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Synthesis and Biological Applications of Phosphinates and Derivatives

  • David VirieuxEmail author
  • Jean-Noël Volle
  • Norbert Bakalara
  • Jean-Luc PiratEmail author
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 360)

Abstract

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.

Keywords

Bioisostere Phosphinate Phosphinic acid Tetrahedral transition state 

Abbreviations

ABCN

1,1′-Azobis(cyclohexanecarbonitrile)

acac

Acetylacetonate

Ac

Acetyl

ADP

Adenosine diphosphate

AIBN

2,2′-Azobisisobutyronitrile

anhyd

Anhydrous

Ar

Aryl

ATP

Adenosine triphosphate

AZT

Azidothymidine

BHMT

Betaine-homocysteine methyltransferase

Bn

Benzyl

Boc

tert-Butoxycarbonyl

BP

Bis(phosphonate)

BSA

N,O-(Bistrimethylsilyl)acetamide

Bu

Butyl

Bz

Benzoyl

Cbz

Benzyloxycarbonyl

CNS

Central nervous system

d

Day(s)

DABCO

1,4-Diazabicyclo[2.2.2]octane

DAST

Diethylaminosulfur trifluoride

DBU

1,8-Diazabicyclo [5.4.0]undec-7-ene

DCC

N,N-Dicyclohexylcarbodiimide

DEAD

Diethyl azodicarboxylate

DIAD

Diisopropyl azodicarboxylate

DIEPA

Diisopropylethylamine

DMAP

4-(Dimethylamino)pyridine

DMF

Dimethylformamide

DMSO

Dimethyl sulfoxide

DOTA

1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid

dppp

Diphenylphosphinopropane

EC50

Half maximal effective concentration

EDC

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

Et

Ethyl

FDA

Food and drug administration

Fmoc

9-Fluorenylmethoxycarbonyl

GABA

γ-Aminobutyric acid

GPCRs

G-Protein-coupled-receptors

GR

Glutamate racemase

h

Hour(s)

HATU

1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]-pyridinium 3-oxid hexafluorophosphate

HBTU

N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate

HCV

Hepatitis C virus

HIV

Human Immunodeficiency Virus

HMDS

Hexamethyldisilazane

HMPA

Hexamethylphosphoric triamide

HOBt

Hydroxybenzotriazole

i-Pr

Isopropyl

LDA

Lithium diisopropylamide

LogP

Partition-coefficient

LTMP

Lithium 2,2,6,6-tetramethylpiperidide

m-CPBA

m-Chloroperoxybenzoic acid

MDCK

Madin-Darby canine kidney

Me

Methyl

mGluR

Metabotropic glutamate receptors

MIC

Minimum inhibitory concentration

mol

Mole(s)

NA

Neuraminidase

NBS

N-Bromosuccinimide

NNM

N-Methyl morpholine

NNRTI

Non-nucleoside reverse transcriptase inhibitor

Np

Naphthyl

NRTI

Nucleoside reverse transcriptase inhibitor

PALA

N-Phosphonoacetyl-l-aspartate

Ph

Phenyl

Pr

Propyl

PTM

Post-translational modification

rt

Room temperature

RT

Reverse transcriptase

s-Bu

sec-butyl

TBDMS

tert-Butyldimethylsilyl

t-Bu

tert-Butyl

TEBAC

Triethylbenzylammonium chloride

THF

Tetrahydrofuran

TLESR

Transient lower oesophageal sphincter relaxation

TMG

Tetramethylguanidine

TMS

Trimethylsilyl

TMS-N3

Trimethylsilyl azide

TS

Transition state

UTP

Uridine 5′-triphosphate

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Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  1. 1.UMR 5253 - ICG Montpellier, Equipe AM2N, ENSCMMontpellier Cedex 5France
  2. 2.INSERM U-1051. Institut des neurosciences de MontpellierMontpellierFrance

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