ISSN:
0170-2041
Keywords:
Prodrugs
;
Cytidine derivatives
;
Cytosine derivatives
;
Thymidine derivatives
;
Amphiphilic dinucleoside phosphates
;
Hydrogen phosphonate method
;
Liposomes
;
Nucleosides
;
Nucleotides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis and Properties of N4-Hexadecyl-2′-deoxycytidylyl-(3′-5′)-5-ethyl-2′-deoxyuridine and 2′-Deoxythymidylyl-(3′-5′)-N4-hexadecyl-1-β-D-arabinofuranosylcytosine, Two Representatives of a New Kind of ProdrugsThe gram-scale condensation of N4-hexadecyl-2′-deoxycytidine with the antiviral 5-ethyl-2′-deoxyuridine and of 2′-deoxythymidine with the antineoplastic N4-hexadecyl-1-β-D-arabinofuranosylcytosine via a 3′-5′-phosphodiester linkage using the hydrogen phosphonate method is described. The purity and the structure of the synthetic products were determined chromatographically (TLC, HPLC) and spectroscopically (MS-MS, 2D-NMR). The resulting amphiphilic dinucleoside phosphates represent two examples of a new kind of prodrugs in which lipophilic or hydrophilic nucleoside residues are applied for the masking of 5′-phosphorylated nucleoside analogues which are known as chemotherapeutics. The prodrugs are soluble in water and can also be incorporated together with matrix lipids into stable liposome dispersions.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940309
