Sv. Makutova et al., MODIFICATION OF PYRIMIDINE NUCLEOSIDES WI TH THE USE OF NICOTINIC-ACID DERIVATIVES, Bioorganiceskaa himia, 21(4), 1995, pp. 289-295
Interaction of nicotinoyl chloride in situ with 2'-deoxyuridine, its 3
'-O-acetyl-, or 5'-O-trityl derivatives led to 3'-O-nicotinoyl-, 5'-O-
nicotynoyl-, 3',5'-di-O-nicotinoyl-, and N-3,3'-di-O-nicotinoyl-2'-deo
xyuridine. Similarly, 5'-O-nicotinoyl-6-azauridine resulted from the r
eaction of 2',3'-O-ethoxymethylidene-6-azauridine followed by the depr
otection. Reaction of no-5'-deoxy-2',3'-O-ethoxymethylidene-6-azauridi
ne with nicotinic acid in the presence of 2-ethoxy-1-ethoxycarbonyl-1,
2-dihydroquinoline followed by the cleavage of the 2',3' O-protecting
group gave 5'-deoxy-5'-nicotinamido-6-azauridine. The same compound wa
s obtained from 5'-amino-5'-deoxy-6-azauridine and N-succinimidyl nico
tinate. Structures of the compounds obtained were corroborated by H-1
NMR spectra. It is shown that 3',5'-di-O-nicotinoyl-2'-deoxyuridine an
d 5'-deoxy-5'-O-nicotinamido-6-azauridine are cytotoxic toward CaOv ce
lls in vitro (CE(50) 10(-5) M).