3-Phenylcoumarin Explained

3-Phenylcoumarin or 3-phenylchromen-2-one is a chemical compound that has the molecular formula .[1] A member of the coumarin compound family, its derivatives have been investigated for pharmacological applications, including in enzyme inhibition[2] and as anticancer agents.[3] [4]

Synthesis

3-Phenylcoumarins have been synthesized through various means, starting with different precursors and catalysts with goals of achieving better yield, different conditions of the final product for producing derivatives, ease of purification, lower toxicity or environmental impact, or other considerations. One synthetic method is done via Perkin reaction in dimethyl sulfoxide from methoxy-substituted phenylacetic acid and methoxy- or ethoxy-substituted salicylaldehyde using the dehydrating agent dicyclohexylcarbodiimide.

Notes and References

  1. Web site: 3-Phenylcoumarin . National Library of Medicine . PubChem . June 10, 2024.
  2. Matos . Maria João . Santana . Lourdes . Uriarte . Eugenio . Delogu . Giovanna . Corda . Marcella . Fadda . Maria Benedetta . Era . Benedetta . Fais . Antonella . June 2011 . New halogenated phenylcoumarins as tyrosinase inhibitors . Bioorganic & Medicinal Chemistry Letters . en . 21 . 11 . 3342–3345 . 10.1016/j.bmcl.2011.04.012. 21514152 .
  3. Rauhamäki . Sanna . Postila . Pekka A. . Niinivehmas . Sanna . Kortet . Sami . Schildt . Emmi . Pasanen . Mira . Manivannan . Elangovan . Ahinko . Mira . Koskimies . Pasi . Nyberg . Niina . Huuskonen . Pasi . Multamäki . Elina . Pasanen . Markku . Juvonen . Risto O. . Raunio . Hannu . 2018-03-02 . Structure-Activity Relationship Analysis of 3-Phenylcoumarin-Based Monoamine Oxidase B Inhibitors . Frontiers in Chemistry . 6 . 41 . 10.3389/fchem.2018.00041 . 2296-2646 . 5840146 . 29552556 . free.
  4. Matos . Maria J. . Uriarte . Eugenio . Santana . Lourdes . 2021-11-08 . 3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade . Molecules . en . 26 . 21 . 6755 . 10.3390/molecules26216755 . 1420-3049 . 8587835 . 34771164 . free.

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