{"title":"Spectral study of phosphonium salts synthesized from Michael acceptors","authors":"Elleuch Haitham , Ferid Yaccoubi","doi":"10.1080/10426507.2022.2150854","DOIUrl":"https://doi.org/10.1080/10426507.2022.2150854","url":null,"abstract":"<div><p>The synthesis of new phosphonium salts derived from Michael acceptors <em>via</em> a one-pot reaction process and the study of their NMR characteristics is described. The simple and rapid 1,4 addition of triphenylphosphine to the Michael acceptors in the presence of HBr (48%) (5 equivalents) was carried out at room temperature to give the corresponding phosphonium salts with excellent yields.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 4","pages":"Pages 354-365"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49728234","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Stable cysteine sulfenic acid: synthesis by direct oxidation of a thiol, crystallographic analysis, and elucidation of reactivities","authors":"Kei Goto , Tsukasa Sano , Ryosuke Masuda , Shotaro Otaka , Ryutaro Kimura , Shohei Sase , Satoru Kuwano","doi":"10.1080/10426507.2023.2195650","DOIUrl":"https://doi.org/10.1080/10426507.2023.2195650","url":null,"abstract":"<div><p>A small-molecule cysteine sulfenic acid (Cys–SOH) was synthesized and isolated as stable crystals, for the first time, by utilizing a nanosized molecular cavity as a protective cradle. The cradled Cys–SOH was synthesized by direct oxidation of the corresponding cysteine thiol with H<sub>2</sub>O<sub>2</sub> under basic conditions and its structure was established by X-ray crystallographic analysis. In the reaction of the cradled Cys–SOH with a thiol to produce the disulfide, a remarkable acceleration was observed upon the addition of an amine base. This suggests the important role of base in the reaction of Cys–SOH with thiols in biological systems. The cradled Cys–SOH was reduced to the cysteine thiol by dithiothreitol or triphenylphosphine. The high stability and sufficient reactivity of the cradled Cys–SOH indicate its usefulness as a small-molecule model compound for better understanding the chemical behavior of Cys–SOH in biological systems.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 466-470"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863684","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Catalyst-free thia-Diels-Alder click reaction for the labeling of peptides for imaging applications","authors":"Timothé Maujean , Patrice Marchand , Patrick Wagner , Stéphanie Riché , Frédéric Boisson , Nicolas Girard , Julie Karpenko , Dominique Bonnet , Mihaela Gulea","doi":"10.1080/10426507.2023.2165659","DOIUrl":"https://doi.org/10.1080/10426507.2023.2165659","url":null,"abstract":"<div><p>A thia-Diels-Alder reaction between a phosphonodithioester and a highly reactive exocyclic diene for the chemoselective labeling of peptides under catalyst-free mild conditions is described. An efficient method to introduce the dithioester function into a model tripeptide was first developed and then applied to two bioactive peptides, PSMA and apelin-13. The tripeptide-dithioester was used to optimize the cycloaddition with dienes bearing fluorine-18 or a fluorophore. Then, the cycloaddition of the PSMA-dithioester with the <sup>18</sup>F-diene led to a new PSMA-radiotracer, which was used for in vivo Positron Emission Tomography (PET) imaging. In the same way, a fluorescent apelin-13 probe was obtained from the apelin-dithioester and a squaraine-linked diene before beingused for in cellulo optical imaging.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 532-535"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863691","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Subarna Roy , Subhadeep Sen , Samiran Saha , Sandip Kumar Deb , Bhagat Singh , Goutam Biswas
{"title":"Design, synthesis and molecular docking studies of 5-fluoro 1-aryl/alkyl sulfonyl benzimidazole derivatives for treatment of Parkinson’s disease","authors":"Subarna Roy , Subhadeep Sen , Samiran Saha , Sandip Kumar Deb , Bhagat Singh , Goutam Biswas","doi":"10.1080/10426507.2022.2150852","DOIUrl":"https://doi.org/10.1080/10426507.2022.2150852","url":null,"abstract":"<div><p>Novel sulfonyl derivatives of 5-fluoro-substituted benzimidazole were synthesized and characterized by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, <sup>19</sup>F-NMR and mass spectrometry. Molecular docking study against monoamine oxidase B (MAO-B), responsible for Parkinson’s disease (PD), was performed. The binding energy and interactions with active amino acid residues in the binding site of newly synthesized derivatives, as well as conventional inhibitors (Selegiline and Rasagiline), were investigated and presented. According to the docking scores predicted by ADV (AutoDock vina) and AD (AutoDock), most of the synthesized derivatives have higher binding affinity toward MAO-B than the conventional inhibitors. This study shows that these fluoro-substituted benzimidazole derivatives can be developed into essential drugs for the treatment of PD. The antibacterial property of these compounds was investigated by disk diffusion test and minimum inhibitory concentration (MIC), against gram-negative and gram-positive bacteria. And the results were further verified by the bacteria kill test with respect to time. All the synthesized compounds demonstrated considerable antibacterial activity against both bacterial strains. Therefore, this work focuses on defining the efficiency of different types of sulfonyl derivatives of fluorinated benzimidazole in biomedical research for the treatment of PD highlighting their versatile biological properties.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 4","pages":"Pages 336-344"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49700418","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Microwave assisted, Cu-catalyzed synthesis of sulfonamides using sodium sulfinates and amines","authors":"Anil Nikam , Jagannath Jadhav , Sagar Sankpal","doi":"10.1080/10426507.2023.2198714","DOIUrl":"https://doi.org/10.1080/10426507.2023.2198714","url":null,"abstract":"<div><p>An efficient procedure has been developed under microwave irradiation for the monosulfonylation of amines in acetonitrile:water. In this reaction, equimolar quantities of amines and sodium sulfinates were reacted in presence of CuBr<sub>2</sub> and omitted the use of oxidants, ligands, additives, and bases. The developed methodology converts a wide array of sterically and electronically diverse sulfinate and amines into the corresponding sulfonamides in excellent yields within a short reaction time. The use of microwave and aqueous media makes this protocol potentially useful in the development of a green strategy for the synthesis of sulfonamides.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 10","pages":"Pages 800-807"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49704500","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
H. Bendjeffal , H. Mamine , T. Metidji , A. Djebli , R. Diaf , Y. Bouhedja
{"title":"A Box-Behnken design-based chemometric approach to optimize the removal of phosphate ions from water using Punica granatum shells","authors":"H. Bendjeffal , H. Mamine , T. Metidji , A. Djebli , R. Diaf , Y. Bouhedja","doi":"10.1080/10426507.2023.2174542","DOIUrl":"https://doi.org/10.1080/10426507.2023.2174542","url":null,"abstract":"<div><p>The present study was aimed at evaluating the adsorption of phosphate ions using <em>Punica granatum</em> shells (PGS) as an environmentally friendly and economical sorbent material. The PGS powder was characterized by several techniques including BET, <span><math><msub><mrow><mi>p</mi><mi>H</mi></mrow><mrow><mi>pzc</mi></mrow></msub><mo>,</mo></math></span> SEM, and FTIR, as well as its adsorption capacity evaluated with the sorption of <span><math><msubsup><mrow><mi>P</mi><mi>O</mi></mrow><mrow><mn>4</mn></mrow><mrow><mn>3</mn><mo>−</mo></mrow></msubsup></math></span> from water. To achieve adequate removal of <span><math><msubsup><mrow><mi>P</mi><mi>O</mi></mrow><mrow><mn>4</mn></mrow><mrow><mn>3</mn><mo>−</mo></mrow></msubsup></math></span> from water, a chemometric method based on the Box–Behnken design was applied to optimize the influence of the main operating factors such as the PGS amount (0.10–1 g L<sup>−1</sup>), medium pH (3–9), and <span><math><msubsup><mrow><mi>P</mi><mi>O</mi></mrow><mrow><mn>4</mn></mrow><mrow><mn>3</mn><mo>−</mo></mrow></msubsup></math></span> initial concentration (10–100 mg L<sup>−1</sup>) on the adsorption processes. Noteworthy, the best adsorption amount (29.31 mg g<sup>−1</sup>) was obtained at a pollutant dose of 72.72 mg L<sup>−1</sup>, an adsorbent quantity of 1 g L<sup>−1</sup> in medium acid pH 3 at 25 °C. The modeling study suggests that the process of <span><math><msubsup><mrow><mi>P</mi><mi>O</mi></mrow><mrow><mn>4</mn></mrow><mrow><mn>3</mn><mo>−</mo></mrow></msubsup></math></span> uptake follows the pseudo-second-order model with a maximum adsorbent quantity of 32.25 mg g<sup>−1</sup>.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 8","pages":"Pages 632-644"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49706627","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chenghao Tang , Xingju Chen , Shengzhou Yang , Wenbo Guo , Xiumei Yang , Pei Li , Xiang Wang
{"title":"Discovery of novel carbazole derivatives containing a 1,3,4-thiadiazole moiety as antifungal candidates","authors":"Chenghao Tang , Xingju Chen , Shengzhou Yang , Wenbo Guo , Xiumei Yang , Pei Li , Xiang Wang","doi":"10.1080/10426507.2023.2191961","DOIUrl":"https://doi.org/10.1080/10426507.2023.2191961","url":null,"abstract":"<div><p>Fifteen novel carbazole derivatives of 2-(9<em>H</em>-carbazol-9-yl)-<em>N</em>-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide were designed, synthesized and evaluated for their antifungal activities against <em>Pellicularia sasakii</em> (<em>P. sasakii</em>), <em>Fusarium oxysporum</em> (<em>F. oxysporum</em>), <em>Gibberella zeae</em> (<em>G. zeae</em>), <em>Phytophthora infestans</em> (<em>P. infestans</em>), <em>Cytospora mandshurica</em> (<em>C. mandshurica</em>) and <em>Capsicum wilt</em> (<em>C. wilt</em>). The results of antifungal activity tests indicated that the inhibitory rates of compounds 2-(2-chloro-9<em>H</em>-carbazol-9-yl)-<em>N</em>-(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)acetamide (<strong>3h</strong>) and 2-(2-chloro-9<em>H</em>-carbazol-9-yl)-<em>N</em>-(5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)acetamide (<strong>3o</strong>) against <em>P. sasakii</em> were 72.89% and 74.29%, respectively, which displayed better bioactivity compared with commercial fungicides hymexazol (53.09%) and carbendazim (69.65%). Meanwhile, compounds 2-(9<em>H</em>-carbazol-9-yl)-<em>N</em>-(5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)acetamide (<strong>3f</strong>) and 2-(3-iodo-9<em>H</em>-carbazol-9-yl)-<em>N</em>-(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)acetamide (<strong>3 l</strong>) exhibited the inhibition rates of 72.40% and 67.65% against <em>C. wilt</em>, respectively, which were better than the commercial fungicides hymexazol (50.21%) and carbendazim (65.33%).</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 8","pages":"Pages 627-631"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49712579","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Targeted application of GO to improve mechanical and thermal properties of PVCS/RS composites","authors":"Milad Sheydaei , Vahid Pouraman , Milad Edraki , Ebrahim Alinia-Ahandani , Seyedeh Mozhdeh Asadi-Sadeh","doi":"10.1080/10426507.2022.2150853","DOIUrl":"https://doi.org/10.1080/10426507.2022.2150853","url":null,"abstract":"<div><p>In this study, wood–plastic composites (WPCs) were prepared from polyvinyl chloride (PVC) modified by sodium trisulfide (Na<sub>2</sub>S<sub>3</sub>) and rice straw (RS) treated with 7% sodium hydroxide solution. The results showed that after modification, 35.4 wt. % of sulfur is present in the structure of PVC containing sulfur (PVCS). The structural, morphological, thermal, and mechanical properties of the samples were investigated. As the RS fibers content in the composites increased, the thermal stability also increased but the mechanical properties decreased slightly. Moreover, the presence of sulfur in the matrix created antifungal properties that the results showed us that the PVCS can inhibit and kill <em>Aspergillus niger</em> and <em>Aspergillus brasiliensis</em>. Also, graphene oxide (GO) was added to the matrix to improve its properties. The addition of GO to composite improved the mechanical and thermal properties to extent that its mechanical properties were better than the sample without RS.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 4","pages":"Pages 345-353"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49728230","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Aneta Wróblewska , Kamil Bugaj , Jakub Łagiewka , Tomasz Girek , Jozsef Rabai , Józef Drabowicz
{"title":"Attempts to oxidize sulfides under mechanochemical conditions: synthetic and stereochemical aspects","authors":"Aneta Wróblewska , Kamil Bugaj , Jakub Łagiewka , Tomasz Girek , Jozsef Rabai , Józef Drabowicz","doi":"10.1080/10426507.2023.2193405","DOIUrl":"https://doi.org/10.1080/10426507.2023.2193405","url":null,"abstract":"<div><p>Preliminary experiments devoted to the reaction of model sulfides with several oxidation reagents under mechanochemical conditions are presented. No reaction with sodium metaperiodate and (−)-(8,8-dichlorocamphorylsulfonyl)oxaziridine was observed. An interesting selectivity was observed in the oxidation reaction of aryl trifluoromethyl sulfides with hydrogen peroxide in the presence of tungstic phosphoric acid as a catalyst. Asymmetric induction has been observed during the oxidation of methyl phenyl sulfide to the corresponding sulfoxide carried out in the presence of d-camphorsulfonic acid or beta-cyclodextrin.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 513-516"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863688","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Zixuan Zhang , Qiaoli Yan , Runli Gao , Hongmei Wang
{"title":"Advances in the study of P(O)-N bond construction","authors":"Zixuan Zhang , Qiaoli Yan , Runli Gao , Hongmei Wang","doi":"10.1080/10426507.2023.2221366","DOIUrl":"https://doi.org/10.1080/10426507.2023.2221366","url":null,"abstract":"<div><p>Phosphoramides represent an important class of organophosphorus compounds that have widespread applications in industry, agriculture, chemical synthesis as well as biomedicine. Researchers have conducted intensive and extensive studies on the properties and synthetic methods of phosphamides, including optimization and improvement of the preparative procedures and expansion of compound types. This paper presents an overview of the classical and recently reported methods for efficient construction of P-N bonds.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 10","pages":"Pages 789-799"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49729619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}