Thermodynamic Studies on 4-Aminocoumarin tautomers

The reaction of 4‐aminocoumarin (2) with benzaldehyde gave the bisenamino derivatives 4. Thus, transamination of 2 with o‐phenylenediamine furnished enamino skeleton 3, which can be obtained from 1. Reaction of 1 with 5‐aminoisoxazole afforded 5. While reaction of 2 with benzalaniline, isatinanil and phenyl isothio cyanate afforded the corresponding 7, 8 and 9, respectively. Heterocyclic annulations of 2‐phenylthiazolidine‐4‐one 10 2‐phenylthiazolidin‐4‐one 10 and 2‐phenyl‐thiazinan‐4‐one 11 systems were achieved via reaction of 2 with benzaldehyde and rather either 2‐mercaptoacetic acid or 3‐mercaptopropanoic acid respectively. The behavior of 2 towards monochloro acetic acid and 4‐oxo‐4‐phenylbuatonic 4‐Oxo‐4‐phenylbutanoic acid was investigated. All of the newly synthesized compounds were evaluated as antitumor (cytotoxic) agents. Most of these compounds have shown significant antitumor activities.

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Chemoselective Synthesis of Enamino‐Coumarin Derivatives Identified as Potent Antitumor Agents

Ibrahim

Hamama

Metwalli

et al. 2015

Journal of Heterocyclic Chem

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Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

et al. 2019

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Facile and efficient syntheses of 4‐(1H‐pyrrol‐1‐yl)‐coumarins and 6‐(1H‐pyrrol‐1‐yl)‐coumarins from the corresponding aminocoumarins are reported. The transformations were optimized and their corresponding scope and limitations were assessed. Selected (1H‐pyrrol‐1‐yl)‐coumarins were further subjected to a mild thiocyanation, undergoing selective functionalization on the pyrrole nucleus. A set of 10 differently substituted compounds was submitted to activity testing against various fungal strains. It was found that the introduction of a SCN moiety increased the antifungal activity, turning some compounds into fungicidal agents, to the point that one of the thiocyanato derivatives displayed an antifungal profile comparable to those of fluconazole and nystatin.

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Synthesis of new coumarins complemented by quantum chemical studies

et al. 2015

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Thermodynamic Studies on 4-Aminocoumarin tautomers

Cited by 11 publications

References 19 publications

Chemoselective Synthesis of Enamino‐Coumarin Derivatives Identified as Potent Antitumor Agents

Chemoselective Synthesis of Enamino‐Coumarin Derivatives Identified as Potent Antitumor Agents

Synthesis and Antifungal Activity of 4‐ and 6‐(1H‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

Synthesis of new coumarins complemented by quantum chemical studies

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