Heterocycle-Fused Acridines

Abstract

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Challenges and Rewards of Research in Marine Natural Products Chemistry in Brazil

“…The structure of sebastianine A was recently confirmed by total synthesis . Pyridoacridine alkaloids have been isolated mainly from ascidians, but also from marine sponges, from a sea anemone, and from a marine mollusk belonging to the order Prosobranchia. , Salomon et al proposed that the occurrence of pyridoacridine-related alkaloids in animals belonging to phylogenetically distant taxa seems to be an indication that “where a bioactive metabolite can be produced in an energetically favorable manner from simple precursors, the same or similar biosynthetic pathways might have evolved in different phyla”, rather than produced by associated microorganisms. A similar statement has been recently proposed by Skyler and Heathcock, who suggested a “pyridoacridine family tree”, on the basis of which these authors predicted the existence and future isolation of new, biogenetically related compounds.…”

1H and13C chemical shifts of some tetracyclic and pentacyclic acridinone derivatives

“…Therefore, the synthesis of new polycyclic heteroaromatic acridine compounds has increased rapidly in the last few years.1,2 In this respect, we have recently described the preparation and NMR spectral data for, e.g., pyrazolo 7,8 In this paper, we report the complete 1H and 13C NMR chemical shift assignments obtained from one-and two-dimensional NMR techniques for the following new classes of fused acridinones : thiazolo [5,4-a]acridin-11(6H)-one (1b-7b), thiazolo [4,5-a]acridin-11(6H)-one (8b-9b), imidazo [5,4-a]acridin-11(6H)-one (10b-15b), triazolo [1,2,4] thiazolo [5,4-a]acridin-12(7H)-one (16c-19c) and triazolo [1,2,4] imidazo [5,4-a]acridin-12(7H)-one (20c) (Fig. 1).…”

Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo[3,4-j]acridine

“…6 They also find applications in the search for new biologically active compounds and diagnostic methods. 7 Among the various fluorescent heterocyclic compounds, acridines are one of the oldest classes of heterocyclic compounds extensively used as dyes and pigments since the 19th century 8,9 and have been commercialised for more than a century. In particular, some of them have been found to be efficient fluorescent chemosensors for the recognition of transition metal ions, such as Hg 2+ , 10 and emitters for luminescence studies.…”