Synthesis and Validation of a Hydroxypyrone-Based, Potent, and Specific Matrix Metalloproteinase-12 Inhibitor with Anti-Inflammatory Activity In Vitro and In Vivo

<div>Reagents and conditions: (a) SOCl2; (b) H2O, Zn, and HCl (aq); (c) NaOH (aq), CH2O; (d) NaOH (aq), MeOH, and BnBr; (e) CHCl3, Et3N, DMSO, and SO3-pyridine; (f) acetone/water, sulfamic acid, and NaClO2; (g) THF, DCC, NHS, and 4-bromobenzylamine; (h) toluene, K2CO3 (aq), PPh3, Pd(OAc)2, and 1,1′-biphenyl-4-boronic acid; (i) MeOH/DCM, Pd/C, and H2.</div>

Mediators of Inflammation

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Scheme 1

Scheme 1: Synthesis and Validation of a Hydroxypyrone-Based, Potent, and Specific Matrix Metalloproteinase-12 Inhibitor with Anti-Inflammatory Activity In Vitro and In Vivo

Scheme 1 | Synthesis and Validation of a Hydroxypyrone-Based, Potent, and Specific Matrix Metalloproteinase-12 Inhibitor with Anti-Inflammatory Activity In Vitro and In Vivo 