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

Abstract

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 αaminophosphonates 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 oxysporum and Botrytis cinerea by 65% to 84% with IC50 values less than 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 compound 4l. These findings suggest a possible use of these compounds as synthetic pesticides with less hazardous effects with antioxidant, and anti-tyrosinase properties.

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

“…[34] The α-aminophosphonates hold a prominent place in chemical synthesis, they have described various synthetic methods via multicomponents Kabachnik-Fields reaction, [35][36] using various catalysts. [37][38][39][40][41][42] Herein, we have developed a novel procedure for the synthesis of series of α-aminophosphonates using the commercial SB-2 cationic resin as eco-friendly and reusable organocatalyst. The use of the cationic exchange resins as catalyst has been previously reported in otherorganic reactions.…”

“…The α ‐aminophosphonates were previously evaluated against various multidrug‐resistant fungi; such as: Scedosporium Species , [32] Lomentosporaprolificans , [33] Phomopsisasparagi, Fusariumoxysporum and Botrytis cinerea [34] . The α‐ aminophosphonates hold a prominent place in chemical synthesis, they have described various synthetic methods via multicomponents Kabachnik‐Fields reaction, [35–36] using various catalysts [37–42] …”

Novel bidentate N-coordinated alkylaluminum complexes: synthesis, characterization, and efficient catalysis for hydrophosphonylation

“…α-Amino phosphonates have a very wide range of pharmacological and physiological effects, [48][49][50] and they are widely used in the synthesis of pharmaceuticals and pesticides. [51][52][53][54][55][56][57][58][59][60][61] In addition, α-amino phosphonates are used as key reaction intermediates, organic catalysts, and chelating groups in tridentate ligands. [62][63][64][65][66][67] Among the various synthetic methods for α-amino phosphonates, the Pudovik reaction 68 (nucleophilic addition of dialkylphosphites to imines) is one of the most general and straightforward methods.…”

Full factorial optimization of α-aminophosphonates synthesis using diphenylphosphinic acid as efficient organocatalyst

“…The α-aminophosphonates represent, from its discovery by Kabachnik-Fields in 1952 [4-5] to nowadays an important class of organophosphorus compounds due to their analogs amino acid, and mimic transition states of active peptides [6][7][8]. The α-aminophosphonates show an outstandingly broad spectrum of pharmacological and physiological effectiveness [9][10][11], and they are used as inhibitors of the angiotensin-converting enzyme [12], antiviral [13], antibiotic [14], antibacterial [15], antitumoral [16], anti-HIV [17], antihypertensive [18], anti-tuberculosis agents [19], antioxidant [20][21], anticorrosion [22], herbicides, fungicides and insecticides [23][24]. In reactivity terms, the α-aminophosphonates are used as a key intermediate in HWE reaction [25], as organocatalyst in the Petasis Boronic Acid Mannich reaction [26], in asymmetric Michael addition [27], and for the preparation of complexes as tridentate ligands [28].…”