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

Chem Pharm Bull (Tokyo). 2018;66(8):830-838. doi: 10.1248/cpb.c18-00274.

Abstract

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).

Keywords: 1,3,5-triazine; C3-symmetry; anti-herpes simplex virus type 1; benzylamine-substituent; hydrogen bond donor; structure–activity relationship.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Benzylamines / chemical synthesis*
  • Benzylamines / pharmacology
  • Cell Survival / drug effects
  • Chlorocebus aethiops
  • Drug Design
  • Herpesvirus 1, Human / drug effects*
  • Humans
  • Structure-Activity Relationship
  • Triazines / chemical synthesis*
  • Triazines / pharmacology
  • Vero Cells

Substances

  • Antiviral Agents
  • Benzylamines
  • Triazines