[Synthesis of potential antimetabolites in a series of carbohydrate-modified pyrimidine 2'-deoxynucleosides].
The interaction of 3'-amino-2',3'-dideoxy- or 5'-amino-2',5'-dideoxy-5-substituted pyrimidine nucleosides with N-ethylmaleimide in DMF in the presence of Et3N gave two diastereomeric 2',3'-dideoxy-3'-(N-ethylsuccinimido)- or 2',5'-dideoxy-5'-(N-ethylsuccinimido)aminonucleosides in each reaction. For 3'-amino-5-trimethylsilyl- and 3'-amino-5-benzyloxymethyl-2',5'-dideoxyuridine diastereomeric 3'-(N-ethylsuccinimido)derivatives were separated by preparative TLC. Structures of synthesized analogs were confirmed by UV-, IR- and 1H-NMR spectra. It has been shown that modified nucleosides at 10(-5)-10(-4) M concentrations do not inhibit the thymidine incorporation into DNA of CaOv cells in vitro.
Bakhmedova
A A
AA
Iartseva
I V
IV
Mel'nik
S Ia
SIa
D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D002241:Carbohydrates / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D002855:Chromatography, Thin Layer; D015224:Dideoxynucleosides / Q000737:chemistry*; D005260:Female; D006801:Humans; D010051:Ovarian Neoplasms / Q000473:pathology; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D000964:Antimetabolites, Antineoplastic; D002241:Carbohydrates; D015224:Dideoxynucleosides; D011741:Pyrimidine Nucleosides