The Darzens 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 of sodium hydride apparently gives 2-Ethyl-2,3-dihydrobenzofuran-2-carboxylic acid [111080-50-3] (6). Treatment of the carboxylic acid with thionyl chloride then gives the acid chloride and subsequent treatment of this with ethylenediamine in the presence of trimethylaluminium completed the synthesis of Efaroxan (8).
^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.
^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.
^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.
^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.
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efaroxan, adrenergic, receptor, antagonist, antagonist, imidazoline, receptor, clinical, dataroutes, ofadministrationoralatc, codenonelegal, statuslegal, statusin, general, uncontrolledidentifiersiupac, name, ethyl, dihydro, benzofuran, dihydro, imidazolecas, . Efaroxan is an a2 adrenergic receptor antagonist 1 and antagonist of the imidazoline receptor EfaroxanClinical dataRoutes ofadministrationOralATC codenoneLegal statusLegal statusIn general uncontrolledIdentifiersIUPAC name 2 2 ethyl 2 3 dihydro 1 benzofuran 2 yl 4 5 dihydro 1H imidazoleCAS Number89197 32 0 YPubChem CID72016ChemSpider65015 YUNIIG00490L21HChEMBLChEMBL57895 YCompTox Dashboard EPA DTXSID8045149Chemical and physical dataFormulaC 13H 16N 2OMolar mass216 284 g mol 13D model JSmol Interactive imageSMILES N 1 C NCC 1 C3 Oc2ccccc2C3 CCInChI 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 YKey RATZLMXRALDSJW UHFFFAOYSA N Y verify Contents 1 Synthesis 2 See also 3 References 4 External linksSynthesis edit nbsp Synthesis Cmp 13 2 Revised 3 4 The Darzens 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 of sodium hydride apparently gives 2 Ethyl 2 3 dihydrobenzofuran 2 carboxylic acid 111080 50 3 6 Treatment of the carboxylic acid with thionyl chloride then gives the acid chloride and subsequent treatment of this with ethylenediamine in the presence of trimethylaluminium completed the synthesis of Efaroxan 8 See also editFluparoxan IdazoxanReferences edit 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 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 Mayer P Brunel P Imbert T 1999 A new efficient synthesis of efaroxan Bioorganic amp Medicinal Chemistry Letters 9 20 3021 3022 doi 10 1016 S0960 894X 99 00531 4 Couture K Gouverneur V Mioskowski C 1999 A new approach to the synthesis of efaroxan Bioorganic amp Medicinal Chemistry Letters 9 20 3023 3026 doi 10 1016 S0960 894X 99 00530 2 External links edit nbsp Media related to Efaroxan at Wikimedia Commons nbsp This pharmacology related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Efaroxan amp oldid 1117773985, wikipedia, wiki, book, books, library,
