Structure-activity relationship of diphenylthiourea antivirals

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Abstract
The dependence between chemical structure and antiviral activity of N,N''-diphenylthioureas is studied by synthesis and testing of model compounds and use of conformational data. The analysis revealed a number of structural features as essential for the antiviral effect: the presence of an intact -NHC(.dbd.S)NH- grouping; the presence of a substituent of the XH type (X = 0, NH) in the aromatic ring; the distance between these substituents and the S atom in the 6.68-6.75 .ANG. range for the active compounds; a trans conformation of the -C(.dbd.S)NH-group bound to the substituted phenyl ring. The directed synthesis of compounds satisfying the above requirements yielded the derivative N-phenyl-N''-(m-aminophenyl)thiourea exhibiting a very high antipicornavirus activity in vitro and several other active analogs (4 of 7 synthesized). The possible mechanism of interaction between the active diphenylthiourea derivatives and the viral target is discussed.