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Aim: A series of 1,3,4-thiadiazole himachalene hybrids were prepared from the treatment of a himachalen-4-one thiosemicarbazone derivative with N-aryl-C-ethoxycarbonyl-nitrilimines and diarylnitrilimines via a 1,3-dipolar cycloaddition reaction. Materials & methods: The structures were confirmed by NMR, IR and high-resolution mass spectroscopy (HRMS). Results & conclusion: The newly synthesized hybrid compounds were tested for their in vitro antitumor activities against a panel of cancer cell lines including fibrosarcoma (HT-1080), lung carcinoma (A-549) and breast carcinoma (MCF-7 and MDA-MB-231). Among the tested products, 4a showed excellent activity against the HT-1080 and MCF-7 cell lines with IC50values of 11.18 ± 0.69 and 12.38 ± 0.63 μm, comparable to that of the reference drug. Docking results confirmed that the active inhibitors were well accumulated in the mushroom tyrosinase active site. Flow cytometry analysis indicated that hybrid 4a induced apoptosis and cell cycle arrest in the G0/G1phase. Molecular modeling studies affirmed the intercalative binding of compound 4a in the active site.

This study aimed to analyze the cytotoxic and apoptotic effects of isoxazoline derivatives with monoterpene scaffold

In the current study, natural (R)-carvone was used as starting material for the efficient synthesis of several 1,2,3-triazole derivatives. The produced products were obtained in good yields and characterized by

The present work focuses on the synthesis, structural characterization and electrochemical investigation of some heterocyclic compounds prepared from d -limonene. Firstly, 3-acetylisoxazoline was synthesized from d -limonene, this precursor is then converted to its thiosemicarbazone derivatives which were then cyclized to produce their corresponding thiazolidine-4-ones. The obtained compounds were characterized by FT-IR, 1H NMR, 13C NMR and mass spectrometric techniques. Further, DFT quantum chemical studies were also used to interpret the structural properties of the compounds using the B3LYP/6–311++G (d, p) basis set. The obtained results from experimental and theoretical studies were in good agreement showing that compounds bearing both isoxazoline and thiazolidine-4-one moieties act as good corrosion inhibitors for stainless steel in 1 M sulfuric acid.

A new series of diverse triazoles linked to the hydroxyl group of totarol were synthesized using click chemistry approach. The structures of these compounds were elucidated by HRMS, IR and NMR spectroscopy. The structure of compound 3 g was also confirmed by x-ray single crystal diffraction. The cytotoxicity of these compounds was evaluated by the MTT method against four cancer cell lines, including fibrosarcoma HT-1080, lung carcinoma A-549 and breast adenocarcinoma (MDA-MB-231 and MCF-7), and the results indicated that all compounds showed weak to moderate activities against all cancer cell lines with IC50 values ranging from 14.44 to 46.25 μM. On the basis of our research the structure–activity relationships (SAR) of these compounds were discussed. This work provides some important hints for further structural modification of totarol towards developing novel and highly effective anticancer drugs respectively. It is interesting to note that compound 3 g indicated a very significant cytotoxicity against HT-1080 and A-549 cell lines. The molecular docking showed that compound 3 g activated the caspase-3 and inhibited tubulin by forming stable protein–ligand complexes.

A novel series of 1,2,3-triazole-thiazolidinone-carvone hybrid compounds has been designed and synthesized using the copper-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition (CuAAC) process based on (R)-Carvone-O-propargylated 5-hydroxybenzylidene-thiazolidin-4-one derivative as starting material. All compounds were characterized and identified based on their NMR and HRMS spectroscopic data. HMBC correlations confirm that under the CuAAC reaction conditions, only the 1,4-disubstituted triazole regioisomers were formed. The targeted 1,2,3-triazole-thiazolidinone-carvone hybrids and their precursors were evaluated for their cytotoxic activity against four human cancer cell lines, including fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast carcinoma (MCF-7 and MDA-MB-231). The obtained data showed that most of these compounds have moderate anti-proliferative activity with IC50 values between 15.04 ± 0.71 and 42.22 ± 1.20 µM. The mechanism of action of the most active compounds 14e and 14f suggested that they induce apoptosis through caspase-3/7 activation, and the compound 14e elicited S-phase arrest, while compound 14f evoked G2/M phase blockade. The molecular docking confirmed that compounds 14e and 14f were nicely bonded with caspace-3 leading up to stable protein-ligand complexes.

The title compound, C22H28O3, was prepared by a direct acetylation reaction of naturally occurring totarolenone. The molecule contains three fused rings, which exhibit different conformations. The central ring has a half-chair conformation, while the non-aromatic oxo-substituted ring has a screw-boat conformation. In the crystal, molecules are linked by C—H...O hydrogen bonds and C—H...π interactions, forming sheets parallel to the bc plane. The carbonyl O atoms and the C atom at the 6-position of the cyclohexene ring are each disordered over two sets of sites with major occupancy components of 0.63 (7) and 0.793 (14), respectively.

This article describes firstly the synthesis of a new series of isoxazole 5a-e from p-methoxythymol, extracted from Tetraclinis Articulata, as starting material involving 1,3-dipolar cycloaddition reaction and secondly a detailed study of the molecular packing and intermolecular interactions in crystals of five related 5-((2-isopropyl-4-‑methoxy‑5-methylphenoxy)methyl)-3-phenylisoxazole derivatives. All compounds were synthesized and subjected to solid state characterization by single-crystal X-ray diffraction analysis, and to studies with the use of NMR and Hirshfeld surface analysis. All structures display intermolecular C—H···O hydrogen bonding and C—H···π interactions, forming layers in the crystal lattice. The crystal structures of compounds 5a; 5c and 5d are consolidated by π—π interactions. Hirshfeld surface analysis, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different intermolecular contacts within the supramolecular structure. The most important contributions for the crystal packing are from H···H, H···C/C···H and O···H/H···O interactions. Additionally, DFT calculations have been used to analyze the electronic and geometric frontier molecular orbital and Molecular Electrostatic Potential map analyses of the compounds were produced using the optimized structures.

The title compound, an hemisynthetic product, was obtained by the tosyl­ation reaction of the naturally occurring meroterpene p-meth­oxy­thymol 1., The title compound, C18H22O4S, an hemisynthetic product, was obtained by the tosyl­ation reaction of the naturally occurring meroterpene p-meth­oxy­thymol. The mol­ecule comprises a tetra­substitued phenyl ring linked to a toluene­sulfonate through one of its O atoms. In the crystal, C—H⋯O and C—H⋯π inter­actions link the mol­ecules, forming a three-dimensional network.