Fig. 2: Design and synthesis of thiazolyl ketones. | Nature Communications

Fig. 2: Design and synthesis of thiazolyl ketones.

From: Next generation thiazolyl ketone inhibitors of cytosolic phospholipase A2 α for targeted cancer therapy

Fig. 2

a Design of second generation thiazolyl ketones. b Synthesis of inhibitors. Reagents and conditions: (a) BrCH2COOEt, Et3N, CHCl3; (b) CH3(CH2)5Br, K2CO3, acetone; (c) BrCH2COOEt, or BrCH(CH3)COOEt, K2CO3, acetone; (d) DIBALH, Et2O; (e) i. NaOCl, TEMPO, NaBr, NaHCO3, EtOAc/PhCH3/H2O 3:3:0.5, −5 °C; ii. TBDMSCN, 18-crown-6, KCN, CH2Cl2; (f) HCl.H-L-Cys-OMe or HCl.H-L-Cys-OEt, CH3COO−NH4+, MeOH; (g) DBU, BrCCl3, CH2Cl2; (h) 4 N HCl/MeOH or 4 N HCl/Et2O; (i) Dess-Martin periodinane, CH2Cl2; (j) i. NaHSO3 4 N, CH2Cl2, ii. KCN 4 N, H2O/THF 1:1.

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