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

  • Sakakibara Norikazu
    Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
  • Igarashi Junsuke
    Department of Cardiovascular Physiology, Faculty of Medicine, Kagawa University
  • Takata Maki
    Department of Pharmaco-Bio-Informatics, Faculty of Medicine, Kagawa University
  • Konishi Ryoji
    Department of Pharmaco-Bio-Informatics, Faculty of Medicine, Kagawa University
  • Kato Yoshihisa
    Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
  • Tsukamoto Ikuko
    Department of Pharmaco-Bio-Informatics, Faculty of Medicine, Kagawa University

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Abstract

<p>Five novel nucleoside analogs with mono or bis-hydroxymethylated cyclopropane rings at the N9-position of the 2-chloroadenine moiety (2-chloro-carbocyclic oxetanocin A [COA-Cl] analog) were synthesized and evaluated using human umbilical vein endothelial cells. All the prepared compounds (2ae) showed good to moderate activity with angiogenic potency. cis-2′-(Hydroxymethyl)cycloprop-1′-yl derivative (2b) at 100 µM 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-Cl (2.30±0.59).</p>

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