Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogs

Abstract

1,2-Dihydro-1-hydroxy-2-(organosulfonyl)areno[d] [1,2,3]diazaborines 2 (arene = benzene, naphthalene, thiophene, furan, pyrrole) were synthesized by reaction of (organosulfonyl)hydrazones of arene aldehydes or ketones with tribromoborane in the presence of ferric chloride. The activities of 2 against bacteria in vitro and in vivo (Escherichia coli) were determined and structure-activity relationships are discussed. Included in this study are 2,3-dihydro-1-hydroxy-2-(p-tolylsulfonyl)-1H-2,1-benzazaborole+ ++ (3) and 1-hydroxy-1,2,3,4-tetrahydro-2-(p-tolylsulfonyl)-2,1-benzazabor ine (4) as well as the carbacyclic benzodiazaborine analogue 4-hydroxy-3-(p-tolylsulfonyl)isoquinoline (7). The nature of the active species is briefly discussed.

The Drug Diazaborine Blocks Ribosome Biogenesis by Inhibiting the AAA-ATPase Drg1

“…Diazaborine is a heterocyclic boron-containing compound with strong antimicrobial activity (11). In Gram-negative bacteria the drug blocks fatty acid biosynthesis by inhibiting the enoyl-ACP reductase FabI (12,13).…”

Diazaborine Resistance in the Yeast Saccharomyces cerevisiae Reveals a Link between YAP1 and the Pleiotropic Drug Resistance Genes PDR1 andPDR3

“…Diazaborines are heterocyclic boron-containing compounds that exhibit strong antibacterial activity (15,16). These drugs cause inhibition of fatty acid and phospholipid biosyntheses in Gram-negative bacteria, like Escherichia coli or Salmonella typhimurium (17).…”

Abordagem racional no planejamento de novos tuberculostáticos: inibidores da InhA, enoil-ACP redutase do M. tuberculosis

“…O principal problema desta classe de compostos é o seu inerente potencial tóxi-co, o qual é provavelmente devido à porção amida ácida arenoborônica da molécula (Grassberger et al, 1984;Baldock et al, 1998).…”