Molbank — Open Access Journal

Stille coupling of 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) with tributyl(3-n-hexylthien-2-yl)stannane and Pd(Ph₃P)₂Cl₂ in PhMe at ca. 20 °C, for 24 h gave 3-chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one (9) with a 60% yield. The latter is a potentially useful building block for the synthesis of oligomeric and polymeric donors for organic photovoltaics. Full article

The title compound 5′(Z)-benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate was synthesized with high chemo-, regio-, and stereoselectivity by 5-exo-dig cycloisomerization of methyl 2α-phenylpropynyl-3-oxolup-20(29)-en-28-oate with use of KN(SiMe₃)₂-DME. The novel betulinic acid derivative was fully characterized by conventional analytical methods and all proton and carbon signals have been completely assigned by 2D-NMR experiments. Full article

We synthesized a novel compound, 5-(6-hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methylphenyl acetate, in a good yield by oxidation of 1-O-acetyl-xanthorrizol using potassium permanganate in acidic condition. The structure was elucidated by Fourier Transform Infrared (FTIR), ¹H-Nuclear Magnetic Resonance (NMR) and ¹³C-NMR, two-dimensional (2D)-HSQC, Distortionless Enhancement by Polarization Transfer (DEPT), 2D-Heteronuclear Multiple Bond Correlation (HMBC), and High-Resolution Mass Spectra (HRMS) spectral data. Full article

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a cardioprotective phytochemical occurring in many plant products. In this study, a new series of imine congeners of resveratrol has been synthesized in which the imine moiety replaced the double bond in the structure of resveratrol. In addition, the in vitro antiplatelet activity of these resveratrol derivatives has been evaluated against adenosine diphosphate (ADP), arachidonic acid (AA), and collagen as platelet aggregation inducers. In general, the synthesized compounds were active as antiplatelet agents, and, therefore, the imine functional group may be considered as an effective replacement for a double bond in resveratrol for developing new and promising antiplatelet drugs. Full article

The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (¹H-NMR and ¹³C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), and elemental analysis. The functionalization of the pyridine was achieved by the palladium-catalyzed Suzuki–Miyaura carbon–carbon cross-coupling reaction that afforded the target compound. Full article

The title quinoline derivative, 5-chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline, was synthesized in a common three-step procedure from 5-chloro-8-hydroxyquinoline using O-propargylation reaction/copper-catalyzed 1,3-dipolar cycloaddition sequence. The structure of the compound was fully characterized by FT-IR, ¹H- and ¹³C-NMR, GC-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The hybrid obtained could be an interesting model for antifungal bio-essays or a suitable precursor in the synthesis of more complex triazolyl-quinoline hybrids, potential pharmacological agents. Full article

A derivative of dihydrotetrazolopyrimidine has been successfully synthesized through a cyclocondensation reaction between a chalcone derivative with 5-aminotetrazole. The molecular structure of the title compound was established based on Fourier transform infrared spectra (FTIR), high-resolution mass spectrometry (HRMS), 1D and 2D nuclear magnetic resonance (NMR) spectrum. Full article

1-(2-Hydroxyethyl)imidazolidine-2-thione (1) was obtained as a product from an in situ reaction between N-(2-hydroxyethyl)ethylenediamine, carbon disulfide, potassium hydroxide, and di(4-fluorobenzyl)tin dichloride. Compound 1 was characterized by IR, UV, ¹H, ¹³C{¹H}, and 2D (COSY, NOESY, HSQC, and HMBC) NMR spectroscopies. The cyclic molecular structure was confirmed by single crystal X-ray crystallography which showed the five-membered ring to be non-planar and the π-electron density to be localized over the CN₂S chromophore. In the crystal, thioamide–N–H^…O(hydroxy) and hydroxy–O–H^…S(thione) hydrogen bonds lead to supramolecular layers in the bc-plane. Full article

N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) was synthesized in a yield of 88% from an acid-catalyzed reaction of 5-methyl-1-phenyl-1H-1,2,3- triazole-4-carbohydrazide and 4-methoxybenzaldehyde in ethanol under reflux for 2.5 h. The structure of 3 was confirmed by the data obtained from infrared, nuclear magnetic resonance, mass spectroscopy, single crystal X-ray diffraction, and microanalysis. Full article

The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by ¹H and ¹³C-NMR spectroscopy as well as by elemental analyses and HR-MS. Owing to its chelating properties, this new terpyridine molecule was tested as a ligand in a metal-catalyzed reaction: The Ni-catalyzed dimerization of benzyl bromide. Full article

N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) (¹H-NMR and ¹³C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high- performance liquid chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and elemental analysis. Full article

The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5’-nucleotidase, which has been considered as a target in designs for anti-cancer drugs. Full article

The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)₃PAu[SC(O-i-Pr)=NC₆H₄NO₂-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of 1 confirms the expected linear P–Au–S coordination geometry defined by thiolate-S and phosphane-P atoms. The nearly 7° deviation from linearity is ascribed to the close approach of the imine-bound phenyl group, indicative of a semi-localized Au^…π(arene) interaction. The three-dimensional molecular packing is consolidated by methyl- and tolyl-C–H^…O(nitro) and tolyl-C–H^…π(tolyl) interactions. Full article

A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the title compound was established using spectroscopic data FTIR, HRESI-MS, ¹H- and ¹³C-NMR. The anticancer activity against breast cancer cells line T47D and cervix cancer cells line HeLa was determined using an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Full article

The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl₂{P(CH₂CH₂CN)₃}(η⁶-p-cymene)] (p-cymene = p-CH₃C₆H₄ⁱPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl₂(η⁶-p-cymene)]₂ with tcep. The complex was characterised by a single-crystal X-ray structure determination as well as NMR spectroscopy, ESI mass spectrometry, and microelemental analysis. X-ray crystallography shows the ruthenium atom is coordinated by p-cymene in a η⁶-fashion, two chlorides and the phosphorus atom of the tcep ligand with the donor set defining a distorted octahedral geometry. The ESI mass spectrometry study reveals that the complex readily forms negative ions [M + Cl]⁻ and [2M + Cl]⁻ by association with a chloride ion. Full article