Synthesis, biological activity and structure activity relationship studies of novel conazole analogues via conventional, microwave and ultrasound mediated techniques

Bioorg Chem. 2018 Dec:81:55-70. doi: 10.1016/j.bioorg.2018.07.036. Epub 2018 Aug 1.


1,2,4-Triazole derivatives containing a piperazine nucleus (4a-d and 10) were prepared starting from 1-(2-methoxyphenyl)piperazine or ethyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate via several steps. The synthesis of fifteen compounds (7a-l and 13a-c), which can be considered as new analogues of azole class antifungals was performed starting from 1,2,4-triazoles (4a-d and 10) via three steps containing the condensation with 2-bromo-1-(4-chlorophenyl)ethanone, reduction of carbonyl group to alcohol and alkylation of OH group, respectively. All the reactions were examined under conventional, ultrasound and microwave irradiation conditions as green chemistry techniques, and optimum conditions were defined. The newly synthesized compounds were screened for their biological potentials including antimicrobial, antioxidant, antiurease and anti α-glucosidase activities and promising results were obtained. The enzyme inhibitory potentials of these compounds were further validated through molecular docking.

Keywords: Antimicrobial; Antioxidants; Conazole; Microwave irradiation; Molecular docking; Ultrasound sonication; Urease activity; α-Glucosidase activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Azoles / chemical synthesis
  • Azoles / chemistry
  • Azoles / pharmacology*
  • Bacteria / drug effects
  • Canavalia / enzymology
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Microwaves*
  • Molecular Docking Simulation
  • Molecular Structure
  • Structure-Activity Relationship
  • Ultrasonic Waves*
  • Urease / antagonists & inhibitors
  • Urease / metabolism
  • alpha-Glucosidases / metabolism


  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antioxidants
  • Azoles
  • Enzyme Inhibitors
  • alpha-Glucosidases
  • Urease