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Paper | Regular issue | Vol 98, No. 4, 2019, pp.489-508
Published online, 25th March, 2019
DOI: 10.3987/COM-19-14052
Preparation of Some Novel Trisubstituted 1,3,5-Triazines and Hybrid Linker Mode 1,3,5-Triazine Derivatives and Their Biological Evaluation

Nobuko Mibu, Kazumi Yokomizo, Kanae Yamada, Junko Matsuyama, Syoko Tomonaga, Izumi Sakai, Ryo Sato, Yuki Kawano, Yumemi Matsumoto, Yuka Fujita, Yusuke Inoue, Masaya Iida, Kaneto Hashiguchi, Jian-Rong Zhou, Makoto Furutachi, and Kunihiro Sumoto*

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


We report a new route to the preparation of C3-symmetrical multivalent hybrid-type molecules having a tris-aminoethylamine (TAEA) linker group and 1,3,5-triazine recognition moieties in the molecule and we also report the results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. Among the tested compounds, a new mid-size C2-symmetrical multivalent hybrid-type molecule (10aq) showed a high level of anti-HSV-1 activity (EC50 = 19.7 μM) with low cytotoxicity (CC50 > 200 μM) against Vero cells. A new CS-symmetrical multivalent derivative (4ab) also showed high anti-HSV-1 activity (EC50 = 1.77 μM) with low cytotoxicity (CC50 > 200 μM). The hybrid-type C2-symmetrical multivalent mid-size molecule (10aq) seems to be an interesting new lead in the search for new hybrid-type symmetrical multivalent antiviral compounds.