Homologated aza analogs of arabinose as antimycobacterial agents

A series of hydrolytically-stable aza analogs of arabinofuranose was prepared and evaluated against Mycobacterium tuberculosis and M. avium. The compounds were designed to mimic the putative arabinose donor involved in biogenesis of the essential cell wall polysaccharide, arabinogalactan. Though most compounds displayed little activity in cell culture, one compound showed significant activity in infected macrophage models. A series of hydrolytically-stable aza analogs of arabinofuranose was prepared and evaluated against Mycobacterium tuberculosis and M. avium in broth assays and in macrophages. One of the compounds, an analog of the putative arabinose phospholipid donor in arabinogalactan biosynthesis, showed significant activity in the macrophage model.