A series of some novel Ethyl 2-((1-hydroxynaphthalen-2-yl)methyleneamino)-5,6-dihydro-4H-cyclopenta[b]thiopehene-3-carboxylate, Ethyl 2-((1-hydroxynaphthalen-2-yl)methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate, Ethyl 2-((1-hydroxynaphtalen-2-yl)methyleneamino)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate and their Cr(III) and Zn(II) complexes have been synthesized. All of these substances have been examined for antibacterial activity against pathogenic strains Listeria monocytogenes 4b (ATCC-19115), Staphylococcus aureus (ATCC25923), Proteus OX2 Wrah (ETS.40-A-4), Escherichia coli (ATCC-1280), Salmonella typhi H (NCTC-901.8394), Pseudomonas putida sp., Brucella abortus (A.99, UK-1995) RSKK-03026. Sh. boydii type 11 (Pasteur51.6), Sh. boydii type 16 (cHe 67.11), Sh. boydii type 6 (RSKK-96043), and antifungal activity against Candida albicans (Y-1200-NIH, Tokyo). Some of the compounds exhibited activity comparable to ampicillin ofloxacin, nystatin, kanamycin, sulphamethoxazol, amoxycillin, and chloroamphenicol. Most of the studied compounds were found effective against bacteria studied and yeast.