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Synthesis, Characterization, Reactivity, Catalytic Activity, and Antiamoebic Activity of Vanadium(V) Complexes of ICL670 (Deferasirox) and a Related Ligand
Author(s) -
Maurya Mannar R.,
Sarkar Bithika,
Avecilla Fernando,
Tariq Saba,
Azam Amir,
Correia Isabel
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201501336
Subject(s) - chemistry , reactivity (psychology) , ligand (biochemistry) , medicinal chemistry , catalysis , acetylacetone , vanadium , denticity , ruthenium , halogenation , methoxide , stereochemistry , nuclear chemistry , metal , inorganic chemistry , organic chemistry , medicine , biochemistry , receptor , alternative medicine , pathology
The reactions of [V IV O(acac) 2 ] (acac = acetylacetonato) with two ONO tridentate ligands, 4‐[3,5‐bis(2‐hydroxyphenyl)‐1,2,4‐triazol‐1‐yl]benzoic acid (H 2 L 1 , I ) and 3,5‐bis(2‐hydroxyphenyl)‐1‐phenyl‐1,2,4‐triazole (H 2 L 2 , II ) in methanol lead to the formation of the oxidovanadium(V) complexes [V V O(µ‐L 1 )(OMe)] 2 ( 1 ) and [V V O(µ‐L 2 )(OMe)] 2 ( 2 ). In the presence of KOH/CsOH, they give the corresponding dioxidovanadium(V) complexes. The isolated complexes K(H 2 O)[V V O 2 (L 1 )] ( 3 ), K(H 2 O)[V V O 2 (L 2 )] ( 4 ), Cs(H 2 O)[V V O 2 (L 1 )] ( 5 ), and Cs(H 2 O)[V V O 2 (L 2 )] ( 6 ) along with 1 and 2 have been characterized by various spectroscopic techniques (FTIR; UV/Vis; 1 H, 13 C, and 51 V NMR), elemental analysis, thermal studies, MALDI‐TOF MS analysis, and single‐crystal analysis of 1a (complex 1 grown together with 4,4′‐bipyridyl). The oxidative bromination of thymol, catalyzed by these complexes, in the presence of KBr and HClO 4 with H 2 O 2 as an oxidant, gives 2‐bromothymol, 4‐bromothymol, and 2,4‐dibromothymol. The amounts of the catalyst, oxidant, KBr, HClO 4 , and the solvent were optimized for the maximum conversion of thymol. Both ligands and all complexes were tested in vitro for antiamoebic activity against the HM1:IMSS strain of Entamoeba histolytica by a microdilution method. The complexes are more potent amoebicidal agents than the standard drug metronidazole. Toxicity studies against a human cervical cancer cell line (HeLa) also confirm that these compounds are less cytotoxic than metronidazole.