Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (1): 76-81.doi: 10.1007/s40242-012-2064-9

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Synthesis and Antitussive Effect of New Hydantoin Compounds

ZHANG Qun-li1, SONG Li-jun2, WANG En-si1,3   

  1. 1. College of Life Science, Jilin University, Changchun 130021, P. R. China;
    2. The First Hospital, Jilin University, Changchun 130021, P. R. China;
    3. College of Pharmacy, Jilin University, Changchun 130021, P. R. China
  • Received:2012-02-21 Revised:2012-03-31 Online:2013-02-01 Published:2013-01-23

Abstract:

A series of new hydantoin compounds was synthesized with 3-bromo phenylacetic acid and 3,4-dimethylbromobenzene as starting material, 7-bromo-2-tetralone and 2-bromo-5,6,8,9-tetrahydro-7-benzocyclo- heptenone as intermediate and Ullmann reaction, Suzuki reaction and Bucherer-Berg's reaction as key steps. The structures of the key intermediate and target compounds were confirmed by 1H NMR, 13C NMR, IR and MS. Bioactivity research showed that target compounds 6a, 6c, 6d, 6e and 15i had significant antitussive effect on the ammonia-induced cough of mice.

Key words: Hydantoin, 2-Bromo-5,6,8,9-tetrahydro-7-benzocycloheptenone, Bioactivity, 7-Bromo-2-tetralone, Antitussive effect