Phosphorus based inhibitors of matrix metalloproteinases

Veerendhar, Ainelly; Reich, Reuven; Breuer, Eli

doi:10.1016/j.crci.2010.07.003

Cited by 19 publications

(13 citation statements)

References 91 publications

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“…This constitutes a considerable obstacle to progress at present, given the bioavailability profiles of N-BP's observed in non-calcified tissues [121]. In these areas, 3-D QSAR analytical methods have been instrumental in identifying the molecular sites of action of dronates, and in describing desirable pharmacophore arrangements for drug development.…”

Section: Discussionmentioning

confidence: 99%

N-Heterocyclic Dronic Acids: Applications and Synthesis

Hudson

Wardle

Bligh

et al. 2012

MRMC

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Substituted hydroxymethylenebisphosphonic acid derivatives--either as dronic acids or their dronate sodium salts, are important pharmaceuticals in the treatment of diseases arising from excessive bone-resorption. Potential has also been identified in areas ranging from parasite-growth inhibition to immunological and cancer therapeutics. Representative clinically relevant N-heterocyclic derivatives include zoledronic and risedronic acids. The biochemical background and mechanism of action of these drugs are discussed, along with trends in structural development and future prospects. Synthetic routes to dronates are then summarized. The most popular route to valuable dronic acids involves the 3- component condensation of a substituted acetic acid, phosphorous acid, and phosphorus trichloride. However, the protocols recorded in the literature are very diverse. This review gives a critical account of reported methods, explores the contradictions and suggests a practical synthetic procedure after clarifying the inconsistencies described. Possible mechanisms of the reaction are also discussed.

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Section: Discussionmentioning

confidence: 99%

N-Heterocyclic Dronic Acids: Applications and Synthesis

Hudson

Wardle

Bligh

et al. 2012

MRMC

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“…Àêòèâíîñòü è ñåëåêòèâíîñòü äëÿ ñîåäèíåíèÿ (XVIIIá) ïî÷òè â 10 ðàç âûøå, ÷åì äëÿ ñîåäèíåíèÿ (XVIIIà). Ñîåäèíåíèå (XIX) àêòèâíî ïî îòíîøåíèþ ê MMP-2 (IC 50 = 60 íÌ) è ñåëåêòèâíî ê ÌÌÏ-3, ÌÌÏ-8, ÌÌÏ-9, ÌÌÏ-13 è ÌÌÏ-14 [27].…”

Section: ôîñôîíîâûå êèñëîòûunclassified

Основные Структурные Типы Ингибиторов Матриксных Металлопротеиназ

2017

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В обзоре рассмотрены основные структурные типы ингибиторов матриксных металлопротеиназ (ММП) — производные гидроксамовой кислоты, сульфонамиды, бисфосфонаты, соединения, сочетающие фосфорильную и гидроксаматную группы, функционализированные производные фосфоновых и фосфиновых кислот. Обсуждается селективность их ингибирующего действия в отношении отдельных типов ММП и перспективы практического использования в терапии раковых заболеваний.

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“…[5] Of the many published inhibitors of DXR, a large majority contain the hydroxamic acid functionality which is already present in fosmidomycin, resulting in less effort toward other classes of inhibitors. [5] Of the many published inhibitors of DXR, a large majority contain the hydroxamic acid functionality which is already present in fosmidomycin, resulting in less effort toward other classes of inhibitors.…”

Section: Introductionmentioning

confidence: 99%

“…[4] Phosphinic acids are often employed as complexing units particularly in the inhibition of matrix metalloproteinases (MMPs), a family of zinc-dependent endoproteinases. [5] Of the many published inhibitors of DXR, a large majority contain the hydroxamic acid functionality which is already present in fosmidomycin, resulting in less effort toward other classes of inhibitors. From a structural point of view, the tetrahedral geometry of the phosphinic acid group could directly mimic the tetrahedral alcohol function of DXP (2).…”

Section: Introductionmentioning

confidence: 99%

Functionalized Phosphanyl‐Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin

et al. 2012

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International audienceFosmidomycin (1a) and FR-90098 are potent inhibitors of 1- deoxy-D-xylulose-5-phosphate reductoisomerase (DXR), the second enzyme of the non-mevalonate (MEP) pathway responsible for the biosynthesis of isoprenoids. This paper describes the synthesis of four types of targets bearing a phosphanyl-phosphonic acid motif as the common core for the inhibition of DXR. In these structures, the hydroxamic acid was replaced by various chelators based on a phosphinic acid linked to different functional groups capable of forming fiveor six-membered chelating rings

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Phosphorus based inhibitors of matrix metalloproteinases

Cited by 19 publications

References 91 publications

N-Heterocyclic Dronic Acids: Applications and Synthesis

N-Heterocyclic Dronic Acids: Applications and Synthesis

Основные Структурные Типы Ингибиторов Матриксных Металлопротеиназ

Functionalized Phosphanyl‐Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin

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