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10.24.4 Pyrazino[1,2-a]indoles and Related Benzo-Fused Ring Systems

DOI: 10.1055/sos-SD-110-02056

Harris, P. A.Science of Synthesis Knowledge Updates, (20213145.

General Introduction

The synthesis and chemistry of pyrazino[1,2-a]indoles as a subclass will be reviewed in this section. Because the published chemistry around the core tricycle pyrazino[1,2-a]indole (1) is limited, the synthesis of two related ring systems, the more common benzo-fused indolo[1,2-a]quinoxaline (2) and less reported pyrido[2,1:3,4]pyrazino[1,2-a]indol-5-ium salts 3, are included in this chapter. To avoid confusion, because they are grouped together, the numbering system for chapter subheadings will follow that for the core pyrazino[1,2-a]indole (1) tricycle, as illustrated in Scheme 1. Both pyrazino[1,2-a]indole- and indolo[1,2-a]quinoxaline-containing ring systems have attracted attention for their biological activities. Pyrazino[1,2-a]indol-1-ones such as 4 have been studied for their ability to inhibit generation of reactive oxygen species, antioxidant activity, and anticancer activity against a panel of cancer cell lines.[‌1‌] Indolo[1,2-a]quinoxalines such as 5 show inhibition of vascular endothelial growth factor receptor 3 kinase, which plays a role in tumor metastasis, whilst 5,6-dihydroindolo[1,2-a]quinoxaline 6 shows antifungal activities.[‌2‌,‌3‌]

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