Zastosowanie spektroskopii UV w identyfikacji położenia podstawników w pierścieniu pirymidynowym

Pyrimidine is six-member heterocyclic compound that contains two nitrogen atoms at positions 1 and 3. Pyrimidine derivatives have showed various biological activities such as antimicrobial, antitumor, antifungal, the hypnotic and sedative activities. The oxopyrimidnes of the biological activity of the most possess substituents at the N1 or N3 position [1-11].This paper presents identification the location of the N1 and N3 isomeric substituents of the pyrimidine derivatives. The UV spectroscopy was used for this purpose. This method is simple, economical and does not require large quantities of sample.The absorption maxima of the 1 and 3-substituted pyrimidine derivatives were sensitive to the addition of base. In alkaline solution the N3-alkyl substituted uracil showed bathochromic shift, but the absorption maxima of N1 analogs shift toward shorter wavelengths (the hypsochromic shift) (Figure 1, 2, 3). This was associated with the formation of monoanion, which was created as a result of dissociation of a proton from the nitrogen atom (Scheme 2).The results were compared with the results that may be obtained from the analysis of proton nuclear magnetic resonance 1H NMR (Scheme 1, 3, 4). The NMR spectroscopy is a method much more precise and it can provide more information about the structure of the compound. By 1H NMR is not always possible clearly distinguish between N1 and N3 isomers, in contrast to the UV spectroscopy.Pirymidyna jest jednopierścieniowym, sześcioczło-nowym heterocyklicznym związkiem aromatycznym zawie-rającym dwa atomy azotu w pozycji 1 i 3. Jej pochodne zawierające podstawniki w pozycji N1 i N3 wykazują aktywność biologiczną i znajdują zastosowanie jako środki przeciwbakteryjne, przeciwgrzybicze, przeciwnowotworowe oraz uspokajające i nasenne [1-11].W pracy została przedstawiona identyfikacja położenia podstawników w izomerycznych N1 i N3 pochodnych pirymidynowych. Do tego celu wykorzystano prostą, ekonomiczną, niewymagającą dużych ilości próbki metodę – spektroskopię UV. Wykonane w środowisku zasadowym widma UV pochodnych N1 podstawionych pochodnych uracylu wykazują charakterystyczne przesunięcie hipsochro-mowe maksimum absorbancji w stosunku do widma wyko-nanego w pH = 7 (rys. 1, 2, 3). Efekt ten jest spowodowany powstawaniem monoanionu przez dysocjację protonu z azotu N3 (schemat 2). Natomiast dysocjacja protonu z azotu N1 w N3 podstawionych pochodnych uracylu prowadzi do powstania monoanionu z układem o znacznie silniejszym sprzężeniu (schemat 2). Wykonane w środowisku zasado-wym widma UV tych związków wykazują charakterystyczne przesunięcie maksimum absorbancji w kierunku dłuższych fal – efekt batochromowy (rys. 1, 2, 3).Uzyskane wyniki zostały porównane z wynikami analizy widma protonowego rezonansu jądrowego (1H NMR) (schemat 1, 3, 4). Spektroskopia NMR jest metodą znacznie bardziej dokładną. Można dzięki niej uzyskać więcej informacji o strukturze chemicznej badanego związku. Niestety, specyfika metody nie zawsze pozwala na rozróż-nienie izomerycznych pochodnych N1 i N3 pirymidyny. Natomiast analiza widma UV pozwala w każdym przypadku w sposób jednoznaczny określić położenie podstawnika w pierścieniu pirymidynowym

UV identification substitution position of pyrimidine ring

Pyrimidine is six-member heterocyclic compound that contains two nitrogen atoms at positions 1 and 3. Pyrimidine derivatives have showed various biological activities such as antimicrobial, antitumor, antifungal, the hypnotic and sedative activities. The oxopyrimidnes of the biological activity of the most possess substituents at the N 1 or N 3 position [1-11]. This paper presents identification the location of the N 1 and N 3 isomeric substituents of the pyrimidine derivatives. The UV spectroscopy was used for this purpose. This method is simple, economical and does not require large quantities of sample. The absorption maxima of the 1 and 3-substituted pyrimidine derivatives were sensitive to the addition of base. In alkaline solution the N 3-alkyl substituted uracil showed bathochromic shift, but the absorption maxima of N 1 analogs shift toward shorter wavelengths (the hypsochromic shift) (Figure 1, 2, 3). This was associated with the formation of monoanion, which was created as a result of dissociation of a proton from the nitrogen atom (Scheme 2). The results were compared with the results that may be obtained from the analysis of proton nuclear magnetic resonance 1 H NMR (Scheme 1, 3, 4). The NMR spectroscopy is a method much more precise and it can provide more information about the structure of the compound. By 1 H NMR is not always possible clearly distinguish between N 1 and N 3 isomers, in contrast to the UV spectroscopy.Pirymidyna jest jednopierścieniowym, sześcioczło-nowym heterocyklicznym związkiem aromatycznym zawie-rającym dwa atomy azotu w pozycji 1 i 3. Jej pochodne zawierające podstawniki w pozycji N 1 i N 3 wykazują aktywność biologiczną i znajdują zastosowanie jako środki przeciwbakteryjne, przeciwgrzybicze, przeciwnowotworowe oraz uspokajające i nasenne [1-11]. W pracy została przedstawiona identyfikacja położenia podstawników w izomerycznych N 1 i N 3 pochodnych pirymidynowych. Do tego celu wykorzystano prostą, ekonomiczną, niewymagającą dużych ilości próbki metodę – spektroskopię UV. Wykonane w środowisku zasadowym widma UV pochodnych N 1 podstawionych pochodnych uracylu wykazują charakterystyczne przesunięcie hipsochro-mowe maksimum absorbancji w stosunku do widma wyko-nanego w pH = 7 (rys. 1, 2, 3). Efekt ten jest spowodowany powstawaniem monoanionu przez dysocjację protonu z azotu N 3 (schemat 2). Natomiast dysocjacja protonu z azotu N 1 w N 3 podstawionych pochodnych uracylu prowadzi do powstania monoanionu z układem o znacznie silniejszym sprzężeniu (schemat 2). Wykonane w środowisku zasado-wym widma UV tych związków wykazują charakterystyczne przesunięcie maksimum absorbancji w kierunku dłuższych fal – efekt batochromowy (rys. 1, 2, 3). Uzyskane wyniki zostały porównane z wynikami analizy widma protonowego rezonansu jądrowego ( 1 H NMR) (schemat 1, 3, 4). Spektroskopia NMR jest metodą znacznie bardziej dokładną. Można dzięki niej uzyskać więcej informacji o strukturze chemicznej badanego związku. Niestety, specyfika metody nie zawsze pozwala na rozróż-nienie izomerycznych pochodnych N 1 i N 3 pirymidyny. Natomiast analiza widma UV pozwala w każdym przypadku w sposób jednoznaczny określić położenie podstawnika w pierścieniu pirymidynowym

Multi-functionality of the few: Current and past uses of wild plants for food and healing in LiubaÅ\u84 region, Belarus

Background: This study examined the use of wild plants in the food, medicinal and veterinary areas within a small territory limited to one village council in the LiubaÅ\u84 district of Belarus. The objectives of the research were to document the current and past uses of wild plants in this region for food and human/animal medication; to analyse the food, medicinal and veterinary areas in the context of wild plants; and to qualitatively compare the results with relevant publications concerning the wild food plants of Belarus. Methods: Fieldwork was carried out as a practical part of a development cooperation project in May 2016 in 11 villages of the LiubaÅ\u84 district. One hundred thirty-four respondents were selected randomly. Information about local uses of wild plants was obtained via semi-structured interviews and the folk-history method. Interview records were digitalized and the data structured in Detailed Use Records (DUR), which were divided into food, medicinal and veterinary areas and then analysed to ascertain local perceptions. Results: A total of 2252 DUR of wild plants were recorded. Eighty-eight wild plant taxa belonging to 45 plant families were used across all three areas. Of these, 58 taxa were used in the food, 74 in the medicinal and 23 in the veterinary areas. A relatively high percentage of the taxa were used in both the food and medicinal areas (55%) and an even greater percentage in both the medicinal and veterinary areas (87%). Comparison with earlier research on wild food plants shows the considerable difference among seldom-mentioned taxa or uses, showing possible regional differences despite the homogenization of the population during the Soviet era. Conclusions: As the majority of taxa with overlapping uses belonged to the most utilized plants, there appears to be clear a tendency to use plants in several different areas once they are brought into the home. This may be due to the need to maximize the versatility of limited resources. While the number of wild taxa used is relatively high, the mean number of taxa used per person is quite low, which indicates the relatively minor importance of wild plants in the respective areas in the study region. The low importance of snacks signals that unintended contact with nature has been lost

Enantioselective Bioreduction of Prochiral Pyrimidine Base Derivatives by Boni Protect Fungicide Containing Live Cells of Aureobasidium pullulans

The enzymatic enantioselective bioreduction of prochiral 1-substituted-5-methyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-diones to corresponding chiral alcohols by Boni Protect fungicide containing live cells of Aureobasidium pullulans was studied. The microbe-catalyzed reduction of bulky-bulky ketones provides enantiomerically pure products (96–99% ee). In the presence of A. pullulans (Aureobasidium pullulans), one of the enantiotopic hydrides of the dihydropyridine ring coenzyme is selectively transferred to the si sides of the prochiral carbonyl group to give secondary alcohols with R configuration. The reactions were performed under various conditions in order to optimize the procedure with respect to time, solvent, and temperature. The present methodology demonstrates an alternative green way for the synthesis of chiral alcohols in a simple, economical, and eco-friendly biotransformation

Novel 2-(Adamantan-1-ylamino)Thiazol-4(5H)-One Derivatives and Their Inhibitory Activity towards 11β-HSD1—Synthesis, Molecular Docking and In Vitro Studies

A common mechanism in which glucocorticoids participate is suggested in the pathogenesis of such metabolic diseases as obesity, metabolic syndrome, or Cushing’s syndrome. The enzyme involved in the control of the availability of cortisol, the active form of the glucocorticoid for the glucocorticoid receptor, is 11β-HSD1. Inhibition of 11β-HSD1 activity may bring beneficial results for the alleviation of the course of metabolic diseases such as metabolic syndrome, Cushing’s syndrome or type 2 diabetes. In this work, we obtained 10 novel 2-(adamantan-1-ylamino)thiazol-4(5H)-one derivatives containing different substituents at C-5 of thiazole ring and tested their activity towards inhibition of two 11β-HSD isoforms. For most of them, over 50% inhibition of 11β-HSD1 and less than 45% inhibition of 11β-HSD2 activity at the concentration of 10 µM was observed. The binding energies found during docking simulations for 11β-HSD1 correctly reproduced the experimental IC50 values for analyzed compounds. The most active compound 2-(adamantan-1-ylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one (3i) inhibits the activity of isoform 1 by 82.82%. This value is comparable to the known inhibitor-carbenoxolone. The IC50 value is twice the value determined by us for carbenoxolone, however inhibition of the enzyme isoform 2 to a lesser extent makes it an excellent material for further tests

11β-Hydroxysteroid Dehydrogenase Type 1 as a Potential Treatment Target in Cardiovascular Diseases

Glucocorticoids (GCs) belong to the group of steroid hormones. Their representative in humans is cortisol. GCs are involved in most physiological processes of the body and play a significant role in important biological processes, including reproduction, growth, immune responses, metabolism, maintenance of water and electrolyte balance, functioning of the central nervous system and the cardiovascular system. The availability of cortisol to the glucocorticoid receptor is locally controlled by the enzyme 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). Evidence of changes in intracellular GC metabolism in the pathogenesis of obesity, metabolic syndrome (MetS) and cardiovascular complications highlights the role of selective 11β-HSD1 inhibition in the pharmacotherapy of these diseases. This paper discusses the role of 11β-HSD1 in MetS and its cardiovascular complications and the importance of selective inhibition of 11β-HSD1

Microbial Synthesis of (S)- and (R)-Benzoin in Enantioselective Desymmetrization and Deracemization Catalyzed by Aureobasidium pullulans Included in the Blossom Protect™ Agent

In this study, we examined the Aureobasidium pullulans strains DSM 14940 and DSM 14941 included in the Blossom Protect™ agent to be used in the bioreduction reaction of a symmetrical dicarbonyl compound. Both chiral 2-hydroxy-1,2-diphenylethanone antipodes were obtained with a high enantiomeric purity. Mild conditions (phosphate buffer [pH 7.0, 7.2], 30 °C) were successfully employed in the synthesis of (S)-benzoin using two different methodologies: benzyl desymmetrization and rac-benzoin deracemization. Bioreduction carried out with higher reagent concentrations, lower pH values and prolonged reaction time, and in the presence of additives, enabled enrichment of the reaction mixture with (R)-benzoin. The described procedure is a potentially useful tool in the synthesis of chiral building blocks with a defined configuration in a simple and economical process with a lower environmental impact, enabling one-pot biotransformation

The effectiveness of natural and synthetic immunomodulators in the treatment of inflammatory bowel disease in dogs

The aim of the study was to evaluate the usefulness of immunomodulators in the treatment of inflammatory bowel disease (IBD) in dogs. Twenty-eight dogs diagnosed with IBD took part in the study. The animals received a food containing extruded immunomodulators: β-1,3/1,6-D-glucan, β-hydroxy-β-methyl-butyrate (HMB) and levamisole for 42 days. Whole blood samples were analysed before and after therapy assessing changes in phagocyte activity (respiratory burst activity, RBA and potential killing activity, PKA), evaluation of proliferation response of mitogen-stimulated lymphocytes and serum gamma globulin levels, lysozyme activity, ceruloplasmin levels and interleukin activity (IL-6 and IL-10). In this experiment, β-1,3/1,6-D-glucan delivered the highest level of treatment efficacy by producing the quickest therapeutic effect, lowering Canine Inflammatory Bowel Disease Activity Index (CIBDAI) values to below 3, improving histopathological parameters, decreasing IL-6 levels, increasing IL-10 concentrations, and producing remission periods longer than six months. HMB and levamisole were also effective in lowering CIBDAI scores, but the abatement of clinical symptoms was slower and less pronounced in comparison with β-1,3/1,6-D-glucan. The results indicate that β-1,3/1,6-D-glucan can be useful in the treatment of canine IBD