Quinoxaline derivatives: a patent review (2006 – present)

Abstract

We centred our discussion in the various drug patent applications of the quinoxaline and its derivatives. The applications are based firstly in the specific enzyme target with very low development in the disease treatment. Only for cancer and antimicrobial agents they were specifically determined but little is mentioned in order to insight in the last development activities.

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

“…Finally, we also investigated the formation of C À C bonds at two other pharmaceutically relevant heterocyclic substrates, such as quinazoline and quinoxaline. [8] As shown in Figure 4, the results obtained were again satisfactory, and these reactions allowed the preparation of compounds 16-22. 2-(3-Indolyl)-quinoxaline 21 had been previously prepared in 47% overall yield via a multistep sequence based on the construction of the quinoxaline ring from an indole ketoaldehyde precursor, [14d] or in two steps and 58% overall yield from 3-acetylindole.…”

“…[1,2] Cross-coupling reactions able to generate carbon-carbon (C À C) and carbon-nitrogen (C À N) bonds on nitrogen heterocyclic substrates are of great importance in the synthesis of a large variety of bioactive compounds. Some examples include indolylquinolines, which play an important structural role in several biological processes and have been shown to possess antileishmanial and antibacterial activities, [3] derivatives of the quinazoline and acridine nuclei with anticancer, [4,5] antimalarial [6] and a variety of other pharmacological activities, [7] and derivatives of quinoxaline, [8] purine, [9] pyridine [10] and benzimidazole, [11] also with a considerable biomedical interest. Some representative examples are shown in Figure 1.…”

Fe3O4@APTES@isatin-SO3H as heterogeneous and efficient catalyst for the synthesis of quinoxaline derivatives

“…Recently, the chemists have greatly focused on developing the eco-friendly catalysts and methods in the synthetic organic material and industrial fields [1,2].Over the last few decades, a growing research interest has been directed towards the preparation and application of highly efficient and recyclable catalysts in the modern synthetic processes [3][4][5][6].Magnetic Fe 3 O 4 nanoparticles have emerged as privileged support for immobilization of various functional groups such as phosphorous, nitrogen and organic moieties owing to the presence of high density hydroxyl groups on their surface, high surface area, high stability, facile magnetic separation, environmental benignity and high loading capacity [7][8][9][10][11][12][13][14][15][16][17][18]. Among the heterocyclic compounds, quinoxaline and derivatives are the most important compounds due to their biological and pharmacological properties which perform antifungal [19], insecticide [20], antibacterial [21], anticancer, antimalarial, anti-HIV [22] and antibiotics [23] activities. In addition, quinoxaline derivatives are used in industry, in dyes, fluorescent dyes, materials having electroluminescence properties and in the synthesis of organic semiconductors [24].…”

Synthesis and cytotoxic evaluation of novel quinazolinone derivatives as potential anticancer agents

“…Quinoxaline as like as Quinazoline is N-containing heterocyclic compound with especial therapeutic activities of anti-inflammatory( 18 ), antifungal( 19 ), antibacterial( 20 ), antileishmanial( 21 ), anti-herpetic( 22 ) anti-HIV( 23 ) and anticancer( 24 ). Quinoxaline derivatives have anticancer activity with various mechanisms including topoisomerase inhibition( 25 ), DNA cleaving( 26 ), arresting the G1 phase and kinase inhibition( 27 ).…”