Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental analysis and FT-IR, 1H, and 13C-NMR spectroscopic methods. The crystal structure of the title compound 1 was determined by an X-ray single-crystal technique and an intramolecular C=O…H-N hydrogen bond and intermolecular C=S…H-N and C=S…H-C hydrogen interactions, which were observed for the crystal structure. The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted. Cyclic voltammetric (CV) experiments for the compounds were performed with the glassy carbon electrode. The reduction in potential values of the different functional groups such as nitro and cyano in title compounds were investigated using CV curves.

Chemoenzymatic Synthesis of Complex Phenylpropanoid Derivatives by the Botrytis cinerea Secretome and Evaluation of Their Wnt Inhibition Activity

In this study, a series of complex phenylpropanoid derivatives were obtained by chemoenzymatic biotransformation of ferulic acid, caffeic acid, and a mixture of both acids using the enzymatic secretome of Botrytis cinerea. These substrates were incubated with fungal enzymes, and the reactions were monitored using state-of-the-art analytical methods. Under such conditions, a series of dimers, trimers, and tetramers were generated. The reactions were optimized and scaled up. The resulting mixtures were purified by high-resolution semi-preparative HPLC combined with dry load introduction. This approach generated a series of 23 phenylpropanoid derivatives, 11 of which are described here for the first time. These compounds are divided into 12 dimers, 9 trimers (including a completely new structural scaffold), and 2 tetramers. Elucidation of their structures was performed with classical spectroscopic methods such as NMR and HRESIMS analyses. The resulting compound series were analyzed for anti-Wnt activity in TNBC cells, with several derivatives demonstrating specific inhibition.

Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties

A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in optoelectronics. The methodology used turned out to be useful regardless of the type of five-membered ring or the nature of the individual substituents. All the products were identified by spectroscopic methods, and the target compounds were tested for luminescent properties. This study showed that all the synthesized highly-conjugated triazoles exhibited luminescence; in particular, one derivative, 3,6-bis(4-(5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl)phenyl)-1,2,4,5-tetrazine (13b), showed strong fluorescence emission and ahigh quantum yield close to 1.

Monitoring Catalytic 2-Propanol Oxidation over Co3O4 Nanowires via In Situ Photoluminescence Spectroscopy

Spectroscopic methods enabling real-time monitoring of dynamic surface processes are a prerequisite for identifying how a catalyst triggers a chemical reaction. We present an in situ photoluminescence spectroscopy approach for probing the thermo-catalytic 2-propanol oxidation over mesostructured Co3O4 nanowires. Under oxidative conditions, a distinct blue emission at ~420 nm is detected that increases with temperature up to 280 °C, with an intermediate maximum at 150 °C. Catalytic data gained under comparable conditions show that this course of photoluminescence intensity precisely follows the conversion of 2-propanol and the production of acetone. The blue emission is assigned to the radiative recombination of unbound acetone molecules, the n - π* transition of which is selectively excited by a wavelength of 270 nm. These findings open a pathway for studying thermo-catalytic processes via in situ photoluminescence spectroscopy thereby gaining information about the performance of the catalyst and the formation of intermediate products.

Nitrous Oxide Adsorption and Decomposition on Zeolites and Zeolite-like Materials

Decomposition of N2O on modified zeolites, crystalline titanosilicalites, and related amorphous systems is studied by the catalytic and spectroscopic methods. Zinc-containing HZSM-5 zeolites and titanosilicalites with moderate Ti/Si ratios are shown to exhibit a better catalytic performance in N2O decomposition as compared with conventionally used Cu/HZSM-5 zeolites and amorphous Cu-containing catalysts. Dehydroxylation of the HZSM-5 zeolite by calcination at 1120 K results in an enhancement of the N2O conversion. The mechanism of the reaction and the role of coordinatively unsaturated cations and Lewis acid sites in N2O decomposition are discussed on the basis of the spectroscopic data.

Syntheses, crystal structures and supramolecular assemblies of two Cu(II) complexes based on a new heterocyclic ligand: Insights through C─H•••Cl and π•••π interactions

A heterocyclic ligand, N3L [4-(1-methylimidazole)-2,6-di(pyrazinyl)pyridine] has been synthesized and characterized by several spectroscopic methods. The ligand (N3L) was then used for the preparation of two complexes, namely, [Cu(N3L)Cl2] (complex 1)...

Charantoside L, A New Cucurbitane-Type Glycoside from Momordica charantia L. with α-Glucosidase Inhibitory Activities

A new cucurbitane-type glycoside (1) and two known compounds (2-3) were isolated from the ethanol extract of the fruits of Momordica charantia L. Their chemical structures were determined as (19 S,23 E)-5 β­,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol 3 -O-β-D-allopyranoside (1), goyaglycoside d (2), and (19 S,23 E)-5 β,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol (3) on the basis of the extensive spectroscopic methods, including 1D, 2D NMR, HRESIMS, and in comparison with the reported data. Compounds 1 to 3 were evaluated for α-glucosidase inhibitory effects. Compounds 1 and 2 showed anti α-glucosidase activity with IC50 values of 134.12 ± 11.20 and 163.17 ± 13.71 µM, respectively, compared with the positive control, acarbose, IC50 160.99 ± 14.30 μM. Compounds 2 and 3 were first isolated from plant M. charantia growing in Vietnam.

Large interaction energy for the homodimer and the heterodimer extracted from the supramolecular chain of a bent trinuclear zinc(II) complex with a reduced Schiff base ligand

A bent trinuclear zinc complex, [Zn{ZnIL}2]•DMF {H2L = 2,2'-[(2,2-Dimethyl-1,3-propanediyl)bis(iminomethylene)]bis[6-methoxyphenol]} was synthesized and characterized by standard spectroscopic methods and X-ray diffraction analysis. The existence of coordinated amino groups and iodide counter...

Dihydrobenzofurans and Propynylthiophenes From the Roots of Eupatorium heterophyllum

Seven new dihydrobenzofurans and 2 new propynyl thiophenes were isolated from the roots of Eupatorium heterophyllum together with 13 known compounds. The compounds were characterized using spectroscopic methods including 2D NMR, infrared, and mass spectrometric techniques. Aerial parts of this plant have been known to contain various sesquiterpenoids and displayed high chemical diversity (several compounds isolated and/or identified) among their chemical constituents depending on the collection site. Nevertheless, we found that the chemical diversity in the roots was lower than in the aerial parts.