118578-86-2Relevant academic research and scientific papers
Design, synthesis and evaluation of the inhibitory selectivity of novel trans-resveratrol analogues on human recombinant CYP1A1, CYP1A2 and CYP1B1
Mikstacka, Renata,Rimando, Agnes M.,Dutkiewicz, Zbigniew,Stefanski, Tomasz,Sobiak, Stanislaw
, p. 5117 - 5126 (2012/10/30)
A series of trans-stilbene derivatives containing 4′-methylthio substituent were synthesized and evaluated for inhibitory activities on human recombinant cytochrome P450(s): CYP1A1, CYP1A2, and CYP1B1. CYP1A2-related metabolism of stilbene derivatives was estimated by using NADPH oxidation assay. Additionally, for CYP1A2 and CYP1B1 molecular docking analysis was carried out to provide information on enzyme-ligand interactions and putative site of metabolism. 3,4,5-Trimethoxy-4′-methylthio-trans-stilbene, an analogue of DMU-212 (3,4,5,4′-tetramethoxy-trans-stilbene) was an effective inhibitor of all CYP1 enzymes. On the other hand, 2,3,4-trimethoxy-4′-methylthio- trans-stilbene, appeared to be the most selective inhibitor of the isozymes CYP1A1 and CYP1B1, displaying extremely low affinity towards CYP1A2. Molecular modeling suggested that the most probable binding poses of the methylthiostilbene derivatives in CYP1A2 active sites are those with the methylthio substituent directed towards the heme iron. Products of CYP1A2-catalyzed oxidation of 2,4,5-trimethoxy-4′-methylthiostilbene and 3,4,5-trimethoxy-4′-methylthiostilbene were identified as monohydroxylated compounds. Other studied derivatives appeared to be poor substrates of CYP1A2. Structure-activity relationship analysis rendered better understanding of the mechanism of action of xenobiotic-metabolizing enzymes crucial at the early stage of carcinogenesis.
Synthesis, UV/vis spectra and electrochemical characterisation of arylthio and styryl substituted ferrocenes
Sorensen, Thomas J.,Nielsen, Merete F.
experimental part, p. 610 - 618 (2012/04/10)
Two series of substituted ferrocenes were synthesised using either the Horner-Wadswor th-Emmons reaction or monolithiation of ferrocene. The series consist of arylthio- and styryl-ferrocenes with different substituents in the para position of the aryl rings of the systems. The electronic communication was investigated by comparing the substituent effects in absorption spectroscopy and in cyclic voltammetry. A small substituent effect was found in the electronic transitions of the styryl substituted ferrocenes. The oxidation of the ferrocene derivatives showed clear substituent effects as illustrated by the linear Hammett plots. The effect was shown to be an order of magnitude larger in the arylthio-systems than in the styryl systems. It is suggested that the reason behind the large effect is a direct sulfur-iron orbital overlap. Versita Sp. z o.o.
New sulfonyl-containing materials for nonlinear optics: Semiempirical calculations, synthesis, and properties
Ulman, Abraham,Willand, Craig S.,K?hler, Werner,Robello, Douglas R.,Williams, David J.,Handley, Laura
, p. 7083 - 7090 (2007/10/02)
In this study we describe semiempirical calculations, synthesis, ground-state dipole moment measurements, and measurements of molecular second-order hyperpolarizability coefficients (β) for new stilbene and azobenzene derivatives containing a methylsulfonyl group as the electron acceptor. We show that theoretical calculations can be used to predict the trends for molecular hyperpolarizabilities between similar compounds and that these gas-phase calculations underestimate β values, probably as a result of the valence basis set used in the calculations. Whereas the sulfone group has been demonstrated to give molecular hyperpolarizabilities somewhat less than those of similar nitro compounds, the difference becomes less as the degree of conjugation is increased. The increased transparency in the visible spectrum and the synthetic flexibility may make sulfonyl compounds important for some applications.
Negative inotropic activity of para-substituted diethyl benzylphosphonates related to fostedil
Bellucci, Christina,Gualtieri, Fulvio,Chiarini, Alberto
, p. 473 - 478 (2007/10/02)
Several para-substituted diethyl benzylphosphonates related to the calcium antagonist diethyl 4-(2-benzothiazolyl)benzylphosphonate (fostedil) have been studied.They produce a dose-dependent negative inotropic effect on left atrial muscle isolated from guinea pig heart.Some of the compounds are equipotent or slightly more potent than fostedil and diltiazem taken as reference drugs.Structure-activity relationships are discussed.Keywords: calcium antagonists / p-substituted diethyl benzylphosphonates / cardiodepressant activity
