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Paper | Regular issue | Vol 94, No. 9, 2017, pp.1653-1677
Published online, 12th July, 2017
DOI: 10.3987/COM-17-13735
■ Antiviral Activities of Some New 2,4,6-Trisubstituted 1,3,5-Triazines Having Alkoxy and/or Alkylamino Groups

Nobuko Mibu, Kazumi Yokomizo, Ai Yuzuriha, Marie Otsubo, Yuna Kawaguchi, Marina Sano, Izumi Sakai, Keita Nakayama, Jian-Rong Zhou, and Kunihiro Sumoto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

We report the preparation of C3- and CS-symmetrical 2,4,6-trisubstituted 1,3,5-triazine derivatives having alkoxy and/or alkylamino groups and results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. New targeted symmetrical molecules were obtained by using a method starting with 2,4,6-trichloro-1,3,5-triazine (1). Among the synthesized compounds, CS-symmetrical tri-aliphatic alkylamino-substituted compound 6s showed high anti-HSV-1 activity (EC50 = 5.4 μM) and low cytotoxicity (CC50 > 200 μM). The results of an SAR study suggested that the presence of two hydrogen bond donor protons of sec-amine functionality in the molecule is an important structural factor for expression of potential anti-HSV-1 activities.