Microwave Assisted Synthesis of New Imines of 7-Aminocephalosporinic Acid as Potent Antibacterial Agents

Title:Microwave Assisted Synthesis of New Imines of 7-Aminocephalosporinic Acid as Potent Antibacterial Agents

Volume: 1 Issue: 2

Author(s): A.B. Thomas, S.P. Moharil, R.K. Nanda, S.G. Dhokrat, L.K. Kothapalli and M.V. Nanwatkar

Affiliation:

Keywords: Alpha-halo ketones, fragment-based design, imines of 7-ACA, microwave irradiation, N-heterocycles.

Abstract: A series of new imines of 7-Aminocephalosporinic acid (7-ACA) were synthesized by fragment-based design using smaller and functionally simpler adducts like alpha-halo ketones, N-heterocycles and 7-ACA with good success to generate chemical compounds with drug-like properties effective against Staphylococcus aureus and Pseudomonas aeruginosa which are resistant to several antibiotics and are responsible for a large number of community acquired infections. In the first step, N-aryl substituted ketones were synthesized in excellent yields (90-96%) in a single step reaction (Scheme 1) with various heterocyclic rings in the presence of solvents like ethanol/DMF using microwave irradiation method in shorter reaction times (10-12 mins) with higher yields (90-95%). Further, the microwave assisted synthesis of imines of 7-ACA from corresponding ketones (Scheme 2) with ethanol as the solvent in the presence of molecular sieves resulted in target compounds with improved yield (90-94%) in short reaction times (12-14 min). The use of microwave assisted synthetic route and greener and environmentally benign solvents resulted in improvement of rates (energy savings), yields and selectivity (reduced wastes) of the target compounds.

Cite this article as:

Thomas A.B., Moharil S.P., Nanda R.K., Dhokrat S.G., Kothapalli L.K. and Nanwatkar M.V., Microwave Assisted Synthesis of New Imines of 7-Aminocephalosporinic Acid as Potent Antibacterial Agents, Current Microwave Chemistry 2014; 1 (2) . https://dx.doi.org/10.2174/2213335601666140806010137