Synthesis of Triazoloquinoxalines as Antitubercular Agents

Abstract

1,2,4-Triazoles and quinoxalines were found to display various pharmacological activities. Hence a series of 1-aryl-4-methyl-1,2,4-triazolo[4,3-a]quinoxalines were synthesized. Due to various advantages of organic reactions under solvent-free conditions these compounds were developed using iodobenzene diacetate under solvent-free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, 1 H NMR, 13C NMR and HRMS. All the synthesized compounds were investigated for their antitubercular activity and 5g was found to the most active compound.

[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines

“…The [1,2,4]triazolo[4,3- a ]quinoxaline scaffold ( Figure 1 ) is made up of fused triazole and quinoxaline, which are privileged fragments possessing diverse biological activities. Researchers have demonstrated the high potential of this tri-heterocycle for a wide spectrum of pharmacological properties [ 22 ], such as anticancer [ 23 , 24 ], antibacterial [ 25 , 26 , 27 , 28 , 29 ], antiviral [ 30 , 31 ], antifungal [ 32 , 33 , 34 ], antiparasitic [ 35 ], cardiac modulator [ 36 , 37 , 38 ], anti-neurodegenerative [ 39 ], or immunomodulator agents [ 40 ]. Among the recent [1,2,4]triazolo[4,3- a ]quinoxalines displaying anticancer activities, Ezzat et al designed and synthetized potent A2B adenosine receptor antagonists with hydrophobic aryl tails linked in the C4 position through a hydrophilic group, which afford low-micromolar-range cytotoxic activities on the human triple-negative breast adenocarcinoma MDA-MB-231 cell line [ 41 ].…”

“…More reactive species, such as chloride acids, also make it possible to constitute the triazole conjugated with quinoxaline (Route C, Scheme 1) [69]. Alternatively, aldehydes are also described as potent reagents to build [1,2,4]triazolo [4,3a]quinoxalines with a variety of alkyl or aryl moieties (Route D, Scheme 1) [29,31,34,70]. Treatments of the hydrazinoquinoxaline intermediates with reagents like phosgene [71,72], thiophosgene [73], or carbone disulfide in pyridine [42,67] provide 1-oxo and 1-thio analogues, respectively (Route E, Scheme 1).…”