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Efaroxan

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Efaroxan
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 2-(2-ethyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
  • N\1=C(\NCC/1)C3(Oc2ccccc2C3)CC
  • InChI=1S/C13H16N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-6H,2,7-9H2,1H3,(H,14,15) checkY
  • Key:RATZLMXRALDSJW-UHFFFAOYSA-N checkY
  (verify)

Efaroxan is anα2-adrenergic receptorantagonist[1] andantagonist of theimidazoline receptor.

Synthesis

[edit]
Synthesis (Cmp#13):[2] Revised:[3][4]

TheDarzens reaction between 2-fluorobenzaldehyde [57848-46-1] (1) and Ethyl 2-bromobutyrate [533-68-6] (2) gives ethyl 2-ethyl-3-(2-fluorophenyl)oxirane-2-carboxylate,CID:100942311 (3). A catalytic hydrogenation over Pd/C would give ethyl 2-[(2-fluorophenyl)methyl]-2-hydroxybutanoate,CID:77591056 (4).Saponification of the ester then gives 2-[(2-Fluorophenyl)methyl]-2-hydroxybutanoic acid,CID:53869347 (5). Treatment with 2 molar equivalents ofsodium hydride apparently gives 2-Ethyl-2,3-dihydrobenzofuran-2-carboxylic acid [111080-50-3] (6). Treatment of the carboxylic acid withthionyl chloride then gives the acid chloride and subsequent treatment of this withethylenediamine in the presence of trimethylaluminium completed the synthesis ofEfaroxan (8).

See also

[edit]

References

[edit]
  1. ^Chopin P, Colpaert FC, Marien M (February 1999)."Effects of alpha-2 adrenoceptor agonists and antagonists on circling behavior in rats with unilateral 6-hydroxydopamine lesions of the nigrostriatal pathway".J. Pharmacol. Exp. Ther.288 (2):798–804.PMID 9918591.
  2. ^Chapleo, Christopher B.; Myers, Peter L.; Butler, Richard C. M.; Davis, John A.; Doxey, John C.; Higgins, Stanley D.; Myers, Malcolm; Roach, Alan G.; Smith, Colin F. C. (1984). ".alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity". Journal of Medicinal Chemistry 27 (5): 570–576. doi:10.1021/jm00371a003.
  3. ^Mayer, P.; Brunel, P.; Imbert, T. (1999). "A new efficient synthesis of efaroxan". Bioorganic & Medicinal Chemistry Letters 9 (20): 3021–3022. doi:10.1016/S0960-894X(99)00531-4.
  4. ^Couture, K.; Gouverneur, V.; Mioskowski, C. (1999). "A new approach to the synthesis of efaroxan". Bioorganic & Medicinal Chemistry Letters 9 (20): 3023–3026. doi:10.1016/S0960-894X(99)00530-2.

External links

[edit]
  • Media related toEfaroxan at Wikimedia Commons
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
IRTooltip Imidazoline receptor


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