Synthesis of phosphinic analogs of sulfur-containing amino acids

Zhukov, Yu. N.; Khomutov, Alex R.; Osipova, T. I.; Khomutov, R. M.

doi:10.1007/bf02495302

Cited by 11 publications

(6 citation statements)

References 6 publications

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“…Each structure was obtained in 56-64% yield, by mixing ethyl 5-bromovalerate or ethyl 5-bromo-3,3-dimethylpentanoate with phosphinomethionine 238 in the presence of sodium and ammonia (Scheme 46). The H-phosphinic acid intermediate 238 was readily accessible by a sequence of three steps from acrolein [162][163][164].…”

Section: Inhibitors Of Betaine-homocysteine Methyltransferasementioning

confidence: 99%

Synthesis and Biological Applications of Phosphinates and Derivatives

Virieux

Volle

Bakalara

et al. 2014

Topics in Current Chemistry

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This review first outlines general considerations on phosphinic acids and derivatives as bioisosteric groups. The next sections present key aspects of phosphinic acid-based molecules and include a brief description of the biological pathways involved for their activities. The synthetic aspects and the biological activities of such compounds reported in the literature between 2008 and 2013 are also described.

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Section: Inhibitors Of Betaine-homocysteine Methyltransferasementioning

confidence: 99%

Synthesis and Biological Applications of Phosphinates and Derivatives

Virieux

Volle

Bakalara

et al. 2014

Topics in Current Chemistry

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“…HgCl 2 , despite its toxicity and environmental hazard is nevertheless an efficient reagent for the oxidation of phosphinic acid [ 244 ]. Diiodide in the presence of acid (HI) in water/ethanol solution yields the oxidation of the phosphinic acid 130 without oxidizing the thioether function [ 245 ] ( Fig. 36 ).…”

Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

149

103

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The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P–C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

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“…The reaction mixture was heated to reflux for 4 h and then concentrated in vacuo. 18,19 The residue was dissolved in aqueous HCl (3 M, 200 mL) and washed with diethyl ether (3 × 100 mL). The pH was adjusted to 1.5 by addition of solid Na 2 CO 3 .…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…For the synthesis of 12 , commercially available 2-aminoethanol was Fmoc-protected followed by oxidation with IBX. , The corresponding aldehyde 8 was converted with hydroxylamine hydrochloride in DCM to oxime 9 in high yield . Refluxing oxime 9 with anhydrous crystalline phosphinic acid in dry methanol resulted in racemic phosphinate intermediate 10 , , which was sulfonylated upon treatment with phenylsulfonyl chloride in aqueous Na 2 CO 3 to provide Fmoc-protected derivative 11 . Fmoc deprotection and purification by reverse-phase high-performance liquid chromatography (RP-HPLC) afforded fragment 12 as a racemic mixture.…”

Section: Chemistrymentioning

confidence: 99%

Tailoring of Integrin Ligands: Probing the Charge Capability of the Metal Ion-Dependent Adhesion Site

et al. 2012

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Intervention in integrin-mediated cell adhesion and integrin signaling pathways is an ongoing area of research in medicinal chemistry and drug development. One key element in integrin-ligand interaction is the coordination of the bivalent cation at the metal ion-dependent adhesion site (MIDAS) by a carboxylic acid function, a consistent feature of all integrin ligands. With the exception of the recently discovered hydroxamic acids, all bioisosteric attempts to replace the carboxylic acid of integrin ligands failed. We report that phosphinates as well as monomethyl phosphonates represent excellent isosters, when introduced into integrin antagonists for the platelet integrin αIIbβ3. The novel inhibitors exhibit in vitro and ex vivo activities in the low nanomolar range. Steric and charge requirements of the MIDAS region were unraveled, thus paving the way for an in silico prediction of ligand activity and in turn the rational design of the next generation of integrin antagonists.

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Synthesis of phosphinic analogs of sulfur-containing amino acids

Cited by 11 publications

References 6 publications

Synthesis and Biological Applications of Phosphinates and Derivatives

Synthesis and Biological Applications of Phosphinates and Derivatives

Phosphonic acid: preparation and applications

Tailoring of Integrin Ligands: Probing the Charge Capability of the Metal Ion-Dependent Adhesion Site

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