A series of tetrahydrobenzo[b]thieno[2,3-d]pyrimidines, thieno[3,2-e]imidazo[1,2-c]pyrimidines and thieno[2,3-d][1,3]thiazines was synthesized as antitumor, antiviral agents. Compounds (2) under bar, (3) under bar and <(17)under bar> possessed moderate Anti-HIN-1 potency with EC(50) values ranging from 1.83 x 10(-5) to 3.42 x 10(-5) molar concentrations. All of the tested compounds showed cytotoxic effects (log GI(50) less than or equal to -4.0) against the growth of a variety of human tumor cell lines, including those derived from solid tumors. Compounds (3) under bar and (7) under bar showed strong potency while compounds <(11)under bar> and <(16)under bar> exhibited moderate activity. The detailed synthesis, spectroscopic and biological data are reported.