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. 2013 Jun 6;18(6):6620–6662. doi: 10.3390/molecules18066620

Figure 28.

N-Hydroxycinnamamide-based histone deacetylase inhibitors.

Figure 28

Reagent and conditions: (a) SOCI2, CH3OH, 98%. (b) (Boc)2O, Et3N, DCM, 80%. (c) LiAIH4, anhydrous THF, 0 °C, 86%. (d) PPh3, DEAD, anhydrous THF, 0 °C, 75% for 8a, 79% for 8b. (e) NH2OK, CH3OH, 51% for 9a, 49% for 9b. (f) HCI, anhydrous EtOAc, 90%. (g) (i) TFA, Et3N, DCM; (ii) R'COOH, TBTU, Et3N, THF, 52–75% for two steps. (h) (i) TFA, Et3N, DCM; (ii) R'SO2CI, Et3N, DCM, 60–76% for two steps. (i) NH2OK, CH3OH, 31–54%.