Synthesis of carbocyclic nucleotides as potential substrates for thymidylate kinase

Nucleosides, Nucleotides and Nucleic Acids

Volumn 24, Issue 5-7, 2005, Pages 683-686

  Ludek, O R ^a   Meier, C ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Carbocyclic Nucleosides; CycloSal Pronucleotides; Mitsunobu Reaction; Nucleotides

Indexed keywords

2' DEOXY 3' AZIDOTHYMIDINE MONOPHOSPHATE; CARBA 2' DEOXY 3' THIOCYANATOTHYMIDINE MONOPHOSPHATE; CARBOCYCLIC NUCLEOSIDE; THYMIDINE PHOSPHATE; THYMIDYLATE KINASE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; ENANTIOMER; ENZYME PHOSPHORYLATION; ENZYME SUBSTRATE; HYDROLYSIS; MITSUNOBU REACTION; NUCLEOTIDE METABOLISM;

ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CARBON; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HYDROLYSIS; MODELS, CHEMICAL; NUCLEOSIDE-PHOSPHATE KINASE; NUCLEOTIDES; SUBSTRATE SPECIFICITY; THYMINE NUCLEOTIDES; ZIDOVUDINE;

EID: 26844475079     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1081/NCN-200060251     Document Type: Conference Paper

References (7)

1. Balzarini, J.; Naesens, L.; Aquaro, S.; Knispel, T.; Perno, C.-F.; De Clercq, E.; Meier, C. Intracellular metabolism of cycloSaligenyl 3′-azido-2′,3′-dideoxy-thymidine monophosphate, a prodrug of 3′-azido-2′,3′-dideoxythymidine (zidovudine). Mol. Pharmacol. 1999, 56, 1354-1361.
2. Meier, C. cycloSal-pronucleotides-design of chemical trojan horses. Mini Rev. Med. Chem. 2002, 2, 219-234.
3. Lavie, A.; Schlichting, I.; Vetter, I.R.; Konrad, M.; Reinstein, .J.; Goody, R.S. The bottleneck in AZT activation. Nat. Med. 1997, 3, 922-924.
4. Müller, H.C.; Meier, C.; Balzarini, J.; Reinstein, J. Novel nucleotide analogues as potential substrates for TmpK-a key enzyme in the metabolism of AZT. Nucleosides Nucleotides Nucleic Acids 2003, 5-8, 821-823.
5. Ludek, O.R.; Meier, C. New convergent synthesis of carbocyclic nucleoside analogues. Synthesis 2003, 13, 2101-2109.
6. Schreiber, S.L.; Ikemoto, N. Synthesis of chemically reactive analogues of AZT and their biological evaluation against HIV. Tetrahedron Lett. 1988, 28, 3211-3214.
7. Meier, C. 4H-[1.3.2]-benzodioxaphosphorin-2-nucleosyl-2-oxide-a new concept for lipophilic, potential prodrugs of biologically active nucleoside monophosphates. Angew. Chem., Int. Ed. Engl. 1996, 35, 70-72.