Oxidation of diclofenac catalyzed by manganese porphyrins: synthesis of novel diclofenac derivatives

authors	Neves, CMB; Simoes, MMQ; Domingues, MRM; Santos, ICMS; Neves, MGPMS; Paz, FAA; Silva, AMS; Cavaleiro, JAS
nationality	International
journal	RSC ADVANCES
keywords	AOT REVERSE MICELLES; HYDROGEN-PEROXIDE; CARBOXYLIC-ACIDS; DRUG-METABOLISM; METALLOPORPHYRIN CATALYSTS; EPOXIDATION REACTIONS; BIOMIMETIC OXIDATION; MN(III) PORPHYRINS; MASS-SPECTROMETRY; SODIUM PERIODATE
abstract	The oxidation of drugs using metalloporphyrins has been the subject of several studies in recent years. Diclofenac, one of the most frequently used anti-inflammatory drugs, is metabolized in humans by cytochrome P450 (CYP) enzymes to hydroxy-derivatives and to some metabolites resulting from oxidative decarboxylation. In this paper, the in vitro formation of several new diclofenac derivatives, initially resulting from oxidative decarboxylation, similar to what happens in vivo, is revealed. Chloro [5,10,15,20-tetrakis(2,6-dichlorophenyl) porphyrinato] manganese(III), [Mn(TDCPP) Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl) porphyrinato] manganese(III), [Mn(TPFPP) Cl], are tested in the presence of hydrogen peroxide at room temperature. The new products obtained are fully characterized, three of them being characterized in the solid state using X-ray diffraction studies.
publisher	ROYAL SOC CHEMISTRY
issn	2046-2069
year published	2012
volume	2
issue	19
beginning page	7427
ending page	7438
digital object identifier (doi)	10.1039/c2ra20801f
web of science category	Chemistry, Multidisciplinary
subject category	Chemistry
unique article identifier	WOS:000307185300016