Discovery of benzotriazole-azo-phenol/aniline derivatives as antifungal agents

Bioorg Med Chem Lett. 2018 Jan 15;28(2):181-187. doi: 10.1016/j.bmcl.2017.11.032. Epub 2017 Nov 16.

Abstract

A series of benzotriazole-azo-phenol/aniline derivatives were prepared and evaluated for their antifungal activities against six phytopathogenic fungi such as Fusarium graminearum, Fusarium solani, Alternaria alternate, Valsa mali, Botrytis cinerea, and Curvularia lunata. Among them, compounds IIf, IIn, and IIr showed a broad-spectrum of potent antifungal activities. Especially some compounds displayed 3.5-10.8 folds more potent activities than carbendazim against A. alternata and C. lunata. Notably, compounds IIc, IIm, and IIr exhibited good protective and therapeutic effects against B. cinerea at 200 μg/mL. Their structure-activity relationships were also discussed.

Keywords: Antifungal activity; Benzotriazole; Benzotriazole-azo-aniline; Benzotriazole-azo-phenol; Protective effects; Therapeutic effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Azo Compounds / chemistry
  • Azo Compounds / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Discovery
  • Fungi / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Structure-Activity Relationship
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Aniline Compounds
  • Antifungal Agents
  • Azo Compounds
  • Phenols
  • Triazoles
  • benzotriazole
  • aniline