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Krystian Kołodziej

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Papers by Krystian Kołodziej

Research paper thumbnail of Aryl H-phosphonates. 19. New anti-HIV pronucleotide phosphoramidate diesters containing amino- and hydroxypyridine auxiliaries

European Journal of Medicinal Chemistry, 2018

We have designed a new type of AZT and ddU phosphoramidate diesters containing various combinatio... more We have designed a new type of AZT and ddU phosphoramidate diesters containing various combinations of 2-, 3-, 4-aminopyridine and 2-, 3-, 4-hydroxypyridine moieties attached to the phosphorus center, as potential anti-HIV pronucleotides. Depending on the pK a values of the aminopyridines and the hydroxypyridines used, alternative synthetic strategies based on Hphosphonate chemistry were developed for their preparation. Synthetic aspects of these transformations and the biological activity of the synthesized compounds are discussed.

Research paper thumbnail of Aryl <i>H-</i>Phosphonates 17: (<i>N-</i>Aryl)phosphoramidates of Pyrimidine Nucleoside Analogues and Their Synthesis, Selected Properties, and Anti-HIV Activity

Journal of Medicinal Chemistry, Sep 9, 2011

Research paper thumbnail of Electronic supplementary material

Research paper thumbnail of The loss of TEAH+ cation from certain nucleotide analogues

Collection Symposium Series, 2014

ABSTRACT During chromatographic purification and evaporation of solvents, triethylammonium salts ... more ABSTRACT During chromatographic purification and evaporation of solvents, triethylammonium salts of phosphate esters and amides may loose the cation yielding new species differing in chemical and physical properties

Research paper thumbnail of Aryl H-Phosphonates 17. Supporting Information

Research paper thumbnail of Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2′,3′-dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity

European Journal of Medicinal Chemistry, 2015

Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2',3'dideoxynucleoside ... more Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2',3'dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity

Research paper thumbnail of Aryl H-Phosphonates 17: (N-Aryl)phosphoramidates of Pyrimidine Nucleoside Analogues and Their Synthesis, Selected Properties, and Anti-HIV Activity

Journal of Medicinal Chemistry, 2011

Research paper thumbnail of The case of triethylammonium cation loss during purification of certain nucleotide analogues: a cautionary note

Analytical and Bioanalytical Chemistry, 2014

Nucleotides, their analogues, and other phosphate esters and phosphoramidates often contain the t... more Nucleotides, their analogues, and other phosphate esters and phosphoramidates often contain the triethylammonium cation as a counterion. We found that this may be lost during chromatographic purification or concentration of solutions, yielding products in acidic forms or containing sub-stoichiometric amounts of the counterion. This in turn may be detrimental, e.g., due to possible decomposition of a compound or inaccurate sample preparation. Correlations between the structure of studied compounds and their susceptibility for cation loss were analyzed. Modifications in preparative techniques were developed to obtain the studied compounds with stoichiometric anion to cation ratios.

Research paper thumbnail of Aryl H-phosphonates. 19. New anti-HIV pronucleotide phosphoramidate diesters containing amino- and hydroxypyridine auxiliaries

European Journal of Medicinal Chemistry, 2018

We have designed a new type of AZT and ddU phosphoramidate diesters containing various combinatio... more We have designed a new type of AZT and ddU phosphoramidate diesters containing various combinations of 2-, 3-, 4-aminopyridine and 2-, 3-, 4-hydroxypyridine moieties attached to the phosphorus center, as potential anti-HIV pronucleotides. Depending on the pK a values of the aminopyridines and the hydroxypyridines used, alternative synthetic strategies based on Hphosphonate chemistry were developed for their preparation. Synthetic aspects of these transformations and the biological activity of the synthesized compounds are discussed.

Research paper thumbnail of Aryl <i>H-</i>Phosphonates 17: (<i>N-</i>Aryl)phosphoramidates of Pyrimidine Nucleoside Analogues and Their Synthesis, Selected Properties, and Anti-HIV Activity

Journal of Medicinal Chemistry, Sep 9, 2011

Research paper thumbnail of Electronic supplementary material

Research paper thumbnail of The loss of TEAH+ cation from certain nucleotide analogues

Collection Symposium Series, 2014

ABSTRACT During chromatographic purification and evaporation of solvents, triethylammonium salts ... more ABSTRACT During chromatographic purification and evaporation of solvents, triethylammonium salts of phosphate esters and amides may loose the cation yielding new species differing in chemical and physical properties

Research paper thumbnail of Aryl H-Phosphonates 17. Supporting Information

Research paper thumbnail of Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2′,3′-dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity

European Journal of Medicinal Chemistry, 2015

Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2',3'dideoxynucleoside ... more Aryl H-Phosphonates 18. Synthesis, properties, and biological activity of 2',3'dideoxynucleoside (N-heteroaryl)phosphoramidates of increased lipophilicity

Research paper thumbnail of Aryl H-Phosphonates 17: (N-Aryl)phosphoramidates of Pyrimidine Nucleoside Analogues and Their Synthesis, Selected Properties, and Anti-HIV Activity

Journal of Medicinal Chemistry, 2011

Research paper thumbnail of The case of triethylammonium cation loss during purification of certain nucleotide analogues: a cautionary note

Analytical and Bioanalytical Chemistry, 2014

Nucleotides, their analogues, and other phosphate esters and phosphoramidates often contain the t... more Nucleotides, their analogues, and other phosphate esters and phosphoramidates often contain the triethylammonium cation as a counterion. We found that this may be lost during chromatographic purification or concentration of solutions, yielding products in acidic forms or containing sub-stoichiometric amounts of the counterion. This in turn may be detrimental, e.g., due to possible decomposition of a compound or inaccurate sample preparation. Correlations between the structure of studied compounds and their susceptibility for cation loss were analyzed. Modifications in preparative techniques were developed to obtain the studied compounds with stoichiometric anion to cation ratios.

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