A series of N'-substituted 1,4-benzodiazepine-1-carbothioamides 2a-j were prepared by reacting the precursor 1,4-benzodiazepine 11 with the corresponding N-substituted isothiocyanates 2a-i or with sodium thiocyanate-trifluoroacetic acid (2j). Despite the structural ressemblance of these molecules with the potent TIBO-type anti-HIV compound R82150, 2a-j displayed no anti-HIV activity in vitro.