Synthesis and antiviral activity of N-adamantyl-2-amino(or 2-phenoxy)-acylamides

• Published in: Chemical research in Chinese universities Vol. 29; no. 4; pp. 706 - 709
• Main Authors: Liu, Dan, Fan, Zi-chen, Jiang, Jia-mei, Wei, Jing, Xin, Jian-chuang
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.08.2013; Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology,Shenyang 110142, P.R.China%School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P.R.China
• Subjects: Analytical Chemistry; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Inorganic Chemistry; Organic Chemistry; Physical Chemistry; Adamantyl-2-amino(or 2-phenoxy)-acylamide; M2 proton channel; Antiviral activity; N-Adamantyl-2-amino(or 2-phenoxy)-acylamide
• ISSN: 1005-9040; 2210-3171
• DOI: 10.1007/s40242-013-2380-8

New N -adamantyl-2-amino-acylamides( 3 a– 3 f) and N -adamantyl-2-phenoxy-acetamides( 6 a– 6 d) were designed and synthesized by the modification of the amino group of amantadine 1 and the structures were confirmed by mass spectra(MS) and 1 H NMR spectra. The antiviral potencies of the synthesized compounds were evaluated against the replication of influenza virus A/H 3 N 2 subtype in Madin-Darby canine kidney(MDCK) cells. Among the amantadine derivatives, compound 3 a 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.