Synthesis and Antimicrobial Activity of Novel Quinoxaline Derivatives

Abstract

In this study, certain 3‐substituted styrylquinoxalin‐2(1H)‐ones (2a‐d) and their 2‐chloro (3a‐d) and 2‐piperazinyl derivatives (4a‐g) were synthesized from 3‐methylquinoxalin‐2(1H)‐one (1). In addition, a series of 1‐alkyl‐3‐substituted styrylquinoxalin‐2(1H)‐ones (5a‐d) was also prepared. Moreover, 3‐(N2‐arylidenehydrazinocarbonyl)quinoxalin‐2(1H)‐ones (8a‐c) as well as their cyclized oxadiazolinyl derivatives (9a‐c) were prepared from 3‐hydrazinocarbonylquinoxalin‐2(1H)‐one (7). Furthermore, 3‐(5‐substituted thio‐1,3,4‐oxadiazol‐2‐yl)quinoxalin‐2(1H)‐ones (11a‐c) and (12a‐c) were obtained from the intermediate compound (10) ‐ previously obtained via cyclization of (7) with CS2. Likewise, 3‐(5‐oxo‐4,5‐dihydro‐(1,3,4‐oxadiazol‐2‐yl)quinoxalin‐2(1H)‐one (13), 3‐[5‐(4‐nitrophenyl)‐1,3,4‐oxadiazol‐2‐yl]‐quinoxalin‐2(1H)‐one (14) and its 2‐chloro derivative (15) were prepared from 3‐hydrazinocarbonylquinoxalin‐2(1H)‐one (7). Some of these derivatives were evaluated for antimicrobial activity in vitro and some of the tested compounds showed antibacterial or antifungal activity.

Structure Parameter Correlation of some Quinoxaline Derivatives through IR and ¹³C NMR Spectra

“…The important biological activities of quinoxalines are antibacterial [2,3], antiviral [4], anti-inflammatory [4], askinase inhibitors [4], anticancer [4], antimycobacterial [5,6], antifungal [7], anthelmintic [4,7], antidepressants [8] and antitumour [9,10]. Many kinds of synthetic methods including solvent-free and catalysts were reported in the literature for synthesis of quinoxalines by the condensation of 1,2-diamines and 1,2-dicarbonyl compounds [1,2,11].…”

Fe3O4@SiO2/Schiff base complex of metal ions as an efficient and recyclable nanocatalyst for the green synthesis of quinoxaline derivatives

“…The synthesis of quinoxaline derivatives has been of considerable interest as they possess various biological activities, such as antibacterial (1), anthelmintic (2), antitumor (3), antifungal (1), antidepressant (4), and kinase inhibition agents (5). In addition, quinoxalines have been used for the preparation of various dyes (6) and key intermediates in the synthesis of organic semiconductors (7), dehydro annulenes (8), chemically controllable switches (9), and used in the agricultural field as fungicides, herbicides, insecticides (2).…”

Oxonium heterocyclic quinone in the synthesis of some cyanine dyes and their antimicrobial activity

“…Cyanine dyes are colorant compounds used in staining of internal limiting membrane (ILM) [18] and used as fluorescent dyes in DNA detection [19][20][21][22][23]. Quinone derivatives are widely used as fungicides [24,25], and antibacterial agent [25][26][27][28][29]. This paper reports the synthesis and characterization of a series of new monomethine, trimethine and styrylmethine cyanine dyes, and also their structure-property relationship of these dyes from their visible absorption spectra.…”