The phospha-Michael addition of dimethyl- and diphenylphosphites to the η1-N-maleimidato ligand: Inhibition of serine hydrolases by half-sandwich metallocarbonyl azaphosphonates

Rudolf, Bogna; Salmain, Michèle; Palusiak, Marcin; Zakrzewski, Janusz

doi:10.1016/j.jorganchem.2008.10.057

Cited by 13 publications

(12 citation statements)

References 39 publications

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“…Later in 2009, Rudolf et al. described the addition of dialkyl phosphites to the η 1 ‐ N ‐maleimidato ligand 191 , resulting in the formation of phosphonates bearing metallocarbonyl moieties 192 (Scheme ) …”

Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

“…Aminobisphosphonates have the ability to inhibit farnesyl diphosphate synthase, a key enzyme in the mevalonate pathway, and to affect cellular activity and cell survival . γ‐Ketophosphonic acid derivatives 7 with a succinic acid motif have shown significant inhibition of the serine hydrolases of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) . Six‐ or seven‐membered phosphorylated nitrogen heterocycles bearing a C( sp 3 )−P bond such as 8 – 10 are potential anticancer, antimicrobial agents and good clostripain inhibitors .…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

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“…[7] The phospha-Michael addition of dimethyl-or diphenyl-phosphite to maleimide 2 was carried out in the presence of DBU to afford the ferrocenyl phosphonates 3a-b (Scheme 1).…”

Section: Synthesismentioning

confidence: 99%

“…[14] Recently we found out that the metallocarbonyl phosphonate 1b acted as a competitive inhibitor of BChE and was also able to inactivate both BChE and α-chymotrypsin in a time-dependent fashion. [7] Thus, we thought it was interesting to investigate whether the ferrocenyl phosphonate diester complexes 3a-b were also able to inhibit the cholinesterases AChE and BChE and what was their mechanism of inhibition.…”

Section: Biochemical Assaysmentioning

confidence: 99%

“…1) derived from (η 5 -C 5 H 5 )Fe(CO) 2 (η 1 -N-maleimidato). [7] Organophosphorus compounds are able to inhibit serine hydrolases by phosphorylation of the active site serine residue. For example, the diphenyl phosphonate 1b was shown to inhibit the serine hydrolase butyrylcholinesterase (BChE) in a reversible manner according to a competitive mechanism and inactivated this enzyme in a time-dependent fashion by phosphonylation of its active site serine residue.…”

Section: Introductionmentioning

confidence: 99%

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Novel ferrocenyl phosphonate derivatives. Inhibition of serine hydrolases by ferrocene azaphosphonates

Rudolf

Salmain

Haquette

et al. 2010

Applied Organom Chemis

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Owing to their unique properties, ferrocene compounds are gaining increasing interest for biological applications, particularly as enzyme inhibitors. Phosphonate derivatives including a ferrocenyl moiety were synthesized by reaction of dimethyl-and diphenylphosphite with ferrocenyl methyl maleimide. The ferrocenyl diphenyl phosphonate complex was characterized by X-ray diffraction. The ability of these organometallic compounds to inhibit the enzymatic activity of the serine esterases acetyland butyrylcholinesterase was investigated. It appeared that the new ferrocenyl phosphonates inhibited both enzymes by competitive, mixed or non competitve mechanisms with inhibition constants in the range 35-1000 µM. Both compounds also behave as slow time-dependent inactivators of butyrylcholinesterase. The presence of the ferrocenyl entity seems then to have a dramatic effect on the biochemical behavior of the systems.

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Michael addition

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2020

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The phospha-Michael addition of dimethyl- and diphenylphosphites to the η1-N-maleimidato ligand: Inhibition of serine hydrolases by half-sandwich metallocarbonyl azaphosphonates

Cited by 13 publications

References 39 publications

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Novel ferrocenyl phosphonate derivatives. Inhibition of serine hydrolases by ferrocene azaphosphonates

Michael addition

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