An Overview on the Synthesis of Fused Pyridocoumarins with Biological Interest

Abstract

Pyridocoumarins are a class of synthetic and naturally occurring organic compounds with interesting biological activities. This review focuses on the synthetic strategies for the synthesis of pyridocoumarins and presents the biological properties of those compounds. The synthesis involves the formation of the pyridine ring, at first, from a coumarin derivative, such as aminocoumarins, hydroxycoumarins, or other coumarins. The formation of a pyranone moiety follows from an existing pyridine or piperidine or phenol derivative. For the above syntheses, [4 + 2] cycloaddition reactions, multi-component reactions (MCR), as well as metal-catalyzed reactions, are useful. Pyridocoumarins present anti-cancer, anti-HIV, antimalarial, analgesic, antidiabetic, antibacterial, antifungal, anti-inflammatory, and antioxidant activities.

p-Toluenesulfonic acid-promoted organic transformations for the generation of molecular complexity

“…64 Aryl glyoxals bearing electronrich and electron-poor substituents showed uniform reactivity, and the corresponding aryloyl group-containing dicoumarols were obtained in good yields. Khan and co-workers have explored the route to access biologically important 65 coumarin fused pyridine derivatives in acetonitrile under reflux conditions. 66 In their approach, a variety of phenylacetaldehyde derivatives were reacted with 3-aminocoumarins containing 7-MeO, 8-EtO, 8-MeO, 6-Br, 6-Cl, 6,8-dichloro substituents in the presence of 10 mol% p-TSA, affording the desired pyrido(2,3-c)coumarin derivatives after simple workup procedures with satisfactory yields (Scheme 44).…”

Bis(2-cyanoacetamide) in Heterocyclic Synthesis: Synthesis of Some Bis[2-oxopyridine, 2-iminochromene, Chromeno[3,4-c]pyridine, Benzochromeno[3,4-c]pyridine] Derivatives

“…Functionalized chromenes are widely used to synthesize promising compounds in medicinal chemistry [28][29][30][31][32][33][34][35] . Wide-ranging pharmacological activity, such as antibacterial 36 , anti-inflammatory 37 , antimicrobial 38 , anti-proliferative 39 , hypotensive 40 , and antirheumatic 41 properties, have been reported for derivatives of chromenopyridine. Many natural and pharmaceutical compounds contain fused chromenes like chromenopyridines.…”

Deaminative ring contraction for the synthesis of polycyclic heteroaromatics: a concise total synthesis of toddaquinoline

“…Polycyclic aromatic natural products exhibit a host of exciting biological properties, 1,2 and their highly varied arene substitution patterns have motivated creative strategies 3 for their assembly. Dehydrojuncusol 1 , 4 litebamine 2 , 5 toddaquinoline 3 , 6 and santiagonamine 4 , 7 serve to emphasize the diverse substitution patterns displayed by biologically active secondary plant metabolites that share the ‘phenanthrene skeleton’ (Fig.…”