Aminophosphonic and Aminophosphinic Acids Chemistry and Biological Activity

by Kukhar, Valery P.; Hudson, Harry R.

Edition: 1st

ISBN13: 9780471891499

ISBN10: 0471891495

Format: Hardcover

Pub. Date: 2000-06-08

Publisher(s): WILEY

Other versions by this Author

This Item Qualifies for Free Shipping!*

*Excludes marketplace orders.

List Price: ~~$1,016.88~~

Buy New

Arriving Soon. Will ship when available.

$968.46

Add to Cart

Rent Textbook

Select for Price

Add to Cart

There was a problem. Please try again later.

Used Textbook

We're Sorry
Sold Out

eTextbook

We're Sorry
Not Available

Summary

Aminophosphinic and aminoposphonic acids, synthetic analogs to natural amino acids, have attained a position of prominence in research--particularly in research involving the modification of physiological processes in living organisms.Aminophosphonic and Aminophosphinic Acids provides a comprehensive insight into the chemistry and biological activity of these compounds. Separate chapters are devoted to naturally-occurring derivatives, synthetic procedures, structural, spectroscopic and analytical aspects, metal complexes, agrochemicals, neuroactive compounds and biomedical applications and transition-state analogue enzyme inhibitors, with particular emphasis on inhibitors of HIV protease, thrombin and human collagenase. This book is a valuable source of information for researchers working with these types of compounds in biomedical and agrochemical industries and all others working with synthetic analogues of biologically important molecules.

Author Biography

Valery P. Kukhar is the author of Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, published by Wiley. Harry R. Hudson is the author of Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, published by Wiley.

Contributors

xvii

Preface

xxiii

Naturally Occurring Aminophosphonic and Aminophosphinic Acids

(32)

Przemyslaw Mastalerz

Pawel Kafarski

2-Aminoethanephosphonic acid (AEP, ciliatane)

(6)

Phosphonates metabolically related to 2-aminoethanephosphonic acid

(1)

Aminophosphonate antibiotics and related compounds

(1)

Antibiotic phosphonopeptides

(5)

Biosynthesis of the P--C bond

(2)

Biosynthesis of 2-aminoethanephosphonic acid and its N-methylated derivatives

(1)

Biosynthesis of bialaphos

(1)

Biodegradation of organophosphonates

(4)

The origin of aminophosphonates in nature

(1)

References

(10)

Synthesis of α-Aminoalkanephosphonic and α-Aminoalkanephosphinic Acids

(42)

Pawel Kafarski

Jerzy Zon

Aldehydes and ketones as substrates for the preparation of aminophosphonates

(16)

Amidolkylation of trivalent phosphorus compounds

(3)

Mannich-type condensation of amines with aldehydes and phosphorous or hypophosphorous acid

(1)

Kabachnik-Fields reaction

(3)

Hydrophosphonylation of imines

(3)

Hydrophosphonylation of other C=N bonds

(2)

Hydrophosphonylation of triazines

(1)

Hydrophosphonylation of aldehydes-hydroxyalkanephosphonates as substrates for the preparation of 1-aminoalkanephosphonates

(3)

Carboxylic acids as substrates for the synthesis of 1-aminoalkanephosphonic acids

(5)

1-Oxoalkanephosphonates as substrates

(3)

Phosphonoacetates as substrates

(1)

Replacement of amino acid carboxylic moieties by phosphonic groups

(1)

Nitriles as substrates

(1)

Phosphonylation of halogenoalkylamines and related compounds

(3)

Amination of alkanephosphonates and functionalized alkanephosphonates

(2)

Nucleophilic amination

(1)

Electrophilic amination

(1)

Alkylation of derivatives of dialkyl aminomethanephosphonates

(3)

Alkylation of Schiff bases

(1)

Alkylation of other derivatives of aminomethanephosphonic acid

(2)

Hydrogenation of N-acyl-α, β-dehydroaminophosphonates

(1)

Other methods

(3)

Hydrolytic cleavage of carbon-phosphorus bond

(1)

References

(8)

Synthesis of Aminoalkanephosphonic and Aminoalkanephosphinic Acids with the Amino Substituent in other than the α-Position

(28)

Valery P. Kukhar

Synthesis of ω-aminophosphonates by addition of amines to unsaturated phosphonates

(2)

Introduction of the amino function by ketophosphonate transformation

(4)

Formation of the amino function in phosphonates by reduction of nitrogen-containing groups

(1)

Syntheses of aminophosphonates by the Arbuzov and Michaelis--Becker reactions

(2)

Synthesis of aminoalkanephosphonic acids by Curtius and Hofmann rearrangements

(1)

Syntheses of aminophosphonates by the carbanion approach

(2)

Miscellaneous reactions leading to aminophosphonates

(4)

Arenephosphonic acids containing an amino function in the ring

(2)

Nitrogen heterocycles with a phosphonic (or phosphinic) acid residue

(5)

References

(4)

α-Amino Acid Analogues Bearing Side-Chain C-P Linkages

103

(24)

Sharon Lall

Robert Engel

Introduction

103

(1)

Syntheses and biological significance

104

(1)

Analogues of biological α-amino acids

104

(11)

Structures of interest

104

(2)

Syntheses of analogues of phosphinothricin

106

(3)

Other potentially useful analogues of phosphinothricin

109

(1)

Analogues of glutamic and aspartic acid--structure

110

(1)

Analogues of glutamic and aspartic acid--syntheses and biology

110

(5)

Analogues of amino acid phosphate esters

115

(4)

Biology and structure

115

(1)

Analogues of amino acid phosphate esters--synthesis

116

(3)

Other α-amino acids containing a C-P bond in the side-chain

119

(1)

Analogues of phosphatidylserine

120

(1)

Consideration for future studies

121

(1)

References

122

(5)

Asymmetric Synthesis of Aminophosphonic and Aminophosphinic Acids

127

(46)

Valery P. Kukhar

Enantioselective C--C Bond forming reactions

128

(15)

Chiral `glycine' synthons--chirality in the nitrogen residue

128

(9)

Chiral `glycine' synthons--chirality in the phosphorus residue

137

(2)

Catalyzed C--C bond formation reaction leading to chiral aminophosphonates

139

(1)

Miscellaneous C--C bond formation reactions leading to chiral aminophosphonates

140

(3)

Enantioselective C--P bond forming reactions

143

(11)

Addition of hydrophosphonyl compounds to imines

143

(5)

Three-component Kabachnik--Fields reaction

148

(3)

Catalytic addition of hydrophosphonyl compounds to C=N bonds

151

(1)

Miscellaneous reactions for stereoselective C--P bond formation

152

(2)

Stereoselective C--N bond formation

154

(10)

Steroselective C--H bond forming reactions

164

(3)

Conclusions

167

(1)

References

168

(5)

Synthesis of Phosphono-and Phosphinopeptides

173

(32)

Pawel Kafarski

Barbara Lejcczak

Protection of the amino group

174

(2)

Protection of the phosphonic moiety

176

(2)

Synthesis of phosphono-and phosphinopeptides containing P-terminal aminophosphonate

178

(5)

Preparation of diastereomeric phosphonodipeptides containing P-terminal aminophosphonate

183

(1)

Phosphonodepsipeptides containing P-terminal hydroxyphosphonate

183

(1)

Peptides containing a phosphonic or phosphinic moiety in the side-chain

184

(3)

Peptides containing a phosphonamide or phosphinamide bond

187

(4)

Phosphonodepsipeptides containing a phosphonoester moiety

191

(2)

Phosphinopeptide nucleic acids

193

(1)

Phosphinopeptides in which a phosphinic acid replaces a dipeptidyl fragment of the peptide chain

194

(2)

Peptides in which a PH2 group replaces the NH2 moiety

196

(1)

References

196

(9)

Column Chromatography of Aminophosphonic Acids and Phosphonopeptides

205

(12)

S. V. Galushko

Introduction

205

(1)

Separation of phosphonopeptides using column liquid chromatography

206

(1)

Chiral recognition of aminophosphonic acids

207

(6)

Derivatization of aminophosphonic acids for HPLC analysis

213

(1)

Derivatization of aminophosphonic acids for gas chromatographic analysis

214

(1)

Optimization and problem solving

215

(1)

References

215

(2)

Physical Properties and NMR-Spectroscopic Characterization of Aminophosphonates and Aminophosphinates

217

(68)

Gerhard Hagele

Introduction

217

(2)

The 1H-NMR spectrum of α-N-phenylamino-α-phenylmethanephosphonic acid diethyl ester

219

(14)

The aromatic region

219

(3)

The-CHP-NH-skeleton

222

(1)

The alkoxy region

223

(3)

Aromatic ring current effects and molecular structure

226

(7)

1H-, 19F-and 31 P-NMR spectra of aromatic substitutents Ar1 and Ar2 and related fragments in α-N-arylamino-α-arylmethanephosphonic acid diethyl esters

233

(1)

Increasing complexity by sterically demanding aromatic substituents in Ar1 or Ar2

234

(8)

The 1-naphthyl group attached to the CHP unit

234

(3)

The 2-naphthyl group attached to the CHP unit

237

(2)

The 9-anthryl group attached to the CHP unit

239

(1)

The 1-naphthyl group attached to the NH unit

240

(2)

Sterically overcrowded aminophosphonates

242

(4)

Variations of 1H-NMR spectra from-CHP-NH-fragments with substituent pattern, temperature, solvent and protonation

246

(14)

α-N-(4-fluorophenyl)amino-α-phenylmethanephosphonic acid diethyl ester

246

(5)

Classification of-CHP-NH-spectra

251

(1)

Attempts to interpret the results

251

(2)

Conformational analysis of α-N-(4-trifluoromethylphenyl)amino-α-phenylmethanephosphonic acid diethyl ester

253

(6)

Bulky aromatic substituents in Ar1 and Ar2

259

(1)

Heterocyclic aminophosphonates

260

(2)

Aromatic ring current effects in an isomeric pair of naphthyl-substituted aminophosphonates

262

(3)

Bifunctional aminophosphonates

265

(4)

Structural considerations

265

(1)

The CHP-skeleton of bifunctional aminophosphonates

265

(2)

The P(O) (OCH3)2 groups from bifunctional aminophosphonates

267

(2)

Aminophosphinates

269

(7)

Solid state and molecular modelling of P-[α-N-(4-fluorophenyl)-amino-α-phenylmethyl]-P-(methyl) phosphinic acid n-butyl ester (2.1-D1)

271

(3)

The 1H-NMR spectrum of P-[α-N-(4-fluorophenyl) amino-α-phenyl-methyl]-P-(methyl)phosphinic acid n-butyl ester (2.1-D1)

274

(2)

Some comments on phosphonic and phosphinic acids

276

(4)

References

280

(5)

Structure and Stability Constants of Metal Complexes in Solution

285

(42)

Tamas Kiss

Istvan Lazar

Introduction

285

(1)

Phosphonic derivatives of amino acids and related compounds

286

(11)

Acid-base chemistry

286

(1)

Metal-binding capabilities

287

(10)

Phosphono derivatives of dipeptides

297

(1)

Open-chain aminopolyphosphonates

298

(8)

Macrocyclic aminophosphonates and aminophosphinates

306

(15)

Acid-base chemistry

309

(3)

Metal complex formation

312

(5)

Biomedical applications

317

(1)

MRI contrast enhancement materials

317

(2)

Diagnostic use of fluorescent complexes

319

(1)

Paramagnetic complexes as shift reagents

320

(1)

Determination of intracellular metal ion concentration

320

(1)

Radioimmunoassay techniques

320

(1)

Determination of pH

321

(1)

Acknowledgements

321

(1)

References

321

(6)

X-Ray Crystallographic Studies

327

(36)

Nick Choi

Mary McPartlin

Introduction

327

(18)

Mono(aminophosphonic) and mono (aminophosphinic) acids

345

(4)

N-Acylated aminophosphonic and aminophosphinic acids

349

(2)

Diphosphonic and diphosphinic acids

351

(1)

Triphosphonic acids

351

(1)

Tetraphosphonic and tetraphosphinic acids

352

(7)

References

359

(4)

Mass Spectrometry and Gas Chromatography-Mass Spectrometry of Aminoalkanephosphonic Acids

363

(44)

Zbigniew H. Kudzin

M. Sochaki

Introduction

363

(1)

Derivatization of aminophosphonic acids and related compounds for GC and GC/MS

364

(8)

Mass spectrometric characterization of derivatized aminoalkanephosphonic acids and related copounds

372

(13)

Mass spectrometric characterization of O,O-substituted aminoalkanephosphonic acids

372

(1)

Mass spectrometric characterization of TMS-derivatives of aminoalkanephosphonates

372

(2)

Mass spectrometric characterization of O,O-dialkyl derivatives of aminoalkanephosphonates

374

(2)

Mass spectrometric characterization of O,O-dialkyl 1-(N-acylamino)-alkanephosphonates

376

(1)

Mass spectrometric characterization of O,O-dialkyl 1-(N-formylamino)-alkanephosphonates

377

(2)

Mass spectrometric characterization of O,O-dialkyl 1-(N-acetylamino)-alkanephosphonates

379

(1)

Mass Spectrometic Characterization of O,O-Dialkyl 1-(N-trifluoroacetylamino)-alkanephosphonates

379

(3)

Mass spectrometric characterization of other types of N-acylaminoalkanephosphonates

382

(1)

Chemical ionization mass spectrometry of O,O-dialkyl 1-(N-acylamino)alkanephosphonates

382

(3)

Mass spectrometric characterization of underivatized aminoalkanephosphonic acids, partly protected aminoalkanephosphonic acids and related derivatives

385

(10)

Mass spectra of underivatized aminoalkanephosphonic acids

385

(1)

Chemical ionization mass spectra of aminoalkanephosphonic acids

385

(3)

Fast atom bombardment mass spectra of amino-and guanidino-alkanephosphonic acids

388

(2)

Mass spectra of N-acylaminoalkanephosphonic acids

390

(5)

Mass spectrometric characterization of phosphonopetides

395

(9)

EI mass spectra of protected phosphonopeptides

397

(2)

FAB mass spectra of protected phosphonopeptides

399

(2)

FAB mass spectra of unprotected phosphonopeptides

401

(3)

References

404

(3)

The Biological Activity of Phosphono-and Phosphinopeptides

407

(36)

Pawel Kafarski

Barbara Lejczak

Antibacterial phosphonopeptides

408

(3)

Inhibition of proteases

411

(16)

Inhibitors of serine proteases

412

(5)

Inhibitors of metalloproteases

417

(8)

Inhibitors of aspartic proteases

425

(1)

Inhibitors of cysteine proteases

426

(1)

Inhibitors of β-lactamase

427

(1)

Inhibitors of ligases

427

(1)

Inhibitors of phosphotyrosyl-dependent signal transduction

428

(3)

Analogues of methotrexate

431

(3)

Other actvities

434

(1)

Catalytic antibodies (abzymes)

434

(1)

References

435

(8)

Aminophosphonic and Aminophosphinic Acids and their Derivatives as Agrochemicals

443

(40)

Harry R. Hudson

Introduction

443

(1)

Commercially available agrochemicals and their analogues

444

(10)

Glyphosate

445

(4)

Glufosinate and Bilanafos

449

(5)

Related Aminocarbonylphosphonic Acids

454

(1)

Biologically active aminophosphonic and aminophosphinic acids as candidate agrochemicals

454

(20)

Introduction

454

(1)

Plant-growth Regulators and Herbicides

455

(1)

Aminoalkane-phosphonic and-phosphinic acids

455

(3)

Aminocycloalkyl-phosphonic acids and-phosphine oxides

458

(1)

N-Arylaminoalkyl-phosphonates,-phosphinates, and-phosphine oxides

458

(1)

Amino(aryl)alkyl-phosphonic and-phosphinic acids

459

(2)

Phosphono-and phosphinopeptides

461

(1)

N-Phosphonoacetylamines, guanidino derivatives, and isoxazole-substituted aminoethylphosphonates

462

(1)

Aminomethylenebisphosphonic acids

463

(2)

Fungicides

465

(1)

Introduction

465

(1)

N-(ω-Guanidinoalkyl)-and N-(ω-aminoalkyl)-aminoalkane-phosphonic and-phosphinic acids

466

(1)

Aminoalkane-phosphonic and-phosphinic acids

467

(2)

Amino(aryl)alkyl-phosphonic and-phosphinic acids

469

(1)

Phosphonopeptides

470

(1)

Insecticides and related compounds

471

(1)

Summary and Prospects

472

(2)

Acknowledgement

474

(1)

References

474

(9)

Neuroactive Aminophosphinic and Aminophosphinic Acid Derivatives

483

(54)

David Jane

Introduction

483

(1)

Ionotropic glutamate receptors

484

(21)

Introduction

484

(2)

The NMDA receptor complex

486

(1)

NMDA receptor subtypes

487

(1)

NMDA recepter agonists

488

(2)

Competitive NMDA receptor antagonists

490

(4)

Radioligands for the glutamate recognition site of the NMDA receptor

494

(1)

Molecular modelling studies

494

(1)

Subtype selectivity of competitive NMDA receptor antagonists

495

(1)

Antagonists binding to the glycine co-agonist site of the NMDA receptor

496

(1)

Therapeutic applications of NMDA receptor antagonists

497

(1)

AMPA and kainate receptors

498

(3)

AMPA and kainate receptor agonists

501

(1)

AMPA and kainate receptor antagonists

501

(3)

Therapeutic utility of AMPA and kainate antagonists

504

(1)

Metabotropic glutamate receptors

505

(11)

Introduction

505

(3)

Group I selective agonists and antagonists

508

(2)

Group II selective agonists and antagonists

510

(1)

Group III selective agonists and antagonists

511

(4)

The QUIS effect

515

(1)

Phospholipase D coupled mGlu receptors

516

(1)

Therapeutic utility of mGlu receptor agonists and antagonists

516

(1)

Gaba receptor pharmacology

516

(9)

Introduction

516

(1)

GABAB receptor agonists and antagonists

517

(4)

GABAC receptor agonists and antagonists

521

(2)

GABA uptake inhibitors

523

(1)

Antagonists of the strychnine-sensitive glycine receptor

524

(1)

Concluding remarks

525

(1)

Acknowledgements

525

(1)

References

526

(11)

Aminophosphonic and Aminophosphinic Acid Derivatives in the Design of Transition State Analogue Inhibitors: Biomedical Opportunities and Limitations

537

(22)

Jozef Oleksyszyn

Proteolytic Enzymes: classification, mechanism of the proteolysis and implication for the design of transition analogue inhibitors

539

(2)

Drug development

541

(3)

Proteolytic enzymes as targets for drug design

544

(2)

Serine proteinases as targets for drug design. Biomedical opportunities for derivatives of α-aminoalkylphosphonic acid diphenyl esters

546

(3)

Human neutrophil elastase (HNE)

549

(1)

Dipeptidyl peptidase IV (DPP IV/D26)

550

(2)

Human heart chymase

552

(1)

Human cytomegalovirus protease

553

(1)

Granzymes

553

(2)

Proteolytic enzymes from larvae of the fire ant, Solenopsis invicta

555

(1)

References

556

(3)

Aminophosphonic and Aminophosphinic Acids in the Design and Synthesis of HIV Protease Inhibitors

559

(20)

Anusch Peyman

Introduction

559

(2)

Linear Inhibitors of HIV protease

561

(4)

C2-Symmetric Inhibitors of HIV protease

565

(8)

Non-peptide inhibitors of HIV protease

573

(2)

Conclusions

575

(1)

References

575

(4)

Aminophosphonic Acid Derivatives as Antithrombotic Agents

579

(18)

Donovan St. C. Green

Emmanuel Skordalakes

Michael F. Scully

John J. Deadman

Introduction

579

(2)

Studies of the Mechanism of Inhibition of Thrombin by Peptidylphosphonates

581

(2)

Routes to Dialkyl and Diaryl α-Aminophosphonates as Precursors for Thrombin Inhibitors

583

(1)

Tripeptidylphosphonates as Thrombin Inhibitors

584

(2)

Determination of Ki and Mechanism of Inhibition of Thrombin

586

(1)

Kinetics of the Slow Binding Phase (k2, k-2, and ki,) of Thrombin Inhibition by Z-Dpa-Pro-MpgP (OPH)2

586

(1)

Fitting generated values for A0 (initial absorbance), Vo (initial velocity), and Vs (final steady state velocity)

587

(2)

Specificity of Z-Dpa-Pro-MpgP (OPh)2 for Thrombin

589

(1)

Analysis of the Interaction of Z-D-Dpa-Pro-MpgP (OPh)2 with Human Thrombin by Crystallography

590

(2)

O,O-Dialkyl Dipeptidyl-ψ-(carboxy) benzylphosphonates as Novel Thrombin Inhibitors

592

(2)

Conclusions

594

(1)

References

594

(3)

Aminophosphonic and Aminophosphinic Acid Derivatives as Inhibitors of Human Collagenase

597

(24)

Roger Markwell

Human collagenase (MMP-1) and the matrix metalloproteinase (MMP) family

597

(1)

Potential therapeutic indications for MMP inhibitors

598

(1)

Structural characterisation of the MMP's

598

(1)

Design of collagenase inhibitors

599

(1)

Aminophosphonic acid derivatives as collagenase inhibitors

600

(6)

Proposed binding of an aminophosphonic acid inhibitor to collagenase (MMP-1)

606

(3)

Aminophosphinic acid derivatives as collagenase inhibitors

609

(6)

Comparison of aminophosphonic acid based inhibitors with other structural types

615

(2)

References

617

(4)

Index

621

Kids

Men

Unisex

Women

For You

For Your Car

For Your Home

For Your Pet

For Your Tech

Artwork

Cooking Essentials

Games

Gift Wraps

Holiday

Home Decor

Mascot

Office Decor

Outdoor/Recreation

Sporting

Graduation Gear

Graduation Gifts

Art Supplies

For Your Office

Medical Supplies

Office Supplies

School Supplies

Aminophosphonic and Aminophosphinic Acids Chemistry and Biological Activity

Buy New

Rent Textbook

Used Textbook

eTextbook

Summary

Author Biography

Table of Contents

Aminophosphonic and Aminophosphinic Acids Chemistry and Biological Activity

Buy New

Rent Textbook

Used Textbook

eTextbook

Summary

Author Biography

Table of Contents

Digital License