Acifran

Acifran

Names
IUPAC name 5-Methyl-4-oxo-5-phenyl-4,5-dihydro-2-furancarboxylic acid
Systematic IUPAC name 5-Methyl-4-oxo-5-phenyl-4,5-dihydro-2-furancarboxylic acid
Identifiers
CAS Number	72420-38-3
ChEMBL	ChEMBL278488
ChemSpider	46712
IUPHAR/BPS	1595
Jmol 3D model	Interactive image
KEGG	D02753
PubChem	51576
InChI InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15) Key: DFDGRKNOFOJBAJ-UHFFFAOYSA-N InChI=1/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15) Key: DFDGRKNOFOJBAJ-UHFFFAOYAE
SMILES CC1(C(=O)C=C(O1)C(=O)O)C2=CC=CC=C2
Properties
Chemical formula	C12H10O4
Molar mass	218.21 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acifran is a niacin receptor agonist.^[1]

Synthesis

Acifran synthesis:^[2]

It is synthesized from acetophenone and the anion of 1-methyl-2,6-dithiolane (2) (prepared using BuLi). The latter is a reversed polarity version of acetaldehyde (Umpolung) whose condensation with 1 produces tertiary alcohol 3 by carbonyl addition. Acid-catalyzed dithiolane exchange with pyruvate leads to α-hydroxyketone 4. This last undergoes base-catalyzed oxylation on the methyl ketone moiety and cyclodehydration and ester hydrolysis to produce acifran 5.

References

1. Jung, J. K.; Johnson, B. R.; Duong, T; Decaire, M; Uy, J; Gharbaoui, T; Boatman, P. D.; Sage, C. R.; Chen, R; Richman, J. G.; Connolly, D. T.; Semple, G (April 2007). "Analogues of acifran: agonists of the high and low affinity niacin receptors, GPR109a and GPR109b". J. Med. Chem. 50 (7): 1445–8. doi:10.1021/jm070022x. PMID 17358052.
2. Cayen, M. N.; Gonzalez, R.; Ferdinandi, E. S.; Greselin, E.; Hicks, D. R.; Kraml, M.; Dvornik, D. (1986). "The metabolic disposition of acifran, a new antihyperlipidemic agent, in rats and dogs". Xenobiotica 16 (3): 251. doi:10.3109/00498258609043528. PMID 3705621.