A Survey of Synthetic Routes and Antitumor Activities for Benzo[g]quinoxaline-5,10-diones

Abstract

Anthracycline antibiotics play an important role in cancer chemotherapy. The need to improve their therapeutic index has stimulated an ongoing search for anthracycline analogs with enhanced properties. This review aims to summarize the common synthetic approaches to benzo[g]quinoxaline-5,10-diones and their uses in heterocyclic chemistry. Because of the valuable biological activities of the 1,4-diazaanthraquinone compounds, a summary of the most promising heterocyclic quinones is provided together with their antitumor properties.

Chemistry, Synthesis, and Structure Activity Relationship of Anticancer Quinoxalines

“…The first and the second ionization states were calculated by photon electron spectroscopy, and they were 8.99 and 10.72 eV, respectively [47][48][49][50]. The past twenty years have witnessed huge progress in the synthesis of quinoxaline derivatives [51][52][53][54][55]. These synthetic processes focused on function groups and their tolerance, product variation, selective catalysis, and substrates [56][57][58].…”

The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review

“…The hydroxyl-1,4 naphthoquinones such as juglone 2, lawsone 3, plumbagin 4, and lapachol 5 are natural NQs isolated from plants extensively used in traditional Indian medicine [15][16][17][18]. In the past decades, the substitution of diverse groups and modifications in the NQs ring have provided many derivatives with enhanced biological activity [19][20][21][22][23][24][25][26][27][28][29][30][31][32]. In this respect, lawsone derivatives, 3-(aminomethyl)-2-hydroxy-1,4-naphthoquinones 6, or amino naphthoquinone Mannich bases have been synthesized and evaluated as anticancer, antimalarial, antiviral, antifungal, and antibacterial molecules [19,20]; amino 7, and thioether 8 NQs (Figure 1), as well as the NQs with aromatic amines in carbon two or three, may tune their antifungal and antibacterial activity and anticancer activity, being the case for 2-acetyl-3-aminophenyl-1,4-naphthoquinones 9, which has been evaluated for in vitro antiproliferative activity against several types of human cancer cells with very promising results [21].…”

“…For instance, several compounds containing NQ and triazole nuclei in their structure have shown a more potent antibacterial effect than the active groups alone. Therefore, since both groups inhibit bacteria independently, a synergic effect must occur to enhance biological activity [27][28][29][30][31].…”

Synthesis of novel antibacterial and antifungal quinoxaline derivatives

“…Quinoxaline derivatives, a class of N-containing heterocyclic compounds, which is an important chemical intermediate, have played an important role in the design and synthesis of new heterocyclic compounds, 13 and are of great signicance for drug discovery. 14 Quinoxaline derivatives exhibit broadspectrum bioactivities, such as antibacterial, 15,16 antiviral, 17,18 antitumor, [19][20][21] anti-tuberculous, 22 anticancer, 23,24 and so on. 25,26 Therefore, quinoxaline moieties widely exist in pesticides and medicines, and some commercialized pesticides used in agricultural production, including quintiofos, quizalofop-p-ethyl, chloramphenicol, olaquindox, and so forth (Fig.…”