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Practical synthesis of N-(di-n-butylamino)methylene-protected 2-aminopurine riboside phosphoramidite for RNA solid-phase synthesis. 用于RNA固相合成的N-（二正丁基氨基）亚甲基保护的2-氨基嘌呤核糖侧磷酰胺的实际合成。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2019-10-11 DOI: 10.1007/s00706-019-02502-7
Eva Neuner, Ronald Micura
{"title":"Practical synthesis of <i>N</i>-(di-<i>n</i>-butylamino)methylene-protected 2-aminopurine riboside phosphoramidite for RNA solid-phase synthesis.","authors":"Eva Neuner,&nbsp;Ronald Micura","doi":"10.1007/s00706-019-02502-7","DOIUrl":"10.1007/s00706-019-02502-7","url":null,"abstract":"","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 11","pages":"1941-1946"},"PeriodicalIF":1.8,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-019-02502-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37536708","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}
引用次数: 1
Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives. 新型螺环吲哚衍生物的设计、合成、抗结核和抗病毒性能。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2019-07-17 DOI: 10.1007/s00706-019-02457-9
Gökçe Cihan-Üstündağ, Lieve Naesens, Dilek Şatana, Gonca Erköse-Genç, Emel Mataracı-Kara, Gültaze Çapan
{"title":"Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives.","authors":"Gökçe Cihan-Üstündağ,&nbsp;Lieve Naesens,&nbsp;Dilek Şatana,&nbsp;Gonca Erköse-Genç,&nbsp;Emel Mataracı-Kara,&nbsp;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}
引用次数: 17
Formation of persistent organic diradicals from N,N'-diphenyl-3,7-diazacyclooctanes. 由 N,N'-二苯基-3,7-二氮杂环辛烷形成持久性有机二卤化物。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2018-10-29 DOI: 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}
引用次数: 0
On the formation of seven-membered rings by arene-ynamide cyclization. 通过炔酰胺环化形成七元环。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2018-11-16 DOI: 10.1007/s00706-018-2320-x
Bogdan R Brutiu, Wilhelm Andrei Bubeneck, Olivera Cvetkovic, Jing Li, Nuno Maulide
{"title":"On the formation of seven-membered rings by arene-ynamide cyclization.","authors":"Bogdan R Brutiu, Wilhelm Andrei Bubeneck, Olivera Cvetkovic, Jing Li, Nuno Maulide","doi":"10.1007/s00706-018-2320-x","DOIUrl":"10.1007/s00706-018-2320-x","url":null,"abstract":"<p><strong>Abstract: </strong>A Brønsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 1","pages":"3-10"},"PeriodicalIF":1.8,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320749/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36924057","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}
引用次数: 0
Rhodium-catalyzed direct alkylation of benzylic amines using alkyl bromides. 铑催化烷基溴直接烷基化苄胺。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2018-11-13 DOI: 10.1007/s00706-018-2305-9
Martin Anschuber, Robert Pollice, Michael Schnürch
{"title":"Rhodium-catalyzed direct alkylation of benzylic amines using alkyl bromides.","authors":"Martin Anschuber,&nbsp;Robert Pollice,&nbsp;Michael Schnürch","doi":"10.1007/s00706-018-2305-9","DOIUrl":"https://doi.org/10.1007/s00706-018-2305-9","url":null,"abstract":"<p><p></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 1","pages":"127-138"},"PeriodicalIF":1.8,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-018-2305-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36879194","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}
引用次数: 1
Acyclic nucleoside phosphonates containing the amide bond: hydroxy derivatives. 含酰胺键的无环核苷膦酸盐;羟基衍生物。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2019-03-01 DOI: 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,&nbsp;Dorota G Piotrowska,&nbsp;Graciela Andrei,&nbsp;Dominique Schols,&nbsp;Robert Snoeck,&nbsp;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}
引用次数: 1
Chemoselective transfer hydrogenation of aldehydes in aqueous media catalyzed by a well-defined iron(II) hydride complex. 一种定义明确的氢化物铁（II）配合物催化水介质中醛的化学选择性转移加氢反应。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2018-10-19 DOI: 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":1.8,"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}
引用次数: 0
Synthesis of modified 1,5-imino-d-xylitols as ligands for lysosomal β-glucocerebrosidase. 作为溶酶体 β-葡糖脑配体的改性 1,5-亚氨基-d-xylitols 的合成。
IF 1.7 4区 化学
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2019-05-11 DOI: 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}
引用次数: 0
On the rearrangement of N-aryl-N-Boc-phosphoramidates to N-Boc-protected o-aminoarylphosphonates. n -芳基- n - boc -磷酸酯重排为n - boc保护的邻氨基芳基膦酸盐。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2017-12-01 DOI: 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,&nbsp;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}
引用次数: 3
A computational model to predict the Diels-Alder reactivity of aryl/alkyl-substituted tetrazines. 芳基/烷基取代四嗪Diels-Alder反应性的计算模型。
IF 1.8 4区 化学
Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2017-11-29 DOI: 10.1007/s00706-017-2110-x
Dennis Svatunek, Christoph Denk, Hannes Mikula
{"title":"A computational model to predict the Diels-Alder reactivity of aryl/alkyl-substituted tetrazines.","authors":"Dennis Svatunek,&nbsp;Christoph Denk,&nbsp;Hannes Mikula","doi":"10.1007/s00706-017-2110-x","DOIUrl":"https://doi.org/10.1007/s00706-017-2110-x","url":null,"abstract":"<p><strong>Abstract: </strong>The tetrazine ligation is one of the fastest bioorthogonal ligations and plays a pivotal role in time-critical in vitro and in vivo applications. However, prediction of the reactivity of tetrazines in inverse electron demand Diels-Alder-initiated ligation reactions is not straight-forward. Commonly used tools such as frontier molecular orbital theory only give qualitative and often even wrong results. Applying density functional theory, we have been able to develop a simple computational method for the prediction of the reactivity of aryl/alkyl-substituted tetrazines in inverse electron demand Diels-Alder reactions.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"149 4","pages":"833-837"},"PeriodicalIF":1.8,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-017-2110-x","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36031585","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}
引用次数: 13
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