Monatshefte Fur ChemiePub Date : 2019-01-01Epub Date: 2019-04-29DOI: 10.1007/s00706-019-2381-5
Elias Tanuhadi, Ioannis Kampatsikas, Gerald Giester, Annette Rompel
{"title":"Synthesis, characterization, and POM-protein interactions of a Fe-substituted Krebs-type Sandwich-tungstoantimonate.","authors":"Elias Tanuhadi, Ioannis Kampatsikas, Gerald Giester, Annette Rompel","doi":"10.1007/s00706-019-2381-5","DOIUrl":"10.1007/s00706-019-2381-5","url":null,"abstract":"<p><strong>Abstract: </strong>The novel iron-substituted Krebs-type polyoxotungstate (C<sub>12</sub>N<sub>4</sub>H<sub>11</sub>)<sub>4</sub>Na<sub>2</sub>H<sub>5</sub>[(Fe(H<sub>2</sub>O)<sub>3</sub>)<sub>2</sub>((FeO<sub>2</sub>)<sub>0.5</sub>(WO<sub>2</sub>)<sub>0.5</sub>)<sub>2</sub>(β-SbW<sub>9</sub>O<sub>33</sub>)<sub>2</sub>] (<b>Fe-1</b>) has been synthesized using <i>ortho</i>-phenylenediamine (opda) as a precursor for the in situ formation of the counter cation 2,3-diaminophenazinium (C<sub>12</sub>N<sub>4</sub>H<sub>11</sub>)<sup>+</sup> (2,3-DAP). <b>Fe-1</b> has been thoroughly characterized in the solid state by single-crystal X-ray diffraction (SXRD), powder X-ray diffraction (PXRD), IR spectroscopy, and elemental analysis as well as in solution by UV-Vis spectroscopy. The crystal structure of <b>Fe-1</b> reveals <i>π-π</i>-interactions between the aromatic systems of the unconventional 2,3-DAP counter cation. POM-protein interaction studies using SDS-PAGE revealed a non-proteolytic behavior of <b>Fe-1</b> towards Human Serum Albumin (HSA) as a model protein.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 5","pages":"871-875"},"PeriodicalIF":1.7,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6533222/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37317152","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 : 2019-01-01Epub Date: 2019-04-29DOI: 10.1007/s00706-019-02390-x
Christoph Falschlunger, Ronald Micura
{"title":"Efficient access to <i>N</i>-trifluoroacetylated 2'-amino-2'-deoxyadenosine phosphoramidite for RNA solid-phase synthesis.","authors":"Christoph Falschlunger, Ronald Micura","doi":"10.1007/s00706-019-02390-x","DOIUrl":"10.1007/s00706-019-02390-x","url":null,"abstract":"<p><strong>Abstract: </strong>Here, we present a robust synthetic route to a 2'-amino-2'-deoxyadenosine phosphoramidite building block for automated RNA solid-phase synthesis. The thus accessible 2'-amino-modified RNA finds applications in the evaluation of hydrogen-bond networks in folded RNA, such as riboswitches or ribozymes. In this context, we previously implemented the here described 2'-amino-2'-deoxyadenosine building block in a comparative study on self-cleaving pistol ribozymes to shed light on structural versus catalytic roles of active-site 2'-OH groups in the reaction mechanism.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 5","pages":"795-800"},"PeriodicalIF":1.7,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6534076/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37317149","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":"Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives.","authors":"Gökçe Cihan-Üstündağ, Lieve Naesens, Dilek Şatana, Gonca Erköse-Genç, Emel Mataracı-Kara, Gültaze Çapan","doi":"10.1007/s00706-019-02457-9","DOIUrl":"https://doi.org/10.1007/s00706-019-02457-9","url":null,"abstract":"<p><strong>Abstract: </strong>A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against <i>Mycobacterium tuberculosis</i> H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC<sub>50</sub> values were in the range of 1.9-12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.</p><p><strong>Graphic abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 8","pages":"1533-1544"},"PeriodicalIF":1.8,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-019-02457-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37772622","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 : 2019-01-01Epub Date: 2018-10-29DOI: 10.1007/s00706-018-2298-4
Sara Norrehed, Christoffer Karlsson, Mark E Light, Anders Thapper, Ping Huang, Adolf Gogoll
{"title":"Formation of persistent organic diradicals from <i>N</i>,<i>N'</i>-diphenyl-3,7-diazacyclooctanes.","authors":"Sara Norrehed, Christoffer Karlsson, Mark E Light, Anders Thapper, Ping Huang, Adolf Gogoll","doi":"10.1007/s00706-018-2298-4","DOIUrl":"10.1007/s00706-018-2298-4","url":null,"abstract":"<p><strong>Abstract: </strong><i>N</i>,<i>N'</i>-Diphenyl-3,7-diazacyclooctane and structurally related <i>N</i>,<i>N'</i>-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C-C coupling reaction to produce dication-diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 1","pages":"77-84"},"PeriodicalIF":1.8,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320754/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36896070","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 : 2019-01-01Epub Date: 2019-03-01DOI: 10.1007/s00706-019-2351-y
Iwona E Głowacka, Dorota G Piotrowska, Graciela Andrei, Dominique Schols, Robert Snoeck, Andrzej E Wróblewski
{"title":"Acyclic nucleoside phosphonates containing the amide bond: hydroxy derivatives.","authors":"Iwona E Głowacka, Dorota G Piotrowska, Graciela Andrei, Dominique Schols, Robert Snoeck, Andrzej E Wróblewski","doi":"10.1007/s00706-019-2351-y","DOIUrl":"https://doi.org/10.1007/s00706-019-2351-y","url":null,"abstract":"<p><strong>Abstract: </strong>To study the influence of a linker rigidity and changes in donor-acceptor properties, three series of nucleotide analogs containing a P-X-HN-C(O)- residue (X=CH(OH)CH<sub>2</sub>, CH(OH)CH<sub>2</sub>CH<sub>2</sub>, CH<sub>2</sub>CH(OH)CH<sub>2</sub>) as a replacement for the P-CH<sub>2</sub>-O-CHR- fragment in acyclic nucleoside phosphonates, e.g., adefovir, cidofovir, were synthesized. EDC proved to provide good yields of the analogs from the respective ω-amino-1- or -2-hydroxyalkylphosphonates and nucleobase-derived acetic acids. New phosphorus-nucleobase linkers are characterized by two fragments of the restricted rotation within amide bonds and in four-atom units (P-CH(OH)-CH<sub>2</sub>-N, P-CH(OH)-CH<sub>2</sub>-C and P-CH<sub>2</sub>-CH(OH)-C) in which antiperiplanar disposition of P and N/C atoms was deduced from <sup>1</sup>H and <sup>13</sup>C NMR spectral data. The synthesized analogs P-X-HNC(O)-CH<sub>2</sub>B [X=CH(OH)CH<sub>2</sub>, CH(OH)CH<sub>2</sub>CH<sub>2</sub>, CH<sub>2</sub>CH(OH)CH<sub>2</sub>] appeared inactive in antiviral assays on a wide variety of DNA and RNA viruses at concentrations up to 100 μM, while two phosphonates showed cytostatic activity towards myeloid leukemia (K-562) and multiple myeloma cells (MM.1S) with IC<sub>50</sub> of 28.8 and 40.7 μM, respectively.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 4","pages":"733-745"},"PeriodicalIF":1.8,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-019-2351-y","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37772621","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 : 2019-01-01Epub Date: 2018-10-19DOI: 10.1007/s00706-018-2279-7
Nikolaus Gorgas, Aleksandra Ilic, Karl Kirchner
{"title":"Chemoselective transfer hydrogenation of aldehydes in aqueous media catalyzed by a well-defined iron(II) hydride complex.","authors":"Nikolaus Gorgas, Aleksandra Ilic, Karl Kirchner","doi":"10.1007/s00706-018-2279-7","DOIUrl":"10.1007/s00706-018-2279-7","url":null,"abstract":"<p><strong>Abstract: </strong>An iron(II) hydride PNP pincer complex is applied as catalyst for the chemoselective transfer hydrogenation of aldehydes using an aqueous solution of sodium formate as hydrogen source. A variety of aromatic, heteroaromatic, and aliphatic aldehydes could be reduced to the corresponding alcohols in good to excellent yields with a catalyst loading of 1.0 mol% at 80 °C and 1 h reaction time. If present, C-C double bonds remained unaffected in course of the reaction, even when they are conjugated to the carbonyl group of the aldehyde. The catalyst's lifetime and activity could be improved when the reactions were conducted in an ionic liquid-based micro emulsion.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 1","pages":"121-126"},"PeriodicalIF":1.7,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320750/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36879193","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 : 2019-01-01Epub Date: 2019-05-11DOI: 10.1007/s00706-019-02427-1
Manuel Zoidl, Andreas Wolfsgruber, Michael Schalli, Seyed A Nasseri, Patrick Weber, Arnold E Stütz, Stephen G Withers, Tanja M Wrodnigg
{"title":"Synthesis of modified 1,5-imino-d-xylitols as ligands for lysosomal <i>β</i>-glucocerebrosidase.","authors":"Manuel Zoidl, Andreas Wolfsgruber, Michael Schalli, Seyed A Nasseri, Patrick Weber, Arnold E Stütz, Stephen G Withers, Tanja M Wrodnigg","doi":"10.1007/s00706-019-02427-1","DOIUrl":"10.1007/s00706-019-02427-1","url":null,"abstract":"<p><strong>Abstract: </strong>Modified 1,5-dideoxy-1,5-imino-d-xylitol analogues with different substitution patterns involving position C-1 and/or the ring nitrogen were prepared, which were designed to serve as precursors for the preparation of iminoxylitol-based ligands and tools for the elucidation and modulation of human lysosomal <i>β</i>-glucocerebrosidase. Biological evaluation of the synthesized glycomimetics with a series of glycoside hydrolases revealed that these substitution patterns elicit excellent <i>β</i>-glucosidase selectivities.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 5","pages":"831-842"},"PeriodicalIF":1.7,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6534063/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37317151","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: 2017-12-01DOI: 10.1007/s00706-017-2058-x
Edyta Kuliszewska, Friedrich Hammerschmidt
{"title":"On the rearrangement of <i>N</i>-aryl-<i>N</i>-Boc-phosphoramidates to <i>N</i>-Boc-protected <i>o</i>-aminoarylphosphonates.","authors":"Edyta Kuliszewska, Friedrich Hammerschmidt","doi":"10.1007/s00706-017-2058-x","DOIUrl":"https://doi.org/10.1007/s00706-017-2058-x","url":null,"abstract":"<p><strong>Abstract: </strong>Various arylamines were converted in two steps to <i>N</i>-Boc-<i>N</i>-arylphosphoramidates. LiTMP and LDA induced directed <i>ortho</i>-metalation at temperatures from -78 to 0 °C. The ensuing [1,3]-migration of the phosphorus atom with its substituents from the nitrogen to the <i>ortho</i>-carbanionic carbon atom gave <i>N</i>-Boc-protected <i>o</i>-aminoarylphosphonates. The nature of the substituent of 3-substituted phenylphosphoramidates strongly influenced the regioselectivity of phosphonate formation. A crossover experiment with a deuterated phosphoramidate proved the intramolecular course of the rearrangement. Three representative <i>N</i>-Boc-<i>o</i>-aminoarylphosphonates were deprotected to access the corresponding <i>o</i>-aminoarylphosphonic acids.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 1","pages":"87-98"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2058-x","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35699349","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: 2018-01-11DOI: 10.1007/s00706-017-2074-x
Bernhard J Müller, Günter Mistlberger, Ingo Klimant
{"title":"Insights in the determination of saxitoxin with fluorogenic crown ethers in water.","authors":"Bernhard J Müller, Günter Mistlberger, Ingo Klimant","doi":"10.1007/s00706-017-2074-x","DOIUrl":"10.1007/s00706-017-2074-x","url":null,"abstract":"<p><strong>Abstract: </strong>In this contribution, we present new insights and a critical discussion in the optical detection of saxitoxin using fluorophores with crown ethers. Fluorescence enhancement is caused by the reduction of photoinduced electron transfer upon complexation with the analyte. Our attempts to improve this detection method neither did yield a functioning sensor nor were the attempts to reproduce published data in this area successful. Due to the fact that only low concentrations of saxitoxin are available, multiple surrogates were investigated at high concentrations. However, no turn on response was observed. Moreover, a fluorescent decomposition product of saxitoxin that forms under UV light was discovered which was in our opinion misinterpreted as a sensor response by previous publications.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 3","pages":"493-497"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5859042/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35944694","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}