29529-79-1Relevant academic research and scientific papers
Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases
Zhang, Dong,Markoulides, Marios S.,Stepanovs, Dmitrijs,Rydzik, Anna M.,El-Hussein, Ahmed,Bon, Corentin,Kamps, Jos J.A.G.,Umland, Klaus-Daniel,Collins, Patrick M.,Cahill, Samuel T.,Wang, David Y.,von Delft, Frank,Brem, Jürgen,McDonough, Michael A.,Schofield, Christopher J.
supporting information, p. 2928 - 2936 (2018/04/19)
Metallo-β-lactamases (MBLs) enable bacterial resistance to almost all classes of β-lactam antibiotics. We report studies on enethiol containing MBL inhibitors, which were prepared by rhodanine hydrolysis. The enethiols inhibit MBLs from different subclasses. Crystallographic analyses reveal that the enethiol sulphur displaces the di-Zn(II) ion bridging ‘hydrolytic’ water. In some, but not all, cases biophysical analyses provide evidence that rhodanine/enethiol inhibition involves formation of a ternary MBL enethiol rhodanine complex. The results demonstrate how low molecular weight active site Zn(II) chelating compounds can inhibit a range of clinically relevant MBLs and provide additional evidence for the potential of rhodanines to be hydrolysed to potent inhibitors of MBL protein fold and, maybe, other metallo-enzymes, perhaps contributing to the complex biological effects of rhodanines. The results imply that any medicinal chemistry studies employing rhodanines (and related scaffolds) as inhibitors should as a matter of course include testing of their hydrolysis products.
The chelating behaviour of 3-(4-X-phenyl)-2-sulfanylpropenoic acids with the PbII ion - Relevance of the lone electron pair in the supramolecular structures of the 2:1 complexes
Casas, Jose S.,Castano, M. Victoria,Couce, Maria D.,Sanchez, Agustin,Sordo, Jose,Torres, M. Dolores,Vazquez Lopez, Ezequiel M.
, p. 5110 - 5120 (2013/10/22)
The interaction of 3-(4-X-phenyl)-2-sulfanylpropenoic acids [H 2(X-pspa); X = -F, -Cl, -Br, -I, -OCH3, -OCF3, -OH] with lead(II) acetate in an alcoholic medium was explored in the search for new chelating agents for the Pb2+ ion. The direct reactions afforded [Pb(X-pspa)] complexes in yields of 67 (X = -Br) to 95 % (X = -OCH 3). When the PbII/H2(X-pspa) reaction was performed in the presence of diisopropylamine (Q), the derivatives [HQ] 2[Pb(X-pspa)2] (X = Cl, Br) were obtained. All of the complexes were characterized by spectrometric (FAB-MS and ESI-MS) and spectroscopic (IR, 1H and 13C NMR spectroscopy) methods and these showed the permanence of the O,S coordination of the ligands to the metal ion in dimethyl sulfoxide (DMSO) solution. H2(Cl-pspa), [HQ]2[Pb(Cl-pspa)2] and [HQ]2[Pb(Br-pspa) 2] were also fully characterized in the solid state by X-ray diffraction. The importance of the stereochemically active lone electron pair of the PbII ion in the supramolecular arrangement of [HQ] 2[Pb(X-pspa)2] (X = Cl, Br) is discussed. The characteristics of complexes formed by 3-(4-X-phenyl)-2-sulfanylpropenoic acids with lead(II) cations have been explored both in the solid state and in solution. The importance of the stereochemically active lone electron pair of the PbII ion in the supramolecular arrangement of [HQ] 2[Pb(X-pspa)2] (X = Cl, Br; Q = diisopropylamine) is discussed. Copyright
ADDITION OF HETEROCYCLIC CH ACIDS TO THE C=N BOND OF AZOMETHINES
Pavlenko, N. I.,Marshtupa, V. P.,Klyuev, N. A.,Baskunov, B. P.
, p. 808 - 812 (2007/10/02)
The aminomethylation of oxindole, 1-phenyl-3-methyl-5-pyrazolone, and N-phenylrhodanine was studied.Derivatives of these CH acids were obtained as a result of aminomethylation.The addition products were subjected to acid and base hydrolysis; the correspon
