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10.24.2 Pyrimido[1,2-a]indoles and Related Benzo-Fused Ring Systems

DOI: 10.1055/sos-SD-110-01955

Harris, P. A.Science of Synthesis Knowledge Updates, (2021385.

General Introduction

The synthesis and chemistry of pyrimido[1,2-a]indoles as a subclass will be reviewed in this section. Because the published chemistry around the core tricycle pyrimido[1,2-a]indole (1) is limited, the ring systems of indolo[1,2-a]quinazoline (2) and indolo[2,1-b]quinazoline (3), which are benzo-fused at the pyrimidine ring, are included in the scope for this chapter. To avoid confusion, because they are grouped together, the numbering system for chapter subheadings will follow that for the core pyrimido[1,2-a]indole (1) tricycle, as illustrated in Scheme 1. Ciclazindol (4), which contains the tricyclic core, was developed but never marketed in the mid-1970s, initially as an antidepressant, and later as an anorectic drug, primarily due to its norepinephrine reuptake inhibition.[‌1‌,‌2‌] Indolo[1,2-a]quinazolin-5-ones have also been studied as protein kinase CK2 and PARP-1 inhibitors.[‌3‌,‌4‌] A number of natural products contain the indolo[2,1-b]-quinazoline ring system, such as tryptanthrin (5), an alkaloid isolated from the dried roots of medicinal indigo plants, and its derivative candidine (6), also known as qingdainone.[‌5‌,‌6‌]

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