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XIAO Qiong, LIU Chang, YIN Dali. Synthesis of a new metabolite of buagarofuran(AF-5)[J]. Journal of China Pharmaceutical University, 2016, 47(6): 673-677. DOI: 10.11665/j.issn.1000-5048.20160607
Citation: XIAO Qiong, LIU Chang, YIN Dali. Synthesis of a new metabolite of buagarofuran(AF-5)[J]. Journal of China Pharmaceutical University, 2016, 47(6): 673-677. DOI: 10.11665/j.issn.1000-5048.20160607

Synthesis of a new metabolite of buagarofuran(AF-5)

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  • It has been reported that buagarofuran(AF-5)as an anxiolytic drug. It possesses a structural feature including α-agarofuran and the n-butyl side chain. Recently, there is a new metabolite found in clinical study, which is hypothesized that the n-butyl side chain has been oxidized to carboxylic acid. In order to confirm its structure, the target compound was prepared from(4aR, 7R, 8aR)-8a-hydroxy-7-(2-hydroxypropan-2-yl)-4a-methyloctahydronaphthalen-2(1H)-one in a six-step reaction with an overall yield of 16. 7%. The structure is confirmed by NMR and MS.
  • [1]
    Guo JY.Agarofuan derivatives,their preparation,pharmaceutical composition containing them and their use as medicine:CN,98122447[P].2002-11-26.
    [2]
    Guo JY. New agarofuran derivatives, their preparations, pharma-
       ceutical compositions containing them and their uses as medicaments:CN,00108339[P].2000-05-12.
    [3]
    Guo JY.Dehydrobaimuxinol derivatives use as medicaments for treating or preventing regressive diseases of brain:CN,00108338[P].2000-05-12.
    [4]
    Ji M.Synthesis of metablism product of cloxazolam 7-chloro-5-o-chlorophenyl -1,3-dihydro-1,4-benzodiazepin-2-one[J].J China Pharm Univ(中国药科大学学报),1993,24(3):180-181.
    [5]
    Li C,Zhang WY,Guo JY,et al.Studies on agarofurans VIII.Synthesis of the metabolites of 4-butyl-α-agarofuran[J].Chin Chem Lett,2002,13(1):19-22.
    [6]
    Li C,Yin DL,Huang HQ,et al.New stereoselective synthesis of 4-butyl-α-agarofuran[J].Chin Chem Lett,2003,14(9):881-882.
    [7]
    Chandrasekhar S,Babu GSK,Mohapatra DK.Practical syntheses of(2S)-R207910 and(2R)-R207910[J].Eur J Org Chem,2011,2011(11):2057-2061.
    [8]
    Berthelette C.Nitric oxide releasing prodrugs of diaryl-2-(5H)-furanones as cyclooxygenase-2 inhibitors:US,176331[P].2004-09-09.
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