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Paper | Regular issue | Vol 85, No. 5, 2012, pp.1105-1116
Published online, 30th March, 2012
DOI: 10.3987/COM-12-12441
Novel Synthesis of Carbocyclic Oxetanocin Analogs (2-Alkoxy-C.OXT-A) and Their Tube Formation Activities of Human Umbilical Vein Endothelial Cells (HUVEC)

Norikazu Sakakibara, Ikuko Tsukamoto, Takashi Tsuruta, Maki Takata, Ryoji Konishi, and Tokumi Maruyama*

*Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki City, Kagawa, 769-2193, Japan

Abstract

We succeeded in the effective synthesis of five types of 2-alkoxy-C.OXT-A analogs (9, 10a–d) by applying the de novo synthesis of 2-alkoxyadenosine derivatives (2), which was developed in our laboratory. For these synthesized compounds, the angiogenic activity was evaluated using human umbilical vein endothelial cells. Four products (10a–d) enhanced the activity of the cell; in particular, 2-methoxy-C.OXT-A (10a) and 2-isopropoxy-C.OXT-A (10c) at a concentration of 100 μM exhibited the same or stronger potency than the vascular endothelial cell growth factor.