Synthesis of Novel Drug‐Like Small Molecules Based on Quinoxaline Containing Amino Substitution at C‐2

Abstract

A series of novel "drug-like" small molecules based on quinoxaline containing amino substitution at C-2 were synthesized. All these molecules were prepared either via the reaction of 2-phenyl-3-(piperazin-1-yl) quinoxaline with acyl bromides or benzyl bromides or various carboxylic acids or via the reaction of 2-chloro-3-phenylquinoxaline with various amines. The structures of these novel compounds were confirmed by spectral analysis. The strategy used is simple and efficient and afforded good yields of quinoxaline derivatives.

Synthesis of quinoxaline derivatives from terminal alkynes and o-phenylenediamines by using copper alumina catalyst

“…With the optimized reaction conditions mentioned above, a variety of substrates were studied to check limitation of this reaction using several derivatives of substituted o-phenylenediamines and terminal alkynes (Table 4 # [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. The terminal aryl alkynes bearing an electrondeficient group such as -F with o-phenylenediamine afforded an excellent yield (Table 4 # 1).…”

“…Quinoxaline derivatives are one of the important biologically active heterocyclic compounds within which benzene and pyrazine rings are clubbed together. 1,2 It has evoked considerable attention as they exhibit pharmacological activity; antibacterial, antifungal, antiviral, antimicrobial, antimalarial, anti-inflammatory, antidepressant and anticancer activity. [3][4][5][6] Quinoxaline derivatives are also used in agriculture 7 (fungicides, herbicides, and insecticides), dye industries and as corrosion inhibitors.…”

Construction of a novel quinoxaline as a new class of Nrf2 activator

“…Quinoxaline, fused ring of benzene and pyrazine, is one of the important class of heterocyclic compound having diverse biological activities (Burguete et al 2011;Moody et al 2015;Nakhi et al 2012;Patidar et al 2011;Pereira et al 2015;Raghavendra Rao et al 2015;Wu et al 2012) and present as integral part of diverse bioactive compounds and pharmaceuticals (Burguete et al 2007;Hazeldine et al 2002;Jaso et al 2005;Rong et al 2007;Smits et al 2008). Hydrazines are nitrogennitrogen bond containing compounds which exhibit remarkable biological activities (Le Goff and Ouazzani 2014;Kajal et al 2014;Narang, Narasimhan, and Sharma 2012;Rollas and Küçükgüzel 2007).…”