3-Phenylcoumarin

3-Phenylcoumarin

Names
IUPAC name 3-phenylchromen-2-one
Other names 3-phenyl-2H-chromen-2-one
Identifiers
CAS Number	955-10-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL510349
ChemSpider	63565
ECHA InfoCard	100.012.248
EC Number	213-473-5
PubChem CID	70385
UNII	WV24YNY4AU
CompTox Dashboard (EPA)	DTXSID50241860
InChI InChI=1S/C15H10O2/c16-15-13(11-6-2-1-3-7-11)10-12-8-4-5-9-14(12)17-15/h1-10H Key: HWDSXZLYIKESML-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C2=CC3=CC=CC=C3OC2=O
Properties
Chemical formula	C15H10O2
Molar mass	222.243 g·mol−1
Structure
Crystal structure	Monoclinic [1]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312+P330, P501
Safety data sheet (SDS)	Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Phenylcoumarin or 3-phenylchromen-2-one is a chemical compound that has the molecular formula C₁₅H₁₀O₂. ^[2] A member of the coumarin compound family, its derivatives have been investigated for pharmacological applications, including in enzyme inhibition ^[3] and as anticancer agents. ^{[4] [5]}

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. ^[5] 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. ^[3]

References

1. Matos, Maria J.; Santana, Lourdes; Uriartea, Eugenio (September 2012). "3-Phenylcoumarin". Acta Crystallographica Section E. 68 (9): o2645. Bibcode:2012AcCrE..68o2645M. doi:10.1107/S1600536812034277. ISSN   2056-9890. PMC   3435673 . PMID   22969544.
2. "3-Phenylcoumarin". PubChem. National Library of Medicine. Retrieved June 10, 2024.
3. 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. 21 (11): 3342–3345. doi:10.1016/j.bmcl.2011.04.012. PMID   21514152.
4. 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. Bibcode:2018FrCh....6...41R. doi: 10.3389/fchem.2018.00041 . ISSN   2296-2646. PMC   5840146 . PMID   29552556.
5. 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. 26 (21): 6755. doi: 10.3390/molecules26216755 . ISSN   1420-3049. PMC   8587835 . PMID   34771164.