One-step,stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Novel, functionalized octahydrochromane derivatives were synthesized in a single step via the Prins reaction. Enantiomerically pure (+)-isopulegol was reacted with benzaldehyde to stereoselectively yield the corresponding octahydro-2H-chromen-4-ol derivative containing five stereocenters. A total of 10 compounds were synthesized by altering the enantiomer of isopulegol and the substituted benzaldehyde, and the resulting enantiopure octahydrochromanes were screened in vitro against the cannabinoid receptor isoforms CB1 and CB2. Compounds containing an olefin at the C4 position [(+)-3c, (?)-3c, (?)-7c, (?)-9c and (?)-11c] of the octahydrochromane scaffold were found to exhibit reasonable displacement of [³H] CP55,940 from the CB receptors, whereas the corresponding hydroxy analogs [(+)-3a, (+)-3b, (?)-3a, (?)-3b and (+)-5a] had very little or no effect.     

Synthèse de copolymères greffés à base de polyéthylène—1

Polyethylene macromolecular free radical initiators, obtained by ozonization, are used to prepare graft copolymers with methyl methacrylate, styrene and vinyl chloride. The reactions parameters are the number of initiator groups (found by DPPH), peroxide and hydroperoxide proportions (respectively 36 and 64%), decomposition rate (K_d at 90° 10⁻¹sec⁻¹) and monomer concentration. The molecular structure of these copolymers is defined.     

Chelating Behaviour of Substituted 3-4 Aryl-Hydrazo-Pentane-2, 4-Dione: Part VI. Potentiometric and Infrared Studies of the Ligands and Their Divalent Metal Complexes

The dissociation constants of 3-phenylhydrazo-pentane-2, 4-dione and its o-, m-, p-carboxy derivatives, and the stability constants of complexes of divalent metal ions with the o-carboxy derivative are determined by pH-metric method. The ir-spectra of the ligands and some divalent metal complexes with the o-derivative are discussed.     

Isolation,identification, and keratinolytic activity of several feather-degrading bacterial isolates

Several feather-degrading bacterial isolates were isolated from Egyptian soil. These isolates were able to degrade chicken feather, when grown on basal medium containing 1% native feather as a source of energy, carbon, and nitrogen. Feather waste, generated in large quantities as a byproduct of commercial poultry processing, is nearly pure keratin, which is not easily degradable by common proteolytic enzymes. The isolates were identified according to the morphological characteristics, biochemical tests, and API 50 CHBBacillus system. Proteolytic and keratinolytic activities of these isolates were monitored throughout the cultivation of the bacterial isolates on feather. Resulting soluble proteins, which were released as a result of the biodegradation of feather, were demonstrated by SDS-PAGE.     

Matériaux composites à base de graves et de liants polymères II: Ozonisation du polyéthylène et dosage des hydropéroxydes et des péroxydes derivés

The study of the oxidation of low density polyethylene is carried out under fluidized conditions in air and ozone. Special attention is paid to the formation of peroxides and hydroperoxides. Their production is optimized according to various parameters (temperature, time, quantity of ozone, flow of the gaseous current) using an experimental design method. Peroxides and hydroperoxides are titrated by a colorimetric method using diphenylpicrylhydrazyl as reagent. A correlation between i.r. carbonyl ratio and the yield of peroxides has been established.     

Biological Potentials and Phytochemical Constituents of Raw and Roasted Nigella arvensis and Nigella sativa

Nigella species are widely used to cure various ailments. Their health benefits, particularly from the seed oils, could be attributed to the presence of a variety of bioactive components. Roasting is a critical process that has historically been used to facilitate oil extraction and enhance flavor; it may also alter the chemical composition and biological properties of the Nigella seed. The aim of this study was to investigate the effect of the roasting process on the composition of the bioactive components and the biological activities of Nigella arvensis and Nigella sativa seed extracts. Our preliminary study showed that seeds roasted at 50 °C exhibited potent antimicrobial activities; therefore, this temperature was selected for roasting Nigella seeds. For extraction, raw and roasted seed samples were macerated in methanol. The antimicrobial activities against Streptococcus agalactiae, Streptococcus epidermidis, Streptococcus pyogenes, Candida albicans, Escherichia coli, Enterobacter aerogenes, Klebsiella pneumoniae, and Klebsiella oxytoca were determined by measuring the diameter of the zone of inhibition. The cell viability of extracts was tested in a colon carcinoma cell line, HCT-116, by using a microculture tetrazolium technique (MTT) assay. Amino acids were extracted and quantified using an automatic amino acid analyzer. Then, gas chromatography–mass spectrometry (GC–MS) analysis was performed to identify the chemical constituents and fatty acids. As a result, the extracts of raw and roasted seeds in both Nigella species showed strong inhibition against Klebsiella oxytoca, and the raw seed extract of N. arvensis demonstrated moderate inhibition against S. pyogenes. The findings of the MTT assay indicated that all the extracts significantly decreased cancer cell viability. Moreover, N. sativa species possessed higher contents of the measured amino acids, except tyrosine, cystine, and methionine. The GC–MS analysis of extracts showed the presence of 22 and 13 compounds in raw and roasted N. arvensis, respectively, and 9 and 11 compounds in raw and roasted N. sativa, respectively. However, heat treatment decreased the detectable components to 13 compounds in roasted N. arvensis and increased them in roasted N. sativa. These findings indicate that N. arvensis and N. sativa could be potential sources of anticancer and antimicrobials, where the bioactive compounds play a pivotal role as functional components.     

α-Glucosidase, α-Amylase and Antioxidant Evaluations of Isolated Bioactives from Wild Strawberry

Diabetes mellitus is a metabolic disorder and is a global challenge to the current medicinal chemists and pharmacologists. This research has been designed to isolate and evaluate antidiabetic bioactives from Fragaria indica. The crude extracts, semi-purified and pure bioactives have been used in all in vitro assays. The in vitro α-glucosidase, α-amylase and DPPH free radical activities have been performed on all plant samples. The initial activities showed that ethyl acetate (Fi.EtAc) was the potent fraction in all the assays. This fraction was initially semi-purified to obtain Fi.EtAc 1–3. Among the semi-purified fractions, Fi.EtAc 2 was dominant, exhibiting potent IC₅₀ values in all the in vitro assays. Based on the potency and availability of materials, Fi.EtAc 2 was subjected to further purification to obtain compounds 1 (2,4-dichloro-6-hydroxy-3,5-dimethoxytoluene) and 2 (2-methyl-6-(4-methylphenyl)-2-hepten-4-one). The two isolated compounds were characterized by mass and NMR analyses. The compounds 1 and 2 showed excellent inhibitions against α-glucosidase (21.45 for 1 and 15.03 for 2 μg/mL), α-amylase (17.65 and 16.56 μg/mL) and DPPH free radicals (7.62 and 14.30 μg/mL). Our study provides baseline research for the antidiabetic bioactives exploration from Fragaria indica. The bioactive compounds can be evaluated in animals-based antidiabetic activity in future.     

Dapson in Heterocyclic Chemistry,Part I: Novel Synthesis of Sulfone Biscompounds for Antimicrobial and Antitumor Activities

This article describes the synthesis of some novel sulfone bis-compounds bearing the biologically active thioether 3–6 ; thioureido 7, 8, 15, 16; triazole 10, 11; thiosemicarbazido 9, 12, 13; and 1,3,4-thiadiazole 14, 17 moieties starting with 4,4′-diisothiocyanato-1,1-diphenylsulfone 2. The structures of newly synthesized compounds were confirmed by elemental analysis, IR, ¹ H-NMR and mass spectral data. Compound 3 was found to be the most active compound against Escherichia coli. Also, compound 15 acted as potent cytotoxic agent.     

Juncenolides H – K,New Briarane Diterpenoids from Junceella juncea

Chemical investigation of the Taiwanese gorgonian coral Junceella juncea resulted in the isolation of four new briarane‐type diterpenoids, juncenolides H, I, J, and K ( 1 – 4 ). Their structures were determined on the basis of spectroscopic analysis, especially 1‐ and 2D‐NMR. The inhibitory effects of compounds 1 – 4 on superoxide‐anion generation and elastase release by human neutrophils were evaluated.     

Distinct Mechanisms of Cytotoxicity in Novel Nitrogenous Heterocycles: Future Directions for a New Anti-Cancer Agent

Electron-rich, nitrogenous heteroaromatic compounds interact more with biological/cellular components than their non-nitrogenous counterparts. The strong intermolecular interactions with proteins, enzymes, and receptors confer significant biological and therapeutic properties to the imidazole derivatives, giving rise to a well-known and extensively used range of therapeutic drugs used for infections, inflammation, and cancer, to name a few. The current study investigates the anti-cancer properties of fourteen previously synthesized nitrogenous heterocycles, derivatives of imidazole and oxazolone, on a panel of cancer cell lines and, in addition, predicts the molecular interactions, pharmacokinetic and safety profiles of these compounds. Method: The MTT and CellTiter-Glo^® assays were used to screen the imidazole and oxazolone derivatives on six cancer cell lines: HL60, MDA-MB-321, KAIMRC1, KMIRC2, MCF-10A, and HCT8. Subsequently, in vitro tubulin staining and imaging were performed, and the level of apoptosis was measured using the Promega ApoTox-Glo^® triplex assay. Furthermore, several computational tools were utilized to investigate the pharmacokinetics and safety profile, including PASS Online, SEA Search, the QikProp tool, SwissADME, ProTox-II, and an in silico molecular docking study on tubulin to identify the critical molecular interactions. Results: In vitro analysis identified compounds 8 and 9 to possess the most significant potent cytotoxic activity on the HL60 and MDA-MB-231 cell lines, supported by PASS Online anti-cancer predictions with pa scores of 0.413 and 0.434, respectively. In addition, compound 9 induced caspase 3/7 dependent-apoptosis and interfered with tubulin polymerization in the MDA-MB-231 cell line, consistent with in silico docking results, identifying binding similarity to the native ligand colchicine. All the derivatives, including compounds 8 and 9, had acceptable pharmacokinetics; however, the safety profile was suboptimal for all the tested derivates except compound 4. Conclusion: The imidazole derivative compound 9 is a promising anti-cancer agent that switches on caspase-dependent apoptotic cell death and modulates microtubule function. Therefore, it could be a lead compound for further drug optimization and development.