Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York A Facile Synthesis of AICAR from Inosine Naoki Kohyama, Yukio Yamamoto*Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Yoshida, Kyoto 606-8501, JapanFax: +81(75)7536833; e-Mail: yukio@fischer.jinkan.kyoto-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract 5-Amino-1-β-d-ribofuranosylimidazole-4-carboxamide (AICAR; 1) (Figure [1] ) was efficiently prepared from inosine through its 1-alkoxymethylderivatives. The stability of these derivatives enabled their purification by column chromatography (silica gel). The operation ensured the high quality of 1, which was obtained in good yield through alkaline hydrolysis of the derivatives. Key words furans - inosine - nucleosides - hydrolyses - ring opening Full Text References References 1a Minakawa N. Takeda T. Sasaki T. Matsuda A. Ueda T. J. Med. Chem. 1991, 34: 778 1b Chern JW. Lin GS. Chen CS. Townsend LB. J. Org. Chem. 1991, 56: 4213 1c Fukukawa K. Shuto S. Hirano T. Ueda T. Chem. Pharm. Bull. 1986, 34: 3653 2a Song XM. Fiedler M. Galuska D. Ryder JW. Fernström M. Chibalin AV. Wallberg-Henriksson H. Zierath JR. Diabetologia 2002, 45: 56 2b Winder WW. Hardie DG. Am. J. Physiol. Endocrinol. Metab. 1999, 277: E1 3a Wu X. Motoshima H. Mahadev K. Stalker TJ. Scalia R. Goldstein BJ. Diabetes 2003, 52: 1355 3b Koistinen HA. Galuska D. Chibalin AV. Yang J. Zierath JR. Holman GD. Wallberg-Henriksson H. Diabetes 2003, 52: 1066 4 Musi N. Goodyear LJ. Current Drug Targets - Immune, Endocrine & Metabolic Disorders 2002, 2: 119 5a Nara T, and Misawa M. inventors; Jpn. Tokkyo Koho JP 46033196. 5b Sakai S, Niwa K, Sasaki H, Hirose Y, and Kinoshita K. inventors; Jpn. Tokkyo Koho JP 46028821. 5c Kanemitsu O, Akimoto T, Ito M, and Mimura S. inventors; Jpn. Tokkyo Koho JP 43020717. 6 Ferris JP. Devadas B. Huang CH. Ren WY. J. Org. Chem. 1985, 50: 747 7 Suzuki Y. Bull. Chem. Soc. Jpn. 1974, 47: 898 8 Ulrich SM. Sallee NA. Shokat KM. Bioorg. Med. Chem. Lett. 2002, 12: 3223 9 Shaw E. J. Am. Chem. Soc. 1961, 83: 4770