In pursuit of novel antibacterial fluoroquinolones
LE3 .A278 2006
Bachelor of Science
Fluoroquinolones are a class of synthetic antibacterial agents used to fight against the ever growing and evolving amount of bacterial infections currently affecting people worldwide. Among other substituents, these compounds bear a carboxylate group at position 3 and an N-heterocyclic ring at position 7 of the quinolone ring. As part of a larger research initiative in our lab, fluoroquinolones were designed where a phosphonate group replaced a carboxylate group and new heterocyclic rings (4-aminopiperazinyl and 4-amino-3,5-dimethylpiperidinyl) were introduced. For the present investigation, efforts were made to synthesize these heterocyclic rings. 4-Tert-butoxycarbonylamino-1-benzylpiperazine and 4- nitro-3,5-dimethylpyridine were synthesized as precursors to 4-tertbutoxycarbonylaminopiperazine and 4-amino-3,5-dimethylpiperidine respectively. The final reaction steps could not be completed owing to time constraints. After successful synthesis of these heterocyclic ring systems, synthesis of fluoroquinolone-3-phosphonates will be undertaken. Eventually the two will be attached to yield the target compounds. It is hoped that the final products will not only show enhanced potency to known fluoroquinolones, but will also be effective against resistant strains of bacteria.
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