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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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1-Acyl-, 3-acyl- and 1,3-diacyl-3-furfuryl-1-phenylthioureas with platelet antiaggregating and other activities.

The synthesis in excellent yields of 1-acyl-3-furfuryl-1-phenylthioureas 2 by reacting at t less than or equal to 10 degrees C 3-furfuryl-1-phenylthiourea 1, prepared in situ from furfurylamine and phenyl isothiocyanate, with aromatic or heterocyclic acyl chlorides in pyridine solution is described. 1-Acylthioureas 2 rearranged in high yields to 3-acylthioureas 3 by treatment with sodium hydroxide in heterogeneous phase. 1,3-Diacyl-3-furfuryl-1-phenylthioureas 4 were obtained in satisfactory yields by treatment of 1 with two moles of acyl chloride as in the case of 1-monoacylation. The thiourea 1 prepared in situ reacted with iodomethane in dimethylformamide solution and in the presence of sodium hydride to give in high yield the S-methyl derivative, namely the methyl ester of N-phenyl-1-furfurylaminethiocarboximidic acid. Some acylthioureas 2 and 4 showed a platelet antiaggregating activity in vitro superior or comparable to that of acetylsalicylic acid. The 1,3-diacylthiourea 4 c exhibited an appreciable anticonvulsant activity in mice and some compounds 2 and 4 moderate competitive antiacetylcholine and H1-antihistamine effects in vitro.[1]

References

  1. 1-Acyl-, 3-acyl- and 1,3-diacyl-3-furfuryl-1-phenylthioureas with platelet antiaggregating and other activities. Ranise, A., Bondavalli, F., Bruno, O., Schenone, S., Donnoli, D., Parrillo, C., Cenicola, M.L., Rossi, F. Farmaco (1991) [Pubmed]
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