69;H,5.83;N,2,3,4,5,6,7,…”

“…Calcd for C 20 H 23 N 2 ClO 4 : C,61.46;H,5.93;N,7.17. Found: C,61.57;H,5.98;N,2,3,4,5,6,7, 1.11 (s,3H,CH 3 ), 0.94 (t, J = 14.8 Hz, 3H, CH 3 ) , 0.90 (s, 3H, CH 3 ). 13 C NMR (CDCl 3 ): δ = 192.…”

“…13 C NMR (CDCl 3 ): δ = 192. 6, 171.6, 153.8, 146.3, 144.1, 128.8, 128.2, 128.3, 109.8, 63.7, 59.7, 50.6, 48.9, 40.1, 32.9, 31.9, 30.4, 29.5, 27.5, 19.6, 14.9 2,3,4,5,6,7, 13 C NMR (CDCl 3 ): δ = 194. 2, 154.8, 152.7, 145.3, 133.2, 129.4, 118.0, 115.2, 112.3, 60.9, 50.5, 48.3, 40.2, 33.1, 29.8, 26.9, 15.6 2,3,4,5,6,7, 13 C NMR (CDCl 3 ): δ = 196.0, 175.0, 162.…”