Synthesis of novel (1-alkanoyloxy-4-alkanoylaminobutylidene)-1,1-bisphosphonic acid derivatives

Turhanen, Petri A.; Vepsäläinen, Jouko

doi:10.1186/1860-5397-2-2

Cited by 9 publications

(4 citation statements)

References 26 publications

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“…36,56 For instance, alendronate 4 and pamidronate 5, have been prepared by this route 57 and served as precursors of substituted analogues like compounds 13 (Scheme 2). 58,59 Similarly, conjugates 14 have been prepared by condensation of 5 with the corresponding carboxylic acid. 60 Other conjugates include incorporation to nucleosides 61 and oligonucleotides.…”

Section: Reaction Of Carboxylic Acids With Phosphorous Reagentsmentioning

confidence: 99%

Chemical approaches to inhibitors of isoprenoid biosynthesis: targeting farnesyl and geranylgeranyl pyrophosphate synthases

et al. 2017

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Section: Reaction Of Carboxylic Acids With Phosphorous Reagentsmentioning

confidence: 99%

Chemical approaches to inhibitors of isoprenoid biosynthesis: targeting farnesyl and geranylgeranyl pyrophosphate synthases

et al. 2017

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“…This modified approach has been used to prepare N-acyl alendronate derivatives via a w-azide intermediate, reduction, acylation and finally deprotection (Scheme 5.55) [233]. Due to the poor solubility of alendronate in organic solvents, its direct N-acylation is carried out in higher yields by reaction of the disodium salt with carboxylic acid anhydrides or acyl chlorides in water [234,235]. Tetraethyl w-aminoalkylidene-1,1-bisphosphonates have been prepared from the tetraethyl methylene-bisphosphonate by a multistep procedure involving the synthesis of the corresponding w-hydroxyalkylidene-1,1-bisphosphonates and subsequent transformations.…”

Section: Synthesis Of G-aminophosphonates and Higher Homologs J219mentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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“…During the preparation of possibly bioreversible bisphosphonate derivatives, unexpected degradation of the P-C-P bridge under mild reaction conditions in two of the prepared etidronate derivatives was observed [13]. Earlier, Szymczak et al [14] have described the formation of H-phosphonate (also known as phosphite) and phosphate components from a phosphonate-phosphate compound.…”

Section: Introductionmentioning

confidence: 99%

“…Degradants from P-C-P bridge hydrolysis could be also found [13]. So it is desirable to develop the method which would be able to quantify not only analytes but also, simultaneously, their related substances.…”

Section: Introductionmentioning

confidence: 99%

Chemometric-assisted determination of some bisphosphonates and their related substances in pharmaceutical forms by ion chromatography with inverse UV detection

Zirojević

Jovic

Djurdjevic

et al. 2015

Acta Chromatographica

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Summary.A simple ion chromatographic (IC) method was developed and validated for simultaneous or individual determination of zoledronic, alendronic, pamidronic acids and their related substances in pharmaceutical formulation. The analytes were separated on Waters IC-Pak Anion HR analytical column with a nitric acid (3 mM) without any other additives, as mobile phase at a flow rate of 1.0 mL min −1 . Inverse UV detection was used at 240 nm. Important chromatographic factors that influence the chromatography responses were screened by 11/12 Pluckett-Burman design and their interaction were assayed by 2 3 full factorial design. The RP-HPLC method was optimized with the aid of LC-Simulator ® (ACD Labs, Toronto, Ontario, Canada) software. Validated method was successfully used for quantitative analysis of PAMIFOS ® , concentrate for infusion (Habitfarm AD, Ivanjica, Serbia), ZOMETA ® , powder for infusion (Novartis Pharma, Stein AG, Switzerland) and BONAP ® tablets (Hemofarm, Vrsac, Serbia). Total chromatographic analysis time per sample was approximately 6 min, which represents significant improvement over existing methods. Validation studies revealed that the method is specific, rapid, reliable, and reproducible. Calibration plots were linear over the concentration ranges 20-120 μg mL −1 and 0.1-2 μg mL −1 for bisphosponates and their related substances, respectively. The LODs were 8.7, 4.7, 2.5, 0.026 and 0.011 μg mL −1 for alendronate, pamidronate, zoledronate, phosphoric acid and phosphorous acid, respectively.

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Synthesis of novel (1-alkanoyloxy-4-alkanoylaminobutylidene)-1,1-bisphosphonic acid derivatives

Cited by 9 publications

References 26 publications

Chemical approaches to inhibitors of isoprenoid biosynthesis: targeting farnesyl and geranylgeranyl pyrophosphate synthases

Chemical approaches to inhibitors of isoprenoid biosynthesis: targeting farnesyl and geranylgeranyl pyrophosphate synthases

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Chemometric-assisted determination of some bisphosphonates and their related substances in pharmaceutical forms by ion chromatography with inverse UV detection

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