The design and synthesis of a new tumor-selective fluoropyrimidine carbamate, capecitabine

…, I Umeda, M Arasaki, C Murasaki, K Masubuchi…

Index: Shimma, Nobuo; Umeda, Isao; Arasaki, Motohiro; Murasaki, Chikako; Masubuchi, Kazunao; Kohchi, Yasunori; Miwa, Masanori; Ura, Masako; Sawada, Noriaki; Tahara, Hitoshi; Kuruma, Isamu; Horii, Ikuo; Ishitsuka, Hideo Bioorganic and Medicinal Chemistry, 2000 , vol. 8, # 7 p. 1697 - 1706

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Citation Number: 134

Abstract

To identify an orally available fluoropyrimidine having efficacy and safety profiles greatly improved over those of parenteral 5-fluorouracil (5-FU: 1), we designed a 5-FU prodrug that would pass intact through the intestinal mucisa and be sequentially converted to 5-FU by enzymes that are highly expressed in the human liver and then in tumors. Among various N4- substituted 5′-deoxy-5-fluorocytidine derivatives, a series of N4-alkoxycarbonyl ...