Synthesis and reactions of [1]benzofuro[3,2-c]pyridine

(E)-3-(1-Benzofuran-2-yl)propenoic acid (I) was prepared from 1-benzofuran-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to [1]benzofuro[3,2-c]pyridin-1(2H)-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with zinc and acetic acid to the title compound V. [1]Benzofuro[3,2-c]pyridin-2-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. Treatment VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction) was shown to produce the corresponding [1]benzofuro[3,2-c]pyridin-1-carbonitrile (VII). The title compound was used for preparation of complex compounds VIII, IX

Potential application of bioactive compounds in essential oils from selected Malaysian herbs and spices as antifungal agents in food systems

Essential oils have a long history in their variety of applications. Although essential oils of various herbs and spices from other parts of the world have shown antimicrobial effects, those from Malaysian herbs remain underreported. Thus, can be further utilized in the search for novel bioactive compounds as natural antimicrobials to fulfil the consumers' demand for safer, healthier, and higher‐quality foods with longer shelf life. In the present work, the essential oils from ten herbs and spices namely betel, cinnamon, clove, coriander, galangal, ginger, lemongrass, lime, nutmeg, and turmeric, selected based on their abundance and economic importance, were analysed by gas chromatography and mass spectrometry. A total of 120 bioactive compounds were detected. The major (>10%) bioactive compounds were anethole, 26.25% (betel), cinnamaldehyde, 63.39% (cinnamon), eugenol, 87.16% (clove), linalool, 54.79% (coriander), propenoic acid, 29.56% (galangal), α-zingiberene, 26.32% (ginger), geranial, 42.61% (lemongrass), limonene, 39.84% (lime), β-phellandrene, 27.80% (nutmeg), and ar-turmerone, 41.81% (turmeric). All essential oils also yielded minor (<10%) bioactive compounds of different classes. Some of these major and minor bioactive compounds have been reported to exert fungicidal/fungistatic effects and could be an excellent candidate in the development of efficient fungal spoilage control strategies such as an active food packaging system.

SYNTHESIS OF A MODIFIED 4-AMINOBENZOIC ACID DERIVATIVE UNDER ULTRASOUND CONDITIONS

The search for new effective drugs with biologically active properties is one of the urgent problems. Recently, to intensify the process of their synthesis and increase the efficiency of chemical reactions, wave chemistry has been used. Increased interest of researchers is caused by the synthesis of compounds with biologically active properties using the method of ultrasonic treatment (US). It is known that derivatives of p-aminobenzoic acid and their esters are synthetic analogues of natural compounds, and pyrrolidone derivatives have high hypnotic, anticonvulsant, antiarrhythmic activity, which stimulates the synthesis of new biologically active compounds. In a brief report, the possibility of synthesizing ethyl-4-(2,5-dioxo-2,5-dihydro-1H-pyrrolyl) benzoate from 3-[(4-ethoxycarbonyl) phenylcarbamoyl]-2-propenoic acid using ultrasonic activation through a step is considered disclosure of the furan cycle with further cyclization. Ethyl ester p-aminobenzoic acid and maleic anhydride were used as starting reagents. An ultrasound device IL-100-6/2, equipped with a magnetostrictive transducer, with an operating frequency of 22 kHz, with a maximum power of 1200 W and a cylindrical waveguide, was used as a source of ultrasound. The synthesis of 3-[(4-ethoxycarbonyl) phenylcarbamoyl]-2-propenoic acid was carried out by reacting the starting reagents at equimolar ratios and room temperature. The US time was 10 minutes. The reaction proceeds smoothly. Ultrasound has a significant effect on the rate of chemical reactions and can increase the yield of the final product. Under classical conditions, the synthesis time was 180 minutes; using ultrasound, the synthesis time was reduced by 3 times. The product yield was 92%. The structure and composition of the obtained compound was confirmed by IR- and H1 NMR-spectroscopy. In the IR-spectra of the obtained compound, there are absorption bands of the amide group (NHCO) in the region of 3280, 3190 cm-1, absorption bands of the carbonyl group (C=O), characteristic in the region of 1670 cm-1, absorption band (COC) in the region of 1230 cm-1. The resulting compound, 3-[(4-Ethoxycarbonyl) phenylcarbamoyl]-2-propenoic acid, made it possible to study the step of opening the furan ring, with further cyclization. Ethyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrolyl) benzoate was obtained in 89% yield by azeotropic distillation of water in the presence of toluenesulfonic acid in a DMFA-toluene mixture. The resulting product is a light yellow powder with melting point 114-115°C. The structure and composition of the obtained compound was confirmed by IR-and H1 NMR-spectroscopy. In the IR-spectra of the obtained compound, the stretching vibrations of the НС=СН group manifest themselves in the form of a low-intensity but characteristic signal at 3100-3090 cm-1, stretching vibrations of the С=О group as intense bands in the region of 1700-1680 cm-1 and a weak overtone at 3465-3450 cm-1, stretching vibrations of the COC group in the region of 1245 cm-1. When analyzing the Н1 NMR-spectrum of a compound, ethyl 4-(2,5-dioxo-2,5-dihydro-1Н-pyrrolyl) benzoate, the signals of aromatic four protons Н1- Н2 (4Нaryl, 3JНН 8 Hz) are recorded in the field of weak fields: H1 doublet at 7.51 ppm. and a doublet at 8.05 ppm. Signals of the ethyl fragment: (3H, CH3, 3JHH 8 Hz), appear as a singlet at 1.43 ppm. and (2H, CH2, 3JHH 8 Hz) quadruplet at 4.34 ppm. The protons of the CH group of the imide cycle (2H, CH=CH) appear as a singlet at 7.11 ppm. Keywords: ultrasound, ethyl ether p-aminobenzoic acid, maleic anhydride, cyclization.

Tensile and transverse strength of novel copolymers for denture base.

Objectives: Compare tensile and transverse strength of new copolymers for denture base. Materials and methods: The specimens were prepared from heat cured acrylic resin with three types of additives: Acryester B, Ethoxycarbonylethylene, and Propenoic acid at a percentage of 5% and 10%. The tensile and transverse strains were tested, recorded and compared. Results: The analysis of variance display statistically significant difference. The p-value was 0.001 for each of tensile and transverse strain tests. Conclusions: The tensile strength of the novel copolymers increased. The transverse strength of some of the novel copolymers increased.

Chemical Constituents and Antidepressant-Like Effects in Ovariectomized Mice of the Ethanol Extract of Alternanthera philoxeroides

The previously unreported flavone glycoside, demethyltorosaflavone B (2) and the E-propenoic acid substituted flavone, torosaflavone E (3a), were isolated together with nine previously reported metabolites, including indole-3-carbaldehyde, oleanonic acid, vanillic acid, p-hydroxybenzoic acid, altheranthin (1a), alternanthin B (1b), demethyltorosaflavone D (3b), luteolin 8-C-E-propenoic acid (4) and chrysoeriol 7-O-rhamnoside (5), from the ethanol extract of the aerial part of Althernanthera philoxeroides. The crude ethanol extract was evaluated for its in vitro estrogenic activity in MCF-7 breast cancer cell line. The crude ethanol extract was also investigated in vivo for its antidepressant-like effects on ovariectomized mice using tail suspension and forced swimming tests, while its effect on the locomotor activity was evaluated by a Y-maze test. The effect of the crude extract on the serum corticosterone level, size and volume of uterus of the ovariectomized mice were also investigated. The expression of the mouse cyclic adenosine monophosphate (cAMP) response element-binding protein (CREB), brain-derived neurotrophic factor (BDNF) and β-actin mRNAs in hippocampus and frontal cortex was also evaluated, using semiquantitative reverse transcription-polymerase chain reaction. The crude extract and the isolated compounds 1a, 1b, 3a, 3b and 5, were evaluated for their inhibitory effects on monoamine oxidases (MAOs)-A and -B.

Simplicillium coffeanum, a new endophytic species from Brazilian coffee plants, emitting antimicrobial volatiles

During a bioprospecting of fungi producing antimicrobial volatile organic compounds, two Verticillium-like isolates from coffee branches were obtained by a parallel growth technique using Muscodor albus CZ 620. Micro-morphological characteristics and phylogenetic analyses showed that both isolates belonged to Simplicillium and represented a new species, namely S. coffeanum. In the test for antimicrobial activity, the mixture of volatiles emitted by S. coffeanum COAD 2057 inhibited the growth of Aspergillus ochraceus, A. tubingensis, A. sydowii and A. niger on PDA. Among the compounds of volatile mixture, 1-Propanone, 1-(5-methyl-2-furanyl)-, Cyclopropane, 1-ethoxy-2, 2-dimethyl-3-(2-phenylethynyl)-, and 2-Propenoic acid, 3-(2-formyl-4-methoxyphenyl)-, ethyl ester, (E)- possessed the highest percentage of peak per area. Therefore, S. coffeanum has potentially biocontrol ability through the emission of antimicrobial volatiles.