Synthesis, Absolute Configuration, Biological Profile and Antiproliferative Activity of New 3,5-Disubstituted Hydantoins.

Hydantoins, a class of five-membered heterocyclic compounds, exhibit diverse biological activities. The aim of this study was to synthesize and characterize a series of novel 3,5-disubstituted hydantoins and to investigate their antiproliferative activity against human cancer cell lines. The new hydantoin derivatives - were prepared as racemic mixtures of - and -isomers via a base-assisted intramolecular amidolysis of C-3 functionalized β-lactams.

A multimodal treatment of basilar artery re-occlusion - case report.

Background: Stroke due to basilar artery occlusion (BAO) is a severe neurovascular condition with only recently proven effectiveness of mechanical thrombectomy as treatment. Early re-occlusion of the basilar artery (RE-BAO) is an even more challenging form of stroke to treat, associated with poor outcomes and still no optimal treatment guidelines. There are only a few reported cases covering this topic thus far.

Total Synthesis and Biological Profiling of Putative (±)-Marinoaziridine B and (±)--Methyl Marinoaziridine A.

The total synthesis of two new marine natural products, (±)-marinoaziridine B and (±)--methyl marinoaziridine A , was accomplished. The (±)-marinoaziridine was prepared in a six-step linear sequence with a 2% overall yield. The key steps in our strategy were the preparation of the chiral epoxide (±)- using the Johnson Corey Chaykovsky reaction, followed by the ring-opening reaction and the Staudinger reaction.

New Levan-Based Chiral Stationary Phases: Synthesis and Comparative HPLC Enantioseparation of (±)--β-Lactam Ureas in the Polar Organic Mode.

In this paper, the preparation of three new polysaccharide-type chiral stationary phases (CSPs) based on levan carbamates (3,5-dimethylphenyl, 4-methylphenyl, and 1-naphthyl) is described. The enantioseparation of (±)--β-lactam ureas - was investigated by high-performance liquid chromatography (HPLC) on six different chiral columns (Chiralpak AD-3, Chiralcel OD-3, Chirallica PST-7, Chirallica PST-8, Chirallica PST-9, and Chirallica PST-10) in the polar organic mode, using pure methanol (MeOH), ethanol (EtOH), and acetonitrile (ACN). Apart from the Chirallica PST-9 column (based on levan (1-naphthylcarbamate), the columns exhibited a satisfactory chiral recognition ability for the tested -β-lactam ureas -.

Novel (±)---lactam ureas: Synthesis, and biological profiling.

A diastereomeric mixture of racemic 3-phthalimido--lactam / was synthesized by the Staudinger reaction of carboxylic acid activated with 2-chloro-1-methylpyridinium iodide and imine . The amino group at the C3 position of the -lactam ring was used for further structural upgrade. --lactam ureas were prepared by the condensation reaction of the amino group of -lactam ring with various aromatic and aliphatic isocyanates.

Bioprospecting of Five sp. Cultivars from Croatia: New Potential for Dietary and Dermatological Application with Embryotoxicity Tests.

L. is the most common species, and it is used as an ornamental plant and in food condiments. This unique study examined the chemical composition and biological activities of six extracts from five basil cultivars, including their antimicrobial, antidiabetic, antilipidemic, neuroprotective, and anticollagenase activity.

Physicochemical Properties, Antioxidant Capacity, and Bioavailability of L. Leaf Polyphenolic Extracts Microencapsulated by Spray Drying.

Laurel ( L.) leaves are a rich source of polyphenols with the potential for use in functional foods, where the main obstacle is their low stability and bioavailability, which can be improved by spray drying (SD). This research examined the influence of SD parameters, including inlet temperature (120, 150, and 180 °C), carrier type (β-cyclodextrin (β-CD); β-CD + maltodextrin (MD) 50:50; β-CD + gum arabic (GA) 50:50), and sample:carrier ratio (1:1, 1:2 and 1:3) on the physicochemical properties, encapsulation efficiency, polyphenolic profile, antioxidant capacity and bioaccessibility of laurel leaf polyphenols.

Effect of Spray Drying Encapsulation on Nettle Leaf Extract Powder Properties, Polyphenols and Their Bioavailability.

Nettle ( L.) is a plant rich in a health-promoting compounds such as polyphenols, which are sensitive and unstable compounds with low bioavailability, that need to be stabilized and protected from external influences. Therefore, the aim of this study was to examine how the temperature, type of carrier and sample to carrier ratio influence the physicochemical properties and encapsulation and loading capacity of the nettle leaf extract powder and examine the effect of encapsulation on the antioxidant capacity and bioavailability of polyphenols.

Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides.

Enantioseparation of the newly synthesized series of novel quinoline-2(1)-one epoxide structures -- and --, named marinoepoxides, is described. Marinoepoxide -, the key intermediate in the total synthesis of natural products marinoaziridines A and B, as well as their structural analogues, was synthesized by addition of the achiral ylide generated in situ from the sulfonium salt or , to the carbon-oxygen double bond of the corresponding quinoline-2(1)-one-4-carbaldehyde - in good yield. Separation of enantiomers of (±)-2,3,3-trisubstituted marinoepoxides -- and (±)--2,3-disubstituted marinoepoxides -- was studied using two immobilized polysaccharide type chiral stationary phases (CSPs); -(3,5-dichlorophenylcarbamoyl)cellulose stationary phase (CHIRAL ART Cellulose-SC) and (3,5-dimethylphenylcarbamoyl)amylose stationary phase (CHIRAL ART Amylose-SA).

Polyphenol Composition, Anticholinesterase and Antioxidant Potential of the Extracts of Clinopodium vulgare L.

Clinopidium vulgare L. (wild basil, Lamiaceae) is a well-known medicinal plant used in the traditional medicine in many countries. Medicinal plants present potential sources of bioactive compounds.

Microwave Assisted Extraction and Pressurized Liquid Extraction of Sulfated Polysaccharides from and .

Sulfated polysaccharide fucoidan isolated from brown algae shows a wide range of biological activities that are significantly dependent on its chemical composition, which is closely related to the applied technique and extraction parameters. Therefore, the objective of this study was to evaluate the influence of microwave assisted extraction (MAE) and pressurized liquid extraction (PLE) parameters (solvent, temperature, time, and number of cycles) on the and polysaccharide yield (%PS) and chemical composition (total sugar, fucose, and sulfate group). The optimal MAE parameters that resulted in the highest polysaccharide extraction from and were 0.

Investigation of the glucosinolates in Hesperis matronalis L. and Hesperis laciniata All.: Unveiling 4'-O-β-d-apiofuranosylglucomatronalin.

The glucosinolate (GSL) profiles of wild-growing plants from the genus Hesperis, i.e. Hesperis laciniata All.

Chemical Diversity of Headspace and Volatile Oil Composition of Two Brown Algae ( and ) from the Adriatic Sea.

Two selected brown algae ( and from the family Dictyotaceae, order Dictyotales) growing in the same area (island Vis, central Adriatic Sea) were collected at the same time. Their phytochemical composition of the headspace volatile organic compounds (HS-VOCs; first time report) was determined by headspace solid-phase microextraction (HS-SPME). Hydrodistillation was applied for the isolation of their volatile oils (first report on volatile oil).

Green asymmetric reduction of acetophenone derivatives: Saccharomyces cerevisiae and aqueous natural deep eutectic solvent.

Objective: Chiral building blocks [(S)-1-(3-methylphenyl)ethanol, (S)-1-(3,4-dimethylphenyl)ethanol and (S)-1-(2,4,6-trimethylphenyl)ethanol] for drug synthesis were prepared using two green approaches: (1) the yeast Saccharomyces cerevisiae as the biocatalyst and (2) the natural deep eutectic solvents (NADES) as the alternative solvents. Three different NADES with different water contents were prepared and screened for the highest conversion and enantiomeric excess of reduction of 1-(3-methylphenyl)ethanone, 1-(3,4-dimethylphenyl)ethanone (DMPA) and 1-(2,4,6-trimethyphenyl)ethanone by S. cerevisiae.

Phytochemical Composition, Antioxidant Potential and Cholinesterase Inhibition Potential of Extracts from Mentha pulegium L.

The aim of this work was to perform the phytochemical analysis as well as antioxidant and anticholinesterase potential of hot water and methanolic extracts from Mentha pulegium L., Lamiaceae, wild growing in Bosnia and Herzegovina. It is a plant that is traditionally used in Bosnia and Herzegovina medicine to treat gastrointestinal and neurological disorders.

Phytochemical study of the headspace volatile organic compounds of fresh algae and seagrass from the Adriatic Sea (single point collection).

Performed phytochemical study contributes to the knowledge of volatile organic compounds (VOCs) of Halopteris filicina (Grateloup) Kützing, Dictyota dichotoma (Hudson) J. V. Lamouroux, Posidonia oceanica (L.

Phytochemical Composition and Antioxidant Activities of the Essential Oil and Extracts of Satureja subspicata Vis. Growing in Bosnia and Herzegovina.

The phytochemical composition and the antioxidant activities of the essential oil, as well as methanol and hot water extracts of endemic Satureja subspicata Vis. growing in Bosnia and Herzegovina (BiH), were described. β-Caryophyllene, cis-β-ocimene, and α-pinene, identified by GC/MS and GC-FID, were the dominant oil components.

GC-FID/MS Profiling of Supercritical CO2 Extracts of Peels from Citrus aurantium, C. sinensis cv. Washington navel, C. sinensis cv. Tarocco and C. sinensis cv. Doppio Sanguigno from Dubrovnik Area (Croatia).

The peels of Citrus aurantium L. and Citrus sinensis Osbeck cultivars from the Dubrovnik region (south Croatia) were extracted by supercritical CO2 at 40 degrees C and 10 MPa at 1.76 kg/h to obtain enriched extracts in comparison with simple pressing of the peels.

Bioorganic research of Galactites tomentosa Moench. Honey extracts: enantiomeric purity of chiral marker 3-phenyllactic acid.

Thistle (Galactites tomentosa Moench.) honey organic extracts were obtained by headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE) and analyzed by gas chromatography (GC-FID and GC-MS) for the first time. Most abundant headspace compounds were terpenes, particularly linalool derivatives (hotrienol was predominant with a range of 38.

Chemical profile of the organic residue from ancient amphora found in the Adriatic Sea determined by direct GC and GC-MS analysis.

An ancient organic residue was collected from the bottom of a Greco-Italian amphora found in the Adriatic Sea and investigated by direct GC and GC-MS analysis. The headspace composition was determined by HS-SPME using: (1) DVB/CAR/PDMS and (2) PDMS/DVB fibres. Higher percentages of benzene derivatives, monoterpenes and other low-molecular aliphatic compounds were obtained by method (1) in contrast to higher percentage of naphthalene and phenanthrene derivatives found by method (2).

CD-sensitive Zn-porphyrin tweezer host-guest complexes, part 2: cis- and trans-3-hydroxy-4-aryl/alkyl-beta-lactams. A case study.

This article describes an application of the host-guest chiral recognition approach called tweezer methodology for the determination of the absolute configuration of 3-hydroxy-beta-lactams. These substrates represent challenging cases due to their chemical reactivity, the presence of multiple stereogenic centers and several functional groups which offer various possibilities of binding to the Zn-porphyrin host. OPLS-2005, the force field used in this work to predict the interporphyrin twist, modeled correctly the host-guest complexation mechanism and revealed conformational details of the bound substrates.

Determination of the absolute configuration of flexible molecules by ab initio ORD calculations: a case study with cytoxazones and isocytoxazones.

Ab initio calculations of the optical rotatory power of the natural cytokine modulator cytoxazone 1 and its trans-diastereomer 2, as well as the structural isomers cis-3 and trans-4 isocytoxazones, have been performed at four different wavelengths (589, 546, 435, and 405 nm) by Density Functional Theory. The calculation of ORD curves provides a reliable method for the assignment of absolute configuration of these conformationally flexible molecules. The absolute configurations of isocytoxazones has been established as (+)-(4R,5S)-cis-3 and (+)-(4S,5S)-trans-4.

Two-step asymmetric synthesis of disubstituted N-tosyl aziridines having 98-100% ee: use of a phosphazene base.

Unknown diaryl (1-3) and alkyl-phenyl (4, 5) N-tosyl aziridines have been successfully synthesized from pure (R,R,R,S(S))-(-)-sulfonium salt derived from Eliel's oxathiane, tosylimines 11a-f, and using a phosphazene base (EtP(2)) to generate the ylide. Both cis and trans aziridines have exceptionally high enantiomeric purities (98.7-99.

Trans-diaryl epoxides: asymmetric synthesis, ring-opening, and absolute configuration.

Anthryl-phenyl, phenanthryl-phenyl, and naphthyl-phenyl trans-epoxides (1, 2, and 3, respectively) having enantiomeric purities of 95%, 99%, and 96% were synthesized from a diastereo and enantiopure sulfonium salt derived from Eliel's oxathiane. The determination of their (1R,2R) absolute configurations was achieved by application of the CD exciton chirality method using a Zn-porphyrin tweezer on the corresponding alcohols obtained after opening of these epoxides with LiAlH(4). The R-configuration at C2 of these epoxides, (-)-1, (+)-2, and (-)-3, is consistent with our previous results concerning asymmetric synthesis of monoaryl epoxides, cyclopropanes, and aziridines.

erythro-1-Naphthyl-1-(2-piperidyl)methanol: synthesis, resolution, NMR relative configuration, and VCD absolute configuration.

The erythro isomer of 1-naphthyl-1-(2-piperidyl)methanol 4, an efficient chiral modifier for asymmetric heterogeneous hydrogenation, was obtained as the major isomer (95%) in two steps while the threo isomer can be obtained as the major isomer (67%) in three steps. erythro-4 and threo-4 were resolved on a CHIRALCEL OD-RH column. It has been shown by VCD that the diastereomer determined as the erythro by NMR was indeed the erythro and that the first eluted (-)-enantiomer on CHIRALCEL OD-R or -RH columns has the (1R,2S) configuration.