Synthesis and Antimicrobial Studies of 6-Aryl and 6-Anilino Benzo[a]phenoxazinones

Abstract

Palladium catalyzed Suzuki-Miyaura (SM) and Buchwald – Hartwig (BH) cross-coupling reactions of some phenoxazines are reported. The precursor 9,11-diamino-6-chloro-7-oxa-8,10,12-triaza-benzo [a] anthracen-5-one was prepared by anhydrous base mediated reaction of 2,5,6-triamino-pyrimidin-4-ol and 2,3-dichloro-1,4-naphthoquinone in methanol. The molecular structures of the synthesized compounds agreed with UV/visible, FT-IR, 1H-NMR, MS and elemental analysis data. Using Ciprofloxacin and Ketoconazole as reference drugs, the compounds were screened against six (6) micro-organisms, viz: Listeria ivanovii, Staphylococcus aureus, Klebsiellapneumoniae, Escherichia coli, Candida albicans and Aspergillusnigerand were found to show significant activity against L.ivanovii and E. coli bacteria.

Pharmacological Activities of Aminophenoxazinones

“…Recent studies [ 102 ] evaluated the antimicrobial activity of 8 derivatives ( 8 – 15 ) of phenoxazines against the bacteria Listeria ivanovii , E. coli , S. aureus and Klebsiellapneumoniae spp., and against the fungi C. albicans and Aspergillusniger spp. For the synthesis of the compounds, in a first stage, 5 was synthesized, then, the rest of compounds were obtained by arylation (compounds 9 – 12 ) or amination (compounds 13 – 15 ) reactions of 8 ( Figure 11 ).…”