Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′−2′-2-(2′-phosphonocyclopropyl)glycines

Marinozzi, Maura; Serpi, Michaela; Amori, Laura; Diaz, Monica Gavilan; Costantino, Gabriele; Meyer, Udo; Flor, Peter J.; Gasparini, F.; Heckendorn, Roland; Kühn, Rainer; Giorgi, Gianluca; Hermit, Mette Brunsgaard; Thomsen, C.; Pellicciari, Roberto

doi:10.1016/j.bmc.2007.02.040

Cited by 14 publications

(5 citation statements)

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“…27 ). Similar acidic hydrolysis was used to produce the imidazolyl phosphonic acid 91 [ 214 ], 92 [ 215 ], the chiral phosphonic-carboxylic acid 93 [ 216 ] or the cyclopropylphosphonic acid 94 that was assessed as inhibitor of the glutamate metabotropic receptors [ 217 ].…”

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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Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

149

103

View full text Add to dashboard Cite

show abstract

“…The synthesis of an mGluR agonist was achieved using chloromethyl phosphonamide 28d [60–61], as discussed later in this review.…”

Section: Reviewmentioning

confidence: 99%

“…9) [124]. To this end, phosphonocyclopropylamino acid 21 was designed as an analogue to 163 by replacing a carboxylic acid with a phosphonic acid moiety [60–61]. The stereoselective synthesis of 21 relied on another cyclopropanation protocol developed by Hanessian and co-workers [59].…”

Section: Reviewmentioning

confidence: 99%

“…Oxidative cleavage with Pb(OAc) 4 liberated the amino functionality and hydrolysis of both the phosphonamide and nitrile groups under acidic conditions finally provided phosphonocyclopropylamino acid 21 . This compound showed to be a group III mGluRs selective ligand with moderate potency as mGluR4 and mGluR6 agonist (EC 50 59 µM and 51 µM, respectively) [60–61 124]. …”

Section: Reviewmentioning

confidence: 99%

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Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

Focken¹,

Hanessian²

2014

Beilstein J. Org. Chem.

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SummaryA review of the synthesis of natural products and bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be summarized, as well as an overview of the synthesis of the employed phosphonamide reagents.

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“…The phosphonate moiety is the most common functionality present in known PCDCs. Thus, these PCDCs have been extensively used for the preparation of different classes of biologically active phosphonic acid derivatives, often employed in medicinal chemistry due to their increased stability to enzymatic hydrolysis when compared to their corresponding phosphate analogues. , As an example, α-amino phosphonic acid derivatives are key building blocks in the synthesis of phosphonopeptides, which can act as enzyme inhibitors, antibiotics, plant regulators, and haptens of catalytic antibodies. − In the literature, the ability of the phosphonic acid moiety to function as bioisosteric replacement not only for the phosphate, ,− but also for sulfate and carboxylate groups, − is well documented. Furthermore, the ability of phosphorus moiety to specifically coordinate with metal-dependent enzymes explains the presence of a lot of phosphorus-functionalized molecules among enzyme inhibitors. − The use of phosphonic acids in coordination chemistry has been recently reviewed .…”

Section: Introductionmentioning

confidence: 99%

λ⁵-Phosphorus-Containing α-Diazo Compounds: A Valuable Tool for Accessing Phosphorus-Functionalized Molecules

2016

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The compounds characterized by the presence of a λ-phosphorus functionality at the α-position with respect to the diazo moiety, here referred to as λ-phosphorus-containing α-diazo compounds (PCDCs), represent a vast class of extremely versatile reagents in organic chemistry and are particularly useful in the preparation of phosphonate- and phosphinoxide-functionalized molecules. Indeed, thanks to the high reactivity of the diazo moiety, PCDCs can be induced to undergo a wide variety of chemical transformations. Among them are carbon-hydrogen, as well as heteroatom-hydrogen insertion reactions, cyclopropanation, ylide formation, Wolff rearrangement, and cycloaddition reactions. PCDCs can be easily prepared from readily accessible precursors by a variety of different methods, such as diazotization, Bamford-Stevens-type elimination, and diazo transfer reactions. This evidence along with their relative stability and manageability make them appealing tools in organic synthesis. This Review aims to demonstrate the ongoing utility of PCDCs in the modern preparation of different classes of phosphorus-containing compounds, phosphonates, in particular. Furthermore, to address the lack of precedent collective papers, this Review also summarizes the methods for PCDCs preparation.

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Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′−2′-2-(2′-phosphonocyclopropyl)glycines

Cited by 14 publications

References 23 publications

Phosphonic acid: preparation and applications

Phosphonic acid: preparation and applications

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

λ⁵-Phosphorus-Containing α-Diazo Compounds: A Valuable Tool for Accessing Phosphorus-Functionalized Molecules

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Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′−2′-2-(2′-phosphonocyclopropyl)glycines

Cited by 14 publications

References 23 publications

Phosphonic acid: preparation and applications

Phosphonic acid: preparation and applications

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

λ5-Phosphorus-Containing α-Diazo Compounds: A Valuable Tool for Accessing Phosphorus-Functionalized Molecules

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λ⁵-Phosphorus-Containing α-Diazo Compounds: A Valuable Tool for Accessing Phosphorus-Functionalized Molecules