A Convenient Synthesis of Acyclic Adenosines with an Unsaturated Side Chain by Modification of 9-(2,3-O-Isopropylidene-D-Ribityl)Adenine |
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| Authors: | Kosaku Hirota Yasunari Monguchi Hironao Sajiki Chizuko Yatome Akio Hiraoka Yukio Kitade |
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| Institution: | 1. Laboratory of Medicinal Chemistry , Gifu Pharmaceutical University, Mitahora-higashi , Gifu, 502–0003, Japan;2. Department of Biomolecular Science, Faculty of Engineering , Gifu University, Yanagido , Gifu, 501–1112, Japan |
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| Abstract: | Abstract In expectation of discovering their antiviral activity, acyclic adenosine derivatives 7, 11, 12, and 16 were designed as analogs of neplanocin A (NPA) and L-eritadenine which are strong inhibitors of S-adenosyl-L-homocysteine hydrolase. The 1′,5′-seco-analog of 4′-deoxymethyl-NPA (DHCA) 7 was synthesized by dideoxygenation of 9-(2,3-O-isopropylidene-D-ribityl)adenine (2). Acyclic DHCA analogs 11 and 16 were obtained by Wittig reaction of the aldehyde 3 with Ph3P=CHCO2Et and Ph3P=CHCN, respectively. Hydrolysis of the ester 11 afforded a vinylog of L-eritadenine 12. The synthesized acyclic nucleosides 7, 10, and 11 were evaluated for antiviral activity, however, none of them showed any significant antiviral activity. |
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