This work has been carried out to investigate some reactions of 4,5,6,7-tetrahydrobenzo[b]thiophene derivatives 1a,b to give synthesis a series of novel heterocyclic products like N-ethoxymethino derivatives (2a, 2b), N-phenylaminomethino derivatives (3a, 3b), hydrazine derivatives (5a-d), pyrazole derivatives (7a-d, 10a-d, 11a, 11b) and N-methinonitrilo derivatives (9a-d). The antitumor evaluation of the newly synthesized compounds against the three human tumor cells lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of these compounds exhibit much higher inhibitory effects towards the three tumor cell lines than the positive control doxorubicin. Moreover, they were tested against normal cells namely diploid normal human fibroblast (WI-38), Normal prostate epithelial cells (PrEC) and normal human mucosal epithelial cells (NCM 460). The anti-leishmanial evaluations of the obtained compounds were also performed. Compounds 7d and 10b were the most active towards tumor cell lines while compounds 3a, 3b, 9b and 9d were the most active compounds as anti-leishmanial. Docking of these most active compounds was demonstrated