2-(Benzo[d]thiazol-2-yl) phenyl-4-nitrophenyl alkyl/aryl substituted phosphoramidates: Synthesis,characterization and antimicrobial activity evaluation |
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Authors: | S Munichandra Reddy D Subba Rao K Madhu Ch Subramanyam P Gnana Kumari |
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Institution: | 1. Department of Chemistry, Sri Padmavathi Degree and PG College, Tirupati, Andhra Pradesh, India;2. Chemical Research &3. Development, API Division, Micro Labs Ltd., Jigani-Bommasandra Link Road, Bangalore, Karnataka, India;4. Deparment of Chemistry, Bapatla Engineering College, Bapatla, Andhra Pradesh, India |
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Abstract: | A series of new 2-(benzod]thiazol-2-yl) phenyl-4-nitrophenyl alkyl/aryl substituted phosphoramidate derivatives (7a-j) of biological interest are synthesized in two steps via an in situ process without the isolation of the intermediate. 2-(Benzod]thiazol-2-yl) phenol (3) was treated with 4-nitrophenyl phosphorodichloridate(4) to obtain the monochloro intermediate, 2-(benzod]thiazol-2-yl)phenyl (4-nitrophenyl) phosphorochloridate(5). It was subsequently reacted with various amines, 6(a-j) to afford the desired title products. IR, NMR (1H, 13C and 31P), mass spectral and elemental analysis are used to characterize the structures of the newly synthesized compounds. The antibacterial and antifungal activities are determined by the growth of inhibition of bacteria and fungi of the title compounds at two concentrations, 50 and 100 µg/mL, and minimum inhibitory concentrations to the active compounds. The compounds 7e, 7f and 7j exhibited promising inhibition activity against bacterial strains and 7c, 7e and 7i against A. niger and C. albicans and MIC values are in the range of 10.0–15.0 µg/mL. |
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Keywords: | 2-(Benzo[d]thiazol-2-yl) phenol Phosphoramidates antimicrobial activity minimum inhibitory concentration |
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