Scheme 1.
Synthesis of NO donor derivatives 10a–i. Reagents and conditions: (a) chloroactic acid, NaOH (aq), 60 °C, 4 h; (b) 30% H2O2, glacial acetic acid, rt, 2 h; (c) fuming HNO3, glacial acetic acid, 60 °C, 4 h; (d) corresponding diol, NaOH (aq), THF, rt, 2 h; (e) anhydride, DMAP/TEA, DCM, rt, 1 h; (f) sodium periodate, H2O, rt, 6 h; (g) Jones reagent, DCM, rt, 0.5 h; (h) 7a–i, EDCI, DMAP, DCM, rt, 8–12 h.