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(A) Structure of the three NAD analogs carrying a pyridone moiety; (B,C) synthetic pathways developed for the pyridone containing NAD analogs [70]. Conditions: a) i. AMPCH2P, pyridine, DIC, rt, overnight, ii. nucleoside 51, 70 h, 65 °C, iii. H2O, TEA, 6 h, 65 °C; b) 80% TFA, 3 h, 0 °C; c) i. NH3 in MeOH, 48 h, rt; ii. MeOH, TMSCH2N2 then AcOH, 15 min, rt; d) dimethoxypropane, acetone, p-TsOH, 3 h, rt; e. NH3 in MeOH, 3 days, rt; f) HCO2H 50%, overnight, rt.
