CRCU

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (4): 706-709.doi: 10.1007/s40242-013-2380-8

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Synthesis and Antiviral Activity of N-Adamantyl-2- amino(or 2-phenoxy)-acylamides

LIU Dan1, FAN Zi-chen1, JIANG Jia-mei1, WEI Jing2, XIN Jian-chuang1   

  1. 1. Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142, P. R. China;
    2. School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. China
  • Received:2012-10-09 Revised:2012-11-04 Online:2013-08-01 Published:2013-07-15
  • Contact: LIU Dan E-mail:Liudan1971@hotmail.com
  • Supported by:

    Supported by the Scientific Research Foundation for PhD of Shenyang University of Chemical Technology, China (No.200807).

Abstract:

New N-adamantyl-2-amino-acylamides(3a―3f) and N-adamantyl-2-phenoxy-acetamides(6a―6d) were designed and synthesized by the modification of the amino group of amantadine 1 and the structures were confirmed by mass spectra(MS) and 1H NMR spectra. The antiviral potencies of the synthesized compounds were evaluated against the replication of influenza virus A/H3N2 subtype in Madin-Darby canine kidney(MDCK) cells. Among the amantadine derivatives, compound 3a had the strongest antiviral potency and showed activity similar to that of amantadine. Interestingly, the bulky and extended lipophilic moieties on the α-position of the carbonyl group resulted in decreases in potency.

Key words: N-Adamantyl-2-amino(or 2-phenoxy)-acylamide, Antiviral activity, M2 proton channel