-transparent.png){kind=logo}
Groups of 5'-phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-acetylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene, or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonyl-phosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by the action of ammonia in methanol. All compounds were tested for inhibition of several viruses, including human herpes simplex virus type 2 and cytomegalovirus, but showed no activity. A few compounds insignificantly inhibited human immunodeficiency virus type 1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized the anti HIV action of 3'-azido-3'-deoxythymidine, thus indirectly showing that it could be partly hydrolyzed in cell culture to corresponding thymidine.
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
January 2002,
Bioorganicheskaia khimiia,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
January 2008,
Nucleic acids symposium series (2004),
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
March 1960,
Biochimica et biophysica acta,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
November 1987,
Bioorganicheskaia khimiia,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
January 2006,
Biochemistry. Biokhimiia,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
May 2001,
Current protocols in nucleic acid chemistry,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
February 2007,
Organic & biomolecular chemistry,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
August 2011,
Bioorganic & medicinal chemistry,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
January 1997,
Nucleic acids symposium series,
E A Shirokova, and
M V Ias'ko, and
A V Shipitsyn, and
A A Kraevskiĭ, and
M Ostrander, and
B O'Hara, and
P Baron, and
K Maclow, and
B Polsky
November 1965,
Il Farmaco; edizione scientifica,
