Chemistry and Application of H-Phosphonates is an excellent source
for those planning the synthesis of new phosphorus-containing
compounds and in particular derivatives containing a phosphonate,
phosphoramide or phosphonic acid diester group. The rich chemistry,
low cost and easy availability of diesters of H-phosphonic acid
makes them an excellent choice as synthone in a number of
practically important reactions.
Phosphonic acid esters are intermediates in the synthesis of
important classes of compounds such as alpha-aminophosphonic acids,
bisphosphonates, epoxyalkylphosphonates,
alpha-hydroxyalkylphosphonates, phosphoramides, poly(alkylene
H-phosphonate)s, poly(alkylene phosphate)s, nucleoside
H-phosphonates. The synthesis of each of these compound classes is
reviewed in detail.
Alpha-Aminophosphonic acids are an important class of biologically
active compounds, which have received an increasing amount of
attention because they are considered to be structural analogues of
the corresponding Alpha-amino acids. The utilities of
alpha-aminophosphonates as peptide mimics, haptens of catalytic
antibodies, enzyme inhibitors, inhibitors of cancers, tumours,
viruses, antibiotics and pharmacologic agents are well documented.
Alpha-Hydroxyalkanephosphonates are compounds of significant
biological and medicinal applications. Dialkyl
epoxyalkylphosphonates are of interest because of their use as
intermediates in the synthesis of bioactive substances, and as
modifiers of natural and synthetic polymers. Bisphosphonates are
drugs that have been widely used in different bone diseases, and
have recently been used successfully against many parasites.
Poly(alkylene H-phosphonate)s andpoly(alkylene phosphate)s are
promising, biodegradable, water soluble, new polymer-carriers of
drugs. Nucleoside H-phosphonates seem to be the most attractive
candidates as starting materials in the chemical synthesis of DNA
and RNA fragments. The 5'-hydrogen
phosphonate-3'-azido-2',3'-dideoxythimidine is one of the most
significant anti-HIV prodrug, which is currently in clinical
trials.
Chapters review the synthesis; physical and spectral properties
(1H, 13C, 31P and 17O NMR data); characteristic reactions;
important classes of compounds based on these esters of
H-phosphonic acid; their application as physiologically active
substances, flame retardants, catalysts, heat and light
stabilizers, lubricants, scale inhibitors, polymer-carriers of
drugs; preparation of H-phosphonate diesters and general procedures
for conducting the most important reactions.
* provides ideas for the synthesis of phosphonates, phosphoramides
and diesters of phosphonic acid (new phosphorus-containing
compounds)
* reviews structure, spectra and biological activity of
H-phosphonates and their derivatives
* examines new areas of application of phosphorus-containing
compounds