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. Author manuscript; available in PMC: 2019 May 10.
Published in final edited form as: Eur J Med Chem. 2018 Apr 3;151:450–461. doi: 10.1016/j.ejmech.2018.04.006

Scheme 1.

Scheme 1

Synthetic route of newly designed compounds 11~16. Reagents and conditions: (a) DIPEA, DCM, 0~5 °C, 89%; (b) Zn, NH4Cl, EtOH/H2O, 80 °C, quant.; (c) 5-propylisoxazole-3-carboxylic acid (for 11) or 5-(furan-2-yl)isoxazole-3-carboxylic acid (for 12), HBTU, DIPEA, DCM, 0~5 °C. 68% for 11; 86% for 12; (d) 4-fluorobenzoyl chloride, pyridine (for 13) or 4-trifluorobenzoyl chloride (for 14), DCM, 0~5 °C, 67% for 13, quant. for 14; (e) 4-hydroxybenzaldehyde, NaBH3CN, MeOH, 80 °C, 85%; (f) 5-amino-2-methylphenol, tert-butyl nitrite, 38% HCl (aq.), K2CO3, MeOH/CH3CN/H2O, 0 °C, 78%.