53066-15-2Relevant articles and documents
New copper(II) complexes with isoconazole: Synthesis, structures and biological properties
Dulcevscaia, Galina M.,Kravtsov, Victor Ch.,Macaev, Fliur Z.,Duca, Gheorghe G.,Stingachi, Eugenia P.,Pogrebnoi, Serghei I.,Boldescu, Veaceslav V.,Clapco, Steliana F.,Tiurina, Janeta P.,Deseatnic-Ciloci, Alexandra A.,Lipkowski, Janusz,Liu, Shi-Xia,Decurtins, Silvio,Baca, Svetlana G.
, p. 106 - 114 (2013/06/05)
There is an increasing demand for novel metal-based complexes with biologically relevant molecules in technology and medicine. Three new Cu(II) coordination compounds with antifungal agent isoconazole (L), namely mononuclear complexes [CuCl2(L)2] (1), and [Cu(O2CMe) 2(L)2]·2H2O (2) and coordination polymer [Cu(pht)(L)2]n (3) (where H2pht-o-phthalic acid) were synthesized and characterized by IR spectroscopy, thermogravimetric analysis and X-ray crystallography. X-ray analysis showed that in all complexes, the isoconazole is coordinated to Cu(II) centres by a N atom of the imidazole fragment. In complex 1, the square-planar environment of Cu(II) atoms is completed by two N atoms of isoconazole and two chloride ligands, whereas the Cu(II) atoms are coordinated by two N atoms from two isoconazole ligands and two O atoms from the different carboxylate residues: acetate in 2 and phthalate in 3. The formation of an infinite chain through the bridging phthalate ligand is observed in 3. The biosynthetic ability of micromycetes Aspergillus niger CNMN FD 10 in the presence of the prepared complexes 1-3 as well as the antifungal drug isoconazole were studied. Complexes 2 and 3 accelerate the biosynthesis of enzymes (β-glucosidase, xylanase and endoglucanase) by this fungus. Moreover, a simplified and improved method for the preparation of isoconazole nitrate was developed.
Asymmetric chemoenzymatic synthesis of miconazole and econazole enantiomers. the importance of chirality in their biological evaluation
Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Malpartida, Francisco,Gotor, Vicente
supporting information; experimental part, p. 2115 - 2122 (2011/05/19)
A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.
