Preparation and Antiviral Activity of Some New C3- and CS-Symmetrical Tri-Substituted Triazine Derivatives Having Benzylamine Substituents

• Published in: Chemical & pharmaceutical bulletin Vol. 66; no. 8; pp. 830 - 838
• Main Authors: Mibu, Nobuko, Yokomizo, Kazumi, Sano, Marina, Kawaguchi, Yuuna, Morimoto, Kenta, Shimomura, Syunsuke, Sato, Ryo, Hiraga, Nozomi, Matsunaga, Aya, Zhou, Jian-Rong, Ohata, Tomonori, Aki, Hatsumi, Sumoto, Kunihiro
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 01.08.2018; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: 1,3,5-triazine; anti-herpes simplex virus type 1; Antiviral activity; Benzene; benzylamine-substituent; C3-symmetry; Cytotoxicity; Derivatives; Herpes simplex; Herpes viruses; hydrogen bond donor; structure–activity relationship; Toxicity; Triazine; Vero cells; Viruses
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c18-00274

We report the preparation of new C3- and CS-symmetrical molecules constructed on a triazine (TAZ) template. Anti-herpes simplex virus type 1 (anti-HSV-1) and cytotoxic activities against Vero cells of synthesized TAZ derivatives were evaluated. The results suggested that the presence of an electron-donating group(s) on the benzene ring in benzylamine groups on the TAZ template is an important structural factor for expressing a high level of anti-HSV-1 activity and low cytotoxicity for these C3 types of TAZ derivatives. Among the tested TAZ derivatives, compounds 4f and 7h showed the highest anti HSV-1 activities (EC50=0.98 and 1.23 µM, respectively) and low cytotoxic activities to Vero cells (50% cytotoxic concentration (CC50)=292.2 and >200 µM, respectively).