Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2017-11-28DOI: 10.1007/s00706-017-2083-9
Volkmar Trommer, Fabian Fischer, Marko Hapke
{"title":"Novel naphthylpyridines from cobalt-catalyzed cyclotrimerization of a chiral diyne.","authors":"Volkmar Trommer, Fabian Fischer, Marko Hapke","doi":"10.1007/s00706-017-2083-9","DOIUrl":"https://doi.org/10.1007/s00706-017-2083-9","url":null,"abstract":"<p><strong>Abstract: </strong>The concise synthesis of a novel chiral diyne substrate for the assembly of chiral naphthylpyridines was described and different conditions for the cobalt-catalyzed co-cyclotrimerization with nitriles investigated. The products are novel naphthylpyridines possessing configurationally stable biaryl axes.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"755-763"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2083-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031582","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Palladium complexes containing imino phenoxide ligands: synthesis, luminescence, and their use as catalysts for the ring-opening polymerization of <i>rac</i>-lactide.","authors":"Mrinmay Mandal, Manuela List, Ian Teasdale, Günther Redhammer, Debashis Chakraborty, Uwe Monkowius","doi":"10.1007/s00706-017-2119-1","DOIUrl":"10.1007/s00706-017-2119-1","url":null,"abstract":"<p><strong>Abstract: </strong>The preparation, structural characterization, luminescence, and catalytic activity of three palladium(II) complexes bearing imino phenoxide ligands are reported. The X-ray studies revealed that the complexes are mononuclear with palladium centres coordinated in a square-planar coordination environment. Two of the complexes are emissive in solution at room temperature. The catalytic activities towards the ring-opening polymerization of <i>rac</i>-lactide (<i>rac</i>-LA) were tested. Polymers with moderate molecular weights and relatively broad dispersity (<i>Ð</i>) were obtained. Kinetic studies revealed that the polymerization followed first-order kinetics.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"783-790"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906497/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031584","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2018-06-27DOI: 10.1007/s00706-018-2197-8
Renata Paprocka, Małgorzata Wiese-Szadkowska, Anna Helmin-Basa, Liliana Mazur, Jolanta Kutkowska, Jacek Michałkiewicz, Bożena Modzelewska-Banachiewicz, Leszek Pazderski
{"title":"Synthesis and evaluation of new amidrazone-derived hydrazides as a potential anti-inflammatory agents.","authors":"Renata Paprocka, Małgorzata Wiese-Szadkowska, Anna Helmin-Basa, Liliana Mazur, Jolanta Kutkowska, Jacek Michałkiewicz, Bożena Modzelewska-Banachiewicz, Leszek Pazderski","doi":"10.1007/s00706-018-2197-8","DOIUrl":"10.1007/s00706-018-2197-8","url":null,"abstract":"<p><strong>Abstract: </strong>The series of new hydrazide derivatives were synthesized in reactions of N<sup>3</sup>-substituted amidrazones with cyclic anhydrides as potential anti-inflammatory and antibacterial agents. The compounds were characterized by <sup>1</sup>H-<sup>13</sup>C two-dimensional NMR techniques, which revealed the presence of two tautomeric forms in DMSO-<i>d</i><sub>6</sub> solutions, while the molecular structure of one species was confirmed by single-crystal X-ray diffraction. The anti-inflammatory effects of hydrazides on peripheral blood mononuclear cells were experimentally evaluated. Three compounds showed antiproliferative activity comparable to ibuprofen. One derivative demonstrated strong reduction of lymphocyte proliferation stimulated by anti-CD3 antibody (by 90%) and PHA, as well as low cell toxicity. The obtained compounds exhibited relatively weak antibacterial activity; they were more effective against Gram-positive bacterial strains.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 8","pages":"1493-1500"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6060958/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36389687","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2018-07-13DOI: 10.1007/s00706-018-2251-6
Aneta Pogorzelska, Beata Żołnowska, Jarosław Sławiński, Anna Kawiak, Krzysztof Szafrański, Mariusz Belka, Tomasz Bączek
{"title":"Synthesis of 2-alkylthio-<i>N</i>-(quinazolin-2-yl)benzenesulfonamide derivatives: anticancer activity, QSAR studies, and metabolic stability.","authors":"Aneta Pogorzelska, Beata Żołnowska, Jarosław Sławiński, Anna Kawiak, Krzysztof Szafrański, Mariusz Belka, Tomasz Bączek","doi":"10.1007/s00706-018-2251-6","DOIUrl":"https://doi.org/10.1007/s00706-018-2251-6","url":null,"abstract":"<p><strong>Abstract: </strong>A new series of 2-alkylthio-<i>N</i>-(quinazolin-2-yl)benzenesulfonamide derivatives have been synthesized and evaluated in vitro for their antiproliferative activity by MTT assay against cancer cell lines HCT-116, MCF-7, and HeLa as well as the NCI-60 human tumor cell lines screen. In NCI screen, three compounds inhibited approximately 50% growth of RPMI-8226 and A549/ATCC cell lines. The mean of IC<sub>50</sub> calculated in MTT assays for three tested cell lines was about 45 μM for four compounds. The QSAR allowed finding statistically significant OPLS models for HeLa cell line. Metabolic stability in vitro studies indicated favorable and unfavorable structural elements. The good metabolic stability, with <i>t</i><sub>1/2</sub> higher than 40 min, was observed for three derivatives, which together with their antiproliferative activity and good ADMET profile, makes them good leading structures for further research.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 10","pages":"1885-1898"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2251-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36510811","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2018-02-03DOI: 10.1007/s00706-017-2085-7
Max Schmallegger, Georg Gescheidt
{"title":"Benzil/triethylamine: a photo-reducing system for Cu<sup>2</sup>.","authors":"Max Schmallegger, Georg Gescheidt","doi":"10.1007/s00706-017-2085-7","DOIUrl":"https://doi.org/10.1007/s00706-017-2085-7","url":null,"abstract":"<p><strong>Abstract: </strong>We have investigated the photo-induced reduction of Cu<sup>2+</sup>-Cu<sup>0</sup> using benzil/triethylamine mixtures. The formation of elemental Cu is indicated by the appearance of its characteristic plasmon absorption peaks at 515 nm and 620 nm. Importantly, the nature of the counterion of the Cu<sup>2+</sup> salt affects the reduction process. In the presence of Cl<sup>-</sup>, the reduction proceeds faster than with SO<sub>4</sub><sup>2-</sup>. Photo-induced electron transfer between excited benzil and triethylamine leads to the benzil radical anion, which acts as the reducing agent for Cu<sup>2+</sup> and generates Cu<sup>0</sup>.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 3","pages":"499-504"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2085-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35944695","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2017-11-29DOI: 10.1007/s00706-017-2114-6
Michael Haas, Sabrina Gonglach, Stefan Müllegger, Wolfgang Schöfberger
{"title":"Synthesis and characterization of <i>meso</i>-substituted A<sub>2</sub>B corroles with extended π-electronic structure.","authors":"Michael Haas, Sabrina Gonglach, Stefan Müllegger, Wolfgang Schöfberger","doi":"10.1007/s00706-017-2114-6","DOIUrl":"10.1007/s00706-017-2114-6","url":null,"abstract":"<p><strong>Abstract: </strong>We report the chemical synthesis and characterization of the stable 5,15-bis(pentafluorophenyl)-10-(trimethylsilylethynyl)corrole which serves as a precursor for the subsequent in situ sila-Sonogashira-cross-coupling reaction and metalation with copper(II) acetate. Under ambient conditions and a common catalyst system the reaction with 1-iodopyrene occurred within five hours. Due to the direct conjugation of the 18π-electronic system of the corrole macrocycle over the alkynyl group to the pyrene moiety the optical transitions in the Soret (B-) band Q-band region are significantly altered. The copper corrole exhibited complex hyperfine and superhyperfine structure in the EPR spectrum. The assignment of the EPR spectrum reveals the existence of an axial [CuII-cor<sup>∙+</sup>] species.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"773-781"},"PeriodicalIF":1.7,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906495/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031583","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2018-06-28DOI: 10.1007/s00706-018-2183-1
Dorota Gugała-Fekner
{"title":"Adsorption of adenine on mercury electrode in acetate buffer at pH 5 and pH 6 and its effect on electroreduction of zinc ions.","authors":"Dorota Gugała-Fekner","doi":"10.1007/s00706-018-2183-1","DOIUrl":"10.1007/s00706-018-2183-1","url":null,"abstract":"<p><strong>Abstract: </strong>The measurements of double-layer differential capacitance, zero charge potential, and surface tension at that potential allowed us to examine the adsorption properties of adenine on the mercury surface from the neat buffer solution, i.e., the acetate buffer at pH 5 and pH 6. The systems obtained at such pH values were close to physiological fluids in their characteristics. The adsorption energy and interaction constants were determined using Frumkin isotherm and virial isotherm. It was shown that the adenine molecule is adsorbed on the mercury electrode with its negative pole against the electrode surface. Using the cyclic voltammetry technique and measuring Faraday impedance, an increasing effect of adenine on the kinetics of zinc ion electroreduction was found. In both buffer solutions, the neutral adenine molecules can form on the surface of the working electrode, an unstable active complex with depolarizer ions, facilitating electron exchange.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 8","pages":"1357-1365"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6060954/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36391216","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2017-11-27DOI: 10.1007/s00706-017-2075-9
Esther Theresa Knittl, Azza A Abou-Hussein, Wolfgang Linert
{"title":"Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine.","authors":"Esther Theresa Knittl, Azza A Abou-Hussein, Wolfgang Linert","doi":"10.1007/s00706-017-2075-9","DOIUrl":"10.1007/s00706-017-2075-9","url":null,"abstract":"<p><strong>Abstract: </strong>A hydrazone Schiff base ligand was synthesized by the condensation of 3-formyl-4-hydroxycoumarin and oxalyldihydrazide in the molar ratio 2:1. The Schiff base ligand acts as a mono-, bi-, tri- or even tetradentate ligand with metal cations in the molar ratios 1:1 or 2:1 (<i>M</i>:<i>L</i>) to yield either mono- or binuclear complexes as keto or enol isomers, where <i>M</i> = Co(II), Ni(II), Cu(II), VO(IV), and Fe(III). The ligand and its metal complexes were characterized by elemental analyses, IR, <sup>1</sup>H NMR, mass, and UV-Vis spectroscopy. Furthermore, the magnetic moments were calculated from the measured electric conductivities of the complexes. According to the received data, the dihydrazone ligand contains one or two units of ONO domains and can bind to the metal ions via the azomethine nitrogen, the carbonyl oxygen atoms, and/or the phenolic oxygen atoms. Electronic spectra and the magnetic moments of all complexes show that the complexes' geometries are either octahedral, tetrahedral, square planar, or square pyramidal. Cyclic voltammograms of the mononuclear Co(II) and Ni(II) complexes show quasi-reversible peaks. Tests against two pathogenic bacteria as Gram-positive and Gram-negative bacteria for both, the Schiff base ligand and its metal complexes were carried out. In addition, also one kind of fungi was tested. The synthesized complexes demonstrate mild antibacterial and antifungal activities against these organisms.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 2","pages":"431-443"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5818636/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35876774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2018-03-03DOI: 10.1007/s00706-018-2176-0
Dorota Wójcik-Pastuszka, Anna M Biedrawa, Dorota Haznar-Garbacz, Witold S Musiał
{"title":"The influence of physical division of tablets on the variability of release kinetics of gliclazide.","authors":"Dorota Wójcik-Pastuszka, Anna M Biedrawa, Dorota Haznar-Garbacz, Witold S Musiał","doi":"10.1007/s00706-018-2176-0","DOIUrl":"https://doi.org/10.1007/s00706-018-2176-0","url":null,"abstract":"<p><strong>Abstract: </strong>Tablets are often used in splitting process when the appropriated, registered dose is not available on the market or patients exhibit swallowing difficulties caused by the size of the tablet. The aim of the work was to assess the impact of physical division of tablets on the kinetics of in vitro gliclazide release from the intact and divided tablets. Gliclazide was released from prolonged release tablets containing 30 or 60 mg of the drug into a phosphate buffer, pH 7.4 and the amount of the drug in acceptor fluid was determined by UV-Vis spectrophotometry. The dissolution profiles were fit to zero- and first-order kinetics as well as to the Korsmeyer-Peppas equation. The largest discrepancy in the values of rate constants was obtained in the case of the release of gliclazide from intact and from splitting tablets using zero- and first-order kinetics. The values of the rate constants <i>k</i><sub>0</sub> obtained from the release of the drug from the intact tablets and from fragments with a dose of the drug of 30 mg were (4.2 ± 0.1) × 10<sup>-5</sup> g min<sup>-1</sup> and (5.8 ± 0.1) × 10<sup>-5</sup> g min<sup>-1</sup>, respectively, and <i>k</i><sub>1</sub> were (2.3 ± 0.1) × 10<sup>-3</sup> min<sup>-1</sup> and (4.7 ± 0.6) × 10<sup>-3</sup> min<sup>-1</sup>, respectively. These discrepancies were confirmed by the value of <i>f</i><sub>2</sub> coefficient that was 45.9. The results suggest that physical division of tablets accelerate the release of gliclazide from its prolonged form.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 5","pages":"953-959"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2176-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36064558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Monatshefte Fur ChemiePub Date : 2018-01-01Epub Date: 2017-11-28DOI: 10.1007/s00706-017-2081-y
Miran Lemmerer, Christopher J Teskey, Daniel Kaiser, Nuno Maulide
{"title":"Regioselective synthesis of pyridines by redox alkylation of pyridine <i>N</i>-oxides with malonates.","authors":"Miran Lemmerer, Christopher J Teskey, Daniel Kaiser, Nuno Maulide","doi":"10.1007/s00706-017-2081-y","DOIUrl":"10.1007/s00706-017-2081-y","url":null,"abstract":"<p><strong>Abstract: </strong>A regioselective synthesis of pyridines by the addition of malonate anions to pyridine <i>N</i>-oxide derivatives, which have been activated by trifluoromethanesulfonic anhydride, is reported. The reaction selectively affords either 2- or 4-substituted pyridines in good yields.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"715-719"},"PeriodicalIF":1.7,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906502/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}