The synthesis in excellent yields of 1-acyl-3-furfuryl-1-phenylthioureas (I) (R - aryl) by reacting at t ≤ 10° 3-furfuryl-1-phenylthiourea (II), prepd. in situ from furfurylamine and Ph isothiocyanate, with arom. or heterocyclic acyl chlorides in pyridine soln. is described. The 1-acylthioureas I rearranged in high yields to 3-acylthioureas (III) (R = aryl) by treatment with sodium hydroxide in heterogeneous phase. The 1,3-diacyl-3-furfuryl-1-phenylthioureas (IV) (R = aryl C) were obtained in satisfactory yields by treatment of II with 2 mol of acyl chloride as in the case of 1-monoacylation. The thiourea II prepd. in situ reacted with iodomethane in DMF soln. and in the presence of sodium hydride to give in high yield the S-Me deriv., namely the Me ester of N-phenyl-1-furfurylaminethiocarboximidic acid. Some acylthioureas I and IV showed a platelet antiaggregating activity in vitro superior or comparable to that of acetylsalicylic acid. The 1,3-diacylthiourea IV (R = 4-MeOC6H4) exhibited an appreciable anticonvulsant activity in mice, some compds. (I and IV) showed moderate competitive antiacetylcholine and H1-antihistamine effects in vitro.
1-Acyl-, 3-acyl- and 1,3-diacyl-3-furfuryl-1-phenylthioureas with platelet antiaggregating and other activities.
RANISE, ANGELO;BONDAVALLI, FRANCESCO;BRUNO, OLGA;SCHENONE, SILVIA;
1991-01-01
Abstract
The synthesis in excellent yields of 1-acyl-3-furfuryl-1-phenylthioureas (I) (R - aryl) by reacting at t ≤ 10° 3-furfuryl-1-phenylthiourea (II), prepd. in situ from furfurylamine and Ph isothiocyanate, with arom. or heterocyclic acyl chlorides in pyridine soln. is described. The 1-acylthioureas I rearranged in high yields to 3-acylthioureas (III) (R = aryl) by treatment with sodium hydroxide in heterogeneous phase. The 1,3-diacyl-3-furfuryl-1-phenylthioureas (IV) (R = aryl C) were obtained in satisfactory yields by treatment of II with 2 mol of acyl chloride as in the case of 1-monoacylation. The thiourea II prepd. in situ reacted with iodomethane in DMF soln. and in the presence of sodium hydride to give in high yield the S-Me deriv., namely the Me ester of N-phenyl-1-furfurylaminethiocarboximidic acid. Some acylthioureas I and IV showed a platelet antiaggregating activity in vitro superior or comparable to that of acetylsalicylic acid. The 1,3-diacylthiourea IV (R = 4-MeOC6H4) exhibited an appreciable anticonvulsant activity in mice, some compds. (I and IV) showed moderate competitive antiacetylcholine and H1-antihistamine effects in vitro.
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