Fiaud's Acid, a novel organocatalyst for diastereoselective bis α-aminophosphonates synthesis with in-vitro biological evaluation of antifungal, antioxidant and enzymes inhibition potential

Rim Aissa; Samia Guezane-Lakoud; Martial Toffano; Lynda Gali; Louisa Aribi-Zouioueche

doi:10.1016/j.bmcl.2021.128000

Fiaud's Acid, a novel organocatalyst for diastereoselective bis α-aminophosphonates synthesis with in-vitro biological evaluation of antifungal, antioxidant and enzymes inhibition potential

Bioorg Med Chem Lett. 2021 Jun 1:41:128000. doi: 10.1016/j.bmcl.2021.128000. Epub 2021 Mar 30.

Authors

Rim Aissa¹, Samia Guezane-Lakoud², Martial Toffano³, Lynda Gali⁴, Louisa Aribi-Zouioueche¹

Affiliations

¹ Ecocompatible Asymmetric Catalysis Laboratory (LCAE) Badji Mokhtar Annaba-University, B.P 12, 23000 Annaba, Algeria.
² Ecocompatible Asymmetric Catalysis Laboratory (LCAE) Badji Mokhtar Annaba-University, B.P 12, 23000 Annaba, Algeria. Electronic address: [email protected].
³ Equipe de Catalyse Moléculaire-ICMMO Bât 420, Université Paris- Saclay, France.
⁴ Research Center in Biotechnology, Ali Mendjli Nouvelle Ville UV 03, BP E73 Constantine, Algeria.

PMID: 33798702
DOI: 10.1016/j.bmcl.2021.128000

Abstract

(S, S)-1-hydroxy-1-oxo-2-c,5-t-diphenylphospholane or Fiaud's acid is used as a novel and effective chiral organocatalyst for bis α-aminophosphonates synthesis with excellent diastereoselectivity and yields within short reaction time. All synthesized bis α-aminophosphonates revealed a good to excellent antifungal capacity, where the six compounds 4a, 4b, 4e, 4h, 4k and 4l are the best fungicide inhibiting the growth of Fusarium oxysporumandBotrytis cinereaby 65% to 84% with IC₅₀ values <0.02 mg/mL. Similarly, these six products exhibited a strong antioxidant effect, whereas a low inhibition activity was obtained with both AChE and BChE. Furthermore, they displayed a very weak inhibitory activity against tyrosinase except for the compound4l.These findings suggest a possible use of these compounds as synthetic pesticides with less hazardous effects with antioxidant, and anti-tyrosinase properties.

Keywords: Bis α-aminophosphonates; Chiral organocatalyst; Cholinesterase; Fiaud’s acid; Tyrosinase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / metabolism
Animals
Antifungal Agents / chemical synthesis
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Antioxidants / chemical synthesis
Antioxidants / chemistry
Antioxidants / pharmacology*
Benzothiazoles / antagonists & inhibitors
Biphenyl Compounds / antagonists & inhibitors
Botrytis / drug effects
Butyrylcholinesterase / metabolism
Cholinesterase Inhibitors / chemical synthesis
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / pharmacology*
Dose-Response Relationship, Drug
Electrophorus
Fusarium / drug effects
Horses
Microbial Sensitivity Tests
Molecular Structure
Picrates / antagonists & inhibitors
Structure-Activity Relationship
Sulfonic Acids / antagonists & inhibitors

Substances

Antifungal Agents
Antioxidants
Benzothiazoles
Biphenyl Compounds
Cholinesterase Inhibitors
Picrates
Sulfonic Acids
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
1,1-diphenyl-2-picrylhydrazyl
Acetylcholinesterase
Butyrylcholinesterase

Supplementary concepts

Botrytis cinerea
Fusarium oxysporum