A novel 5-((4-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)phenylamino)methyl)quinolin-8-ol (HTPSMQol) was synthesized by optimized reaction of 4-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)aniline with 5-chloromethyI-8-hydroxy_ quinoline hydrochloride (CMHQ). Also complexes of HTPSMQol were prepared by using various M (II) metal salts. All compounds were analyzed by spectroscopic techniques and screened against various strains of microorganisms. The results showed higher antimicrobial activity of HTPSMQol compared to its metal complexes and comparable with Ciprofloxacin.