Modified Pyridine-Substituted Coumarins: A New Class of Antimicrobial and Antitubercular Agents

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

“…The outcome of these assays revealed noteworthy antimicrobial efficacy of the synthesized compounds against the tested strains. 87 During investigations into the synthesis and chemical properties of spiroheterocycles, Moncef Msaddek and coworkers in 2014 revealed that when they subjected aurone 1 derivatives to a reaction with 2-diazopropane 149, it led to the formation of spirocyclopropane 150 compounds. While the anticipated outcome primarily comprised the formation of cycloadducts, there was an unexpected result in certain instances: the generation of oxadiazole 151 compounds.…”

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

“…As the oxidative state of flavones, flavonols can be produced from flavones by the oxidation with 3,3-dimethyldioxirane (DMDO) [174] or Algar-Flynn-Oyamada reaction in the presence of base and hydrogen peroxide [175,176], which may generate by-product of aurone due to the different attacking position of epoxide [177]. Selective synthesis of Scheme 17 Total-synthetic strategies of flavonoids by cyclization of 2'-hydroxychalcones aurone could be achieved through oxidative cyclization of 2'-hydroxychalcones mediated by Hg(OAc) 2 in a good yield [178,179]. Aurones can also be converted to flavonols by bromination, elimination and rearrangement, which was known as Auwers synthesis [180].…”

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

“…Compounds with a (4-benzylpiperazin-1-yl)propoxy substitution at position 4 of 3-phenylcoumarins (compound 36) exhibited significant antibacterial and antifungal activity as that of standard streptomycin and itrazole, respectively [116]. Finally, compounds with benzofuro[3,2b]pyridine core at the position 6 of the scaffold have been evaluated against S. aureus, B. subtilis, Escherichia coli, Salmonella typhi, Candida albicans, Aspergillus niger and Mycobacterium tuberculosis H37Rv, and exhibited promising activities, with compound 37 being the best compound within the series [117].…”