Synthesis and Evaluation of Novel Cyclopropane Nucleoside as Potential Tube Formation Agents.

Five novel nucleoside analogs with mono or bis-hydroxymethylated cyclopropane rings at the N(9-)position of the 2-chloroadenine moiety (2-chloro-carbocyclic oxetanocin A ICOA-CII analog) were synthesized and evaluated using human umbilical vein endothelial cells. All the prepared compounds (2a-e) showed good to moderate activity with angiogenic potency. cis-2'-(Hydroxymethyl)cycloprop-l'-yl derivative (2b) at 100,mu m had greater angiogenic activity than the other compounds did, with relative tube areas of 2.71 +/- 0.45 (mean standard deviation (S.D.)), which was superior to the potency of COA-CI (2.30 +/- 0.59).