| Autor: |
Obydennov KL; Ural Federal University, 19 Mira Str., Ekaterinburg 620002, Russia., Kalinina TA; Ural Federal University, 19 Mira Str., Ekaterinburg 620002, Russia., Galieva NA; Ural Federal University, 19 Mira Str., Ekaterinburg 620002, Russia., Beryozkina TV; Ural Federal University, 19 Mira Str., Ekaterinburg 620002, Russia., Zhang Y; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.; Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, P. R. China., Fan Z; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.; Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, P. R. China., Glukhareva TV; Ural Federal University, 19 Mira Str., Ekaterinburg 620002, Russia.; Postovsky Institute of Organic Synthesis UB RAS, 22 Sofia Kovalevskaya Str., Ekaterinburg 620990, Russia., Bakulev VA; Ural Federal University, 19 Mira Str., Ekaterinburg 620002, Russia. |
| Abstrakt: |
This work deals with the synthesis and evaluation of fungicidal activity of benzimidazole derivatives, which are structural analogues of commercial anti-tubulin fungicides. A number of N -acyl and N -thioacyl derivatives of 2-amino-1 H -benzo[ d ]imidazole were prepared, and their fungicidal activity against 13 strains of phytopathogenic fungi was studied. The most active compounds against the majority of the studied strains were 3a , 4l , and 4o , and the EC 50 values of these compounds were in the range 2.5-20 μg/mL. Compound 3a showed the highest activity against the P. infestans strain, the growth of which is not suppressed by carbendazim. The formation of ligand-receptor complexes of various tautomeric forms of the studied benzimidazoles with homologous models of β-tubulins of B. cinerea , F. oxysporum , and P. infestans was modeled. Induced fit docking has been used for the simulation. The obtained data suggest the possibility of binding of benzimidazole fungicides to β-tubulin in the ″nocodazole cavity″ in the tautomeric form bearing a double exocyclic C═N bond. The importance of the formation of hydrogen bonds of benzimidazoles with the amino acid residue Val236 along with the Glu198 residue is also revealed in the present study. |
