Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates

Abstract

A series of novel α-furfuryl-2-alkylaminophosphonates have been efficiently synthesized from the one-pot threecomponent classical Kabachnik−Fields reaction in a green chemical approach by addition of an in situ generated dialkylphosphite to Schiff's base of aldehydes and amines by using environmental and eco-friendly silica gel supported iodine as a catalyst by microwave irradiation. The advantage of this protocol is simplicity in experimental procedures and products were resulted in high isolated yields. The synthesized α-furfuryl-2alkylaminophosphonates were screened to in vitro antioxidant and plant growth regulatory activities and some are found to be potent with antioxidant and plant growth regulatory activities. These in vitro studies have been further supported by ADMET (absorption, distribution, metabolism, excretion, and toxicity), quantitative structure−activity relationship, molecular docking, and bioactivity studies and identified that they were potentially bound to the GLN340 amino acid residue in chain C of 1DNU protein and TYR597 amino acid residue in chain A of 4M7E protein, causing potential exhibition of antioxidant and plant growth regulatory activities. Eventually, title compounds are identified as good blood− brain barrier (BBB)-penetrable compounds and are considered as proficient central nervous system active and neuroprotective antioxidant agents as the neuroprotective property is determined with BBB penetration thresholds.

Synthesis of novel rapanone derivatives via organocatalytic reductive C-alkylation: biological evaluation of antioxidant properties, in vivo zebrafish embryo toxicity, and docking studies

“…This is the first-time investigation of the antioxidant properties of the derivatives evaluated using DPPH and ABTS. 23 All of the C-alkylated compounds were evaluated at six different concentrations (5,10,20,40,80, and 160 μM), as given in the ESI † (Fig. S66 and S67).…”

“…The earlier DPPH and ABTS antioxidant assay results indicated excellent radical scavenging activities of rapanone derivatives with electron-donating groups ( 5a–5i , 5v , 5w , 5zc , and 5zd ). Hence, these compounds were tested for their binding potentialities against selected enzymatic protein chains 20 along with the standard antioxidant l -Aa . This study performed molecular docking for the compounds ( 1 , 5a–5i , 5v–5w , 5zc , 5zd , and l -Aa ) against the target protein receptor in PDB: protein.…”

“…The structure of semi-synthesized reductive C-alkylated rapanone derivatives was confirmed by standard spectroscopic characterization methods. Antioxidant (DPPH) and (ABTS) free radical scavenging activities, as well as in vivo toxicity assessment using zebrafish embryos, were also evaluated 20 for the semi-synthesized C-alkylated derivatives. Additionally, molecular docking studies were performed to understand the role of newly introduced substituent groups in altering the bioactivity of the parent compound ( 5a–5ze ).…”

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

“…Silica-gel-supported iodine was used as the catalyst under solvent-free conditions. The plant growth regulatory activity of the products was investigated ( Scheme 39 ) [ 62 ].…”

One-pot synthesis of α-aminophosphonates by yttrium-catalyzed Birum–Oleksyszyn reaction

“…These organophosphorus compounds have attracted the attention of medicinal chemists due to their similarity to α-amino acids. They find application in agriculture as plant growth regulators 1 and herbicides, 2 in medicinal chemistry as antibacterial, 3,4 antiviral 5 and antitumor agents, 6 activity-based probes, 7 and building blocks for peptides and proteins. 8 Since the first preparation of α-aminophosphonates, reported in 1952 by Fields, 9 various methods for their synthesis have been proposed.…”