3-Substituted 2-formylquinoxaline 1,4-dioxides

Abstract

The methylnitrone of 3-methyl-1,4-dioxidoquinoxaline-2-carboxaldehyde (1) has been exceptional antibacterial activity in vivo. Derivatives of 3-hydroxymethyl-1,4-dioxidoquinoxaline-2-carboxaldehyde and 3-acetoxymethyl-1,4-dioxidoquinoxaline-2-carboxaldehyde were prepared. Several of these compounds were found to be antibacterial agents of the same order of activity as I.

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

“…These authors proved that a metabolic bioactivation in the sheep of 2,3-dimethylquinoxaline 1,4-dioxides take place to afford the more active 2-hydroxymethyl-3-methylquinoxaline 1,4-dioxide. On the other hand subsequent studies of Edwards et al reported that 3-hydroxymethyl-1,4-dioxidoquinoxaline-2-carboxaldehyde and 3-acetoxymethyl-1,4-dioxidoquinoxaline-2-carboxaldehyde derivatives were in vivo active at the same order of activity of methylnitrone derivative [85]. The activity of nitrone derivatives was also studied by Bambury et al [86][87].…”

1,2,3,4-Tetrahydrophenazine 5,10-dioxide

“…For the synthetic preparation, see: Haddadin & Issidorides (1965); Issidorides & Haddadin (1966). For background to quinoxaline di-N-oxide compounds, see: Edwards et al (1975) and for their biological activity, see: Urquiola et al (2008). For a related structure, see: Wang et al (2010).…”

“…Quinoxaline di-N-oxide compounds are widely used in sterilization and growth-promoting of animals, pharmacological properties usable as intermediates for producing plant protection agents (Edwards et al,1975). There has been a growing interest in the syntheses of quinoxaline di-N-oxide compounds that have both biological and commercial importance (Urquiola et al, 2008).…”

Quinoxaline Mono‐ and Di‐ N ‐Oxides

“…97 The high in vivo activity of 2,3-dimethyl- In addition to their use as feed additive^,^^"^ quinoxaline 1,4-dioXides have been patented for the treatment of diseases in aquatic animals'03 and as fungicides and herbicide^.^,^'^ There is also a report of the prophylactic effect of 6-chloro-2,3-dimethylquinoxaline 1,4-dioxide and 2,3-dimethylquinoxaline 1,4-dioxide on radiation injuries in mice.lo5 Tables TABLE 1. It has been shown that its in vitro activity is enhanced 10 to 100-fold under anaerobic conditions.…”