Bismuth(III) Chloride Mediated Michaelis–Arbuzov Reaction: A Facile Synthesis of Substituted Arylphosphonates/Phosphinates and Bioactivity Evaluation

Subramanyam, Ch.; Golla, Madhava; Basha, Sakeenabi; Rasheed, Syed Basit; Sankar, A. U. R.; Raju, C. Naga

doi:10.1080/10426507.2015.1043048

Cited by 9 publications

(5 citation statements)

References 32 publications

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“…S1A). The addition of a Lewis acid catalyst (15)(16)(17) enables the Arbuzov reaction to be applied universally to GO to provide PGs with a controlled density of polyphosphate anchor points and a plethora of counterions. This key addition of magnesium bromide diethyl etherate as a catalyst to activate the epoxides on GO enhances efficiency and enables this functionalization method to serve in biomedical applications: control of the polyphosphate density and incorporation of a wide range of counterions were not previously accessible (18) (SI Appendix, Fig.…”

Section: Resultsmentioning

confidence: 99%

Phosphate graphene as an intrinsically osteoinductive scaffold for stem cell-driven bone regeneration

Arnold

Holt

Daneshmandi

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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Synthetic, resorbable scaffolds for bone regeneration have potential to transform the clinical standard of care. Here, we demonstrate that functional graphenic materials (FGMs) could serve as an osteoinductive scaffold: recruiting native cells to the site of injury and promoting differentiation into bone cells. By invoking a Lewis acid-catalyzed Arbuzov reaction, we are able to functionalize graphene oxide (GO) to produce phosphate graphenes (PGs) with unprecedented control of functional group density, mechanical properties, and counterion identity. In aqueous environments, PGs release inducerons, including Ca2+ and PO43−. Calcium phosphate graphene (CaPG) intrinsically induces osteogenesis in vitro and in the presence of bone marrow stromal cells (BMSCs), can induce ectopic bone formation in vivo. Additionally, an FGM can be made by noncovalently loading GO with the growth factor recombinant human bone morphogenetic protein 2 (rhBMP-2), producing a scaffold that induces ectopic bone formation with or without BMSCs. The FGMs reported here are intrinsically inductive scaffolds with significant potential to revolutionize the regeneration of bone.

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Section: Resultsmentioning

confidence: 99%

Phosphate graphene as an intrinsically osteoinductive scaffold for stem cell-driven bone regeneration

Arnold

Holt

Daneshmandi

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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“…Organophosphorus compounds, in particular phosphinic acids (R 1 R 2 P(=O)OH), are known to have antibacterial properties . Phosphinic acids, like sulfonic acids, have low pKa values, generate ligands which complex through their O atoms, and would be expected to generate similarly labile complexes.…”

Section: Introductionmentioning

confidence: 99%

“…[49][50][51][52] Organophosphorus compounds, in particularp hosphinic acids (R 1 R 2 P(=O)OH), are known to have antibacterialp roperties. [53][54][55] Phosphinic acids, like sulfonic acids, have low pKa values, generatel igandsw hich complex throught heir O atoms, and would be expected to generate similarly labile complexes.W hile there have been several reports on organophosphinato bismuth compounds in the literature, [56][57][58] there have been no reports exploring their biological activity.S ince the antibacterial activity of bismuth(III) complexes are known to be profoundly ligand dependent, [59] there is significant potential in exploring the synergistic effects of Bi III and phosphinato ligands towards multi-drug resistant bacteria, with ah ope that the activity would be similar to, if not better than, analogous sulfonato complexes.…”

Section: Introductionmentioning

confidence: 99%

Bismuth Phosphinates in Bi‐Nanocellulose Composites and their Efficacy towards Multi‐Drug Resistant Bacteria

Werrett

Herdman

Brammananth

et al. 2018

Chemistry A European J

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A series of poorly soluble phenyl bis-phosphinato bismuth(III) complexes [BiPh(OP(=O)R R ) ] (R =R =Ph; R =R =p-OMePh; R =R =m-NO Ph; R =Ph, R =H; R =R =Me) have been synthesised and characterised, and shown to have effective antibacterial activity against Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE). The bismuth complexes were incorporated into microfibrillated (nano-) cellulose generating a bismuth-cellulose composite as paper sheets. Antibacterial evaluation indicates that the Bi-cellulose materials have analogous or greater activity against Gram positive bacteria when compared with commercial silver based additives: silver sulfadiazine loaded at 0.43 wt % into nanocellulose produces a 10 mm zone of inhibition on the surface of agar plates containing S. aureus whereas [BiPh(OP(=O)Ph ) ] loaded at 0.34 wt % produces an 18 mm zone of inhibition. These phenyl bis-phosphinato bismuth(III) complexes show potential to be applied in materials in healthcare facilities, to inhibit the growth of bacteria capable of causing serious disease.

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“…In this modification of the MA reaction, it should be noted that the aryl bromines are unreactive [ 38 ]. Aryl phosphonates/phosphinates have also been formed at the low temperature of 40 °C using BiCl 3 as the Lewis acid catalyst under nitrogen atmosphere [ 39 ]. Other Lewis catalysts include the Pd 2 (dba) 3 in the presence of PhOTf and in a solvent free environment for triaryl phosphite intramolecular rearrangement [ 40 ], the CeCl 3 .7H 2 O-SiO 2 [ 41 ], the CeCl 3 .7H 2 O [ 42 ], the already-mentioned ZnBr 2 [ 19 , 20 ], the NiCl 2 [ 43 ] that also allows the usage of aryltriflates as reactants [ 44 ], the InBr 3 [ 20 ], the InCl 3 that allows the reaction of N-benzyloxycarbonylaminosulfones with triethyl phosphite to generate α-amino phosphonates [ 45 ], and the NbCl 5 [ 46 ].…”

Section: Improvements In and Variations Of The Ma Reactionmentioning

confidence: 99%

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

Kostoudi

Pampalakis

2022

IJMS

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Compounds bearing the phosphorus–carbon (P–C) bond have important pharmacological, biochemical, and toxicological properties. Historically, the most notable reaction for the formation of the P–C bond is the Michaelis–Arbuzov reaction, first described in 1898. The classical Michaelis–Arbuzov reaction entails a reaction between an alkyl halide and a trialkyl phosphite to yield a dialkylalkylphosphonate. Nonetheless, deviations from the classical mechanisms and new modifications have appeared that allowed the expansion of the library of reactants and consequently the chemical space of the yielded products. These involve the use of Lewis acid catalysts, green methods, ultrasound, microwave, photochemically-assisted reactions, aryne-based reactions, etc. Here, a detailed presentation of the Michaelis–Arbuzov reaction and its developments and applications in the synthesis of biomedically important agents is provided. Certain examples of such applications include the development of alkylphosphonofluoridates as serine hydrolase inhibitors and activity-based probes, and the P–C containing antiviral and anticancer agents.

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Bismuth(III) Chloride Mediated Michaelis–Arbuzov Reaction: A Facile Synthesis of Substituted Arylphosphonates/Phosphinates and Bioactivity Evaluation

Cited by 9 publications

References 32 publications

Phosphate graphene as an intrinsically osteoinductive scaffold for stem cell-driven bone regeneration

Phosphate graphene as an intrinsically osteoinductive scaffold for stem cell-driven bone regeneration

Bismuth Phosphinates in Bi‐Nanocellulose Composites and their Efficacy towards Multi‐Drug Resistant Bacteria

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

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