Synthesis of new 2(1H)-quinoxalinone derivatives for antimicrobial and antiinflammatory evaluation

Abstract

New 2(1H)-quinoxalinones and their hexahydro derivatives were prepared for investigating their antimicrobial and antiinflammatory activities. The study showed that thiosemicarbazide 6a derived from the hexahydro-2(1H)-quinoxalinone series has nearly the same antibacterial activity as the reference drug ciprofloxacin. Moreover, the 2(1H)-quinoxalinones bearing N-phenyltriazole (9a) or 4-chlorophenyl-2,3-dihydrothiazole (13b) moieties were the most active ones after 4 h with use of the rat hind paw edema method, whereas their antiinflammatory and ulcerogenic activities were comparable with the selective COX-2 inhibitor celecoxib.

A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

“…For example, the quinoxaline ring is a constituent of various bioactive compounds that possess antibiotic, anti-inflammatory, antimicrobial [5], antidiabetic [6], and antiviral activity against retroviruses including HIV [7]. In addition, quinoxaline derivatives are also associated with a wide spectrum of biological effects including anticancer [8], antifungal, and antidepressant activities [9–10].…”

Radiation-induced reduction of quinoxalin-2-one derivatives in aqueous solutions

“…Quinoxaline-2-one derivatives are particularly interesting since some of them showed a variety of pharmacological properties, such as antimicrobial (Ajani et al, 2010;El-Sabbagh et al, 2009;Sanna et al, 1998;Sanna et al, 1999), antiviral (Xu et al, 2009), antifungal (Carta et al, 2002;Ingale et al, 2007;Sanna et al, 1999), anxiolytic (Ulrich et al, 1998), analgesic (Ingale et al, 2007), antiinflammatory (El-Sabbagh et al, 2009), antithrombotic (Ries et al, 2003;Willardsen et al, 2004), and antitumor (Hirai et al, 2011;Koth et al, 2007;Lawrence et al, 2001;Meyer et al, 2006) activities. Based on the computer modeling and "in vitro" studies, quinoxalin-2-ones have been proposed as potential drugs in treatments of various diseases (Carta et al, 2006).…”

6-Methyl-1,4-bis[(pyridin-2-yl)methyl]quinoxaline-2,3(1H,4H)-dione

“…Quinoxalines and their derivatives are a varied class of nitrogen-containing heterocyclic compounds, which display various pharmacological and biological activities, such as anticancer (Carta et al, 2006), antimalarial (Guillon et al, 2004), antiviral (Fonseca et al, 2004), antibacterial (El-Sabbagh et al, 2009), antimicrobial (Singh et al, 2010), antiinflammatory (Wagle et al, 2008) and antiprotozoal (Hui et al, 2006). In this work, we report the synthesis of a new quinoxaline derivative by the reaction of 2-picolyl chloride with 6-methyl-1,4-dihydroquinoxaline-2,3-dione in dimethylformamide in the presence of potassium carbonate and a catalytic quantity of tetra-n-butylammonium bromide.…”