{"title":"Synthesis of nitroarenes and azoxyarenes through the selenium-mediated on water oxidation of aryl amines","authors":"Antonella Capperucci , Camilla Dalia , Alessio Cenni , Damiano Tanini","doi":"10.1080/10426507.2023.2166044","DOIUrl":"https://doi.org/10.1080/10426507.2023.2166044","url":null,"abstract":"<div><p>Selenium-promoted oxidations enable a broad range of valuable oxidative functional group interconversions. Anilines are oxidized with hydrogen peroxide in water in the presence of selenium catalysts. The selenium catalyst determines the nature of the oxidation product; whereas nitroarenes are obtained employing diphenyl diselenide or benzeneseleninic acid, azoxyarenes are formed using selenium dioxide or sodium seleninate. The reaction mechanism relies on the reactivity of Se(IV) active oxidants, while Se(VI) species have been demonstrated not to be involved in.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863690","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":"Optimization synthesis of phosphorous-containing natural products fosmidomycin and FR900098","authors":"Xin Wu , Hongrui Ping , Chunlin Song , Jiang Duan , Aidong Zhang","doi":"10.1080/10426507.2023.2173756","DOIUrl":"https://doi.org/10.1080/10426507.2023.2173756","url":null,"abstract":"<div><p>Fosmidomycin and its acetyl analogue FR900098 are two phosphorus-containing natural products with inhibitory activity against IspC enzyme in the 2-<em>C</em>-methyl-D-erythritol 4-phosphate (MEP) pathway of isoprenoid biosynthesis in plants and most bacteria. This work presents a facile route for the chemical synthesis of fosmidomycin and FR900098 using readily available raw materials. Through optimizing reaction conditions of the key steps of Michaelis-Becker reaction and acylation, the monosodium salts of fosmidomycin and FR900098 were obtained in yields of 60% and 66%, respectively, over six steps in the route. This unified route provides an alternative to the reported methods and makes it possible to synthesize the two valuable compounds with scalability and low cost, having the potential for application in developing new antimalarial drugs and pesticides.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49872635","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":"An overview on synthetic routes of anti-inflammatory active scaffolds including thiazole and thiazolidine cores","authors":"Ayushi Bhatnagar , Gangotri Pemawat","doi":"10.1080/10426507.2023.2189253","DOIUrl":"https://doi.org/10.1080/10426507.2023.2189253","url":null,"abstract":"<div><p>Thiazoles and thiazolidines are widespread occurring in natural products. They act as a viaduct between medicinal and organic chemistry. The presence of sulfur elevates their pharmacological activities whereas the presence of nitrogen makes it an active moiety for the development of scaffolds in a drug discovery process. Therefore, both of these compounds can be utilized as a vehicle for the synthesis of beneficial organic amalgamation. Thiazole exhibits high curative properties which enabled researchers to focus on composing various attempts to integrate and investigate novel structural precursors, which are more effective. On the other hand, thiazolidine and its derivatives are used in scrutinizing drug designs for the development of multifunctional drugs and modifying their activity. Both the nucleus and their derivative are blended in the evolution of drugs that display selective inhibition of both types of cyclooxygenases as well as lipoxygenase enzymes. In the present review, different recent synthetic routes of this important class are presented which show anti-inflammatory activities and enhanced potential in the inhibition of COX enzymes.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49700531","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}
Gaoyong Zi , Bangfu Huang , Meng Dai , Zhe Shi , Zhenjing Wen , Wanjun Li , Liubin Luo , Linjing Yang
{"title":"Effects of seed crystal concentration, pH, and stirring rate on ammonium sulfate crystallization under the action of ammonium nitrate","authors":"Gaoyong Zi , Bangfu Huang , Meng Dai , Zhe Shi , Zhenjing Wen , Wanjun Li , Liubin Luo , Linjing Yang","doi":"10.1080/10426507.2023.2175828","DOIUrl":"https://doi.org/10.1080/10426507.2023.2175828","url":null,"abstract":"<div><p>In order to explore the effect of ammonium nitrate on the crystallization of ammonium sulfate mother liquor, this paper selected crystal seed, pH and stirring rate as the influencing factors, and studied the changes of average particle size, morphology and phase structure of ammonium sulfate crystals under the action of ammonium nitrate. When the seed crystal concentration was 1%–2%, the solute growth of the mixed solution could effectively reduce the supersaturation during the evaporation process, and the crystal growth did not generate new crystal nuclei, interfering with the crystallization process. A pH value of 4–5 promotes solvent/crystal surface interaction and crystal surface growth, which is beneficial for obtaining high-quality crystals. At a stirring rate of 200–300 r/min, the nucleation rate and secondary nucleation were improved, which is conducive to solid–liquid separation.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49700533","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}
Fu-Hao Zhang , Huan Zhang , Chang-Xing Sun , Peng-Hui Li , Lin Jiang
{"title":"Synthesis and fungicidal activity of 2-(methylthio)-4-methylpyrimidine carboxamides bearing a carbamate moiety","authors":"Fu-Hao Zhang , Huan Zhang , Chang-Xing Sun , Peng-Hui Li , Lin Jiang","doi":"10.1080/10426507.2023.2192934","DOIUrl":"https://doi.org/10.1080/10426507.2023.2192934","url":null,"abstract":"<div><p>A series of 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl]ethyl-substitutedphenyl carbamates (<strong>3a</strong>–<strong>3i</strong>) were designed and synthesized, using 4-methyl-2-(methylthio)pyrimidine-5-carboxylic acid, (2-aminophenyl)ethan-1-one, and substituted phenyl isocyanates as starting materials. Their structures were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR and HRMS. The <em>in vitro</em> fungicidal activities against <em>Sclerotinia sclerotiorum</em> were evaluated, and the result showed that some compounds displayed moderate antifungal activity with >60% inhibitory rates, among which 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl] ethyl-(2- methyl phenyl)carbamate (<strong>3a</strong>) and 1-[2-(4-methyl-2-(methylthio)pyrimidine-5- carboxamido)phenyl] ethyl-(3-trifluoromethyl phenyl)carbamate (<strong>3g</strong>) held inhibitory rates of 69.5% and 70.3% at 100 mg/L, respectively. Molecular docking study showed that <strong>3g</strong> can form two hydrogen bonds and a cation-π interaction with succinate dehydrogenase.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49706815","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}
Peng Du , Lijiang Zhou , Zongwei Zhang , Xin Huang , Bo Peng
{"title":"Aromatic iodonium/sulfonium rearrangement using difluoroenol silyl ethers","authors":"Peng Du , Lijiang Zhou , Zongwei Zhang , Xin Huang , Bo Peng","doi":"10.1080/10426507.2022.2113977","DOIUrl":"https://doi.org/10.1080/10426507.2022.2113977","url":null,"abstract":"<div><p>Difluoroenol silyl ethers are a unique class of enol silyl ethers that are widely used as a powerful difluoroalkylating reagent to incorporate difluoromethylene groups into organic molecules. In this context, we revealed a fluorine effect that the difluoroenol silyl ethers exhibit the oxygen nucleophilicity in lieu of traditional α-carbon nucleophilicity toward the aromatic iodonium/sulfonium species, thus allowing us to develop difluoroalkylative [3,3]-rearrangement of aryl iodanes and aryl sulfoxides and the difluoroalkylative dearomatization of aryl sulfoxides. In this article, we summarize these works and illustrate the logic of our design.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863681","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}
Ana Rosa Lazo-Fraga , Mayra Paulina Hernández , Alicia María Díaz-García , Marcia Viltres-Portales , Osvaldo Estévez-Hernández
{"title":"3,3-Disubstituted 1-acylthioureas as ionophores for Pb(II)-ion selective electrodes: physical and chemical characterization of the sensing membranes","authors":"Ana Rosa Lazo-Fraga , Mayra Paulina Hernández , Alicia María Díaz-García , Marcia Viltres-Portales , Osvaldo Estévez-Hernández","doi":"10.1080/10426507.2022.2152814","DOIUrl":"https://doi.org/10.1080/10426507.2022.2152814","url":null,"abstract":"<div><p>Solid-state Pb(II) ion selective electrodes were developed, which are based on 3,3-disubstituted 1-acylthioureas as ionophores and use PVC membranes. 1-Benzoyl, 1-(2-furoyl), 3,3-diethyl and 3,3-diphenyl were the substituent groups on the thioureide core. The analytical parameters for the constructed electrodes were studied. The electrodes based on 3,3-diethyl substituted thiourea derivatives showed better analytical response to Pb(II) ions with suitable sensitivity and an average lifetime of more than 30 days. Cu(II), Hg(II) and Ag(I) ions were interfering species during Pb(II) detection. Scanning electron microscopy and atomic force microscopy micrographs of the activated sensing membranes revealed morphological changes, which have been associated with the performance of the sensors. The studies have suggested that the detection of few large size particles or aggregates at the membrane surface are responsible for inadequate functioning of the prepared electrodes. This pattern was mainly observed for the sensing membranes based on 3,3-diphenyl groups as substituents and is related to unfavorable steric and electronic factors. Furthermore, X-ray photoelectron spectroscopy profiles S2<em>p</em> and Pb4<em>f</em> supported chemically the analytical response displayed for the four membrane systems. The X-ray photoelectron spectroscopy results combined with scanning electron microscopy and atomic force microscopy studies shed light on the working mechanism of the studied electrodes.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49902487","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}
Emine Kutlu , Fatih Mehmet Emen , Kübra Yıldırım , Cemilenur Ataş , Ruken Esra Demirdogen , Tuncay Yesilkaynak , Neslihan Kaya Kinaytürk , Ece Şimşek , Ahmet Yılmaz Çoban
{"title":"Novel thiourea derivatives against Mycobacterium tuberculosis: synthesis, characterization and molecular docking studies","authors":"Emine Kutlu , Fatih Mehmet Emen , Kübra Yıldırım , Cemilenur Ataş , Ruken Esra Demirdogen , Tuncay Yesilkaynak , Neslihan Kaya Kinaytürk , Ece Şimşek , Ahmet Yılmaz Çoban","doi":"10.1080/10426507.2023.2201503","DOIUrl":"https://doi.org/10.1080/10426507.2023.2201503","url":null,"abstract":"<div><p> <em>N</em>-((2-chloropyridin-3-yl)carbamothioyl)thiophene-2-carboxamide (HL<sup>1</sup>), <em>N</em>-((6-methylpyridin-2-yl)carbamothioyl)thiophene-2-carboxamide (HL<sup>2</sup>), <em>N</em>-(allylcarbamothioyl)thiophene-2-carboxamide (HL<sup>3</sup>), 2-chloro-<em>N</em>-(methyl(1-phenylethyl)carbamothioyl)benzamide (HL<sup>4</sup>) and 2-chloro-<em>N</em>-(<em>bis</em>((R)-1-phenylethyl)carbamothioyl)benzamide (HL<sup>5</sup>) were synthesized and characterized via FT-IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and HR-MS techniques and HL<sup>3</sup> was characterized via a single crystal X-ray diffraction experiment. The antituberculosis activity of the synthesized thiourea derivatives was tested against the H37RV (ATCC27294), ATCC35822 (INH resistant), ATCC35838 (RIF resistant), ATCC35820 (STM resistant) and ATCC35837 (EMB resistant) standard bacteria strains. The thiourea derivatives were tested on two MDR and one primary drug-sensitive isolates with the microplate nitrate reductase test method. The results indicated that HL<sup>2</sup> and HL<sup>3</sup> had tuberculosis activity on some of the isolates. It was observed that HL<sup>4</sup> was the most effective among all the thiourea derivatives. The interaction mechanism of the synthesized compounds on 2X23, a tuberculosis protein, was investigated via molecular docking method. The interaction was observed to occur over S and Cl atoms in all the compounds. The compounds containing the methyl group were observed to interact via this group.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49709090","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}
Mohamed Hussien , Tarik E. Ali , Ibrahim El-Tantawy El Sayed , Abdelaleem Hassan Abdelaleem , H. M. Torkey
{"title":"Ultrasound-assisted construction of novel diethyl {(4-oxo-1,4-dihydroquinolin-3-yl) (aryl/heteroarylamino)methyl}phosphonates using CdI2 nanoparticles as an efficient catalyst: Synthesis, characterization, and antifungal properties","authors":"Mohamed Hussien , Tarik E. Ali , Ibrahim El-Tantawy El Sayed , Abdelaleem Hassan Abdelaleem , H. M. Torkey","doi":"10.1080/10426507.2023.2207709","DOIUrl":"https://doi.org/10.1080/10426507.2023.2207709","url":null,"abstract":"<div><p>The synthesis of some novel diethyl {(4-oxo-1,4-dihydroquinolin-3-yl)(aryl/heteroaryl-amino)methyl}phosphonates, was achieved. The methodology is based on one-pot three-component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (<strong>1</strong>), amine, and diethyl phosphite in the presence of CdI<sub>2</sub> nanoparticles as an efficient catalyst under conventional heating at 80 °C or ultrasound irradiation at 50 °C. The mild reaction conditions, operational simplicity, and excellent yields are the essential advantages of this protocol. Most of the products recorded inhibitory effects toward plant pathogenic fungi nearly to the standard control. The hybridization between diethyl α-aminophosphonate and quinolin-4-one moieties clubbed with sulfonamide, antipyrine, or 1,2,4-triazine in one molecular frame displayed good antifungal activities.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49709092","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":"A greener approach of synthesis of new 2-chloro-1,3,2-diazaphosphinin-4-one-2-oxide derivatives","authors":"Samar Kherfani , Raoudha Abderrahim","doi":"10.1080/10426507.2023.2184362","DOIUrl":"https://doi.org/10.1080/10426507.2023.2184362","url":null,"abstract":"<div><p>In this work, we describe a novel, easy and green method for the synthesis of diazaphosphinine derivatives. The new diazaphosphinines were prepared by condensation of phosphorus oxychloride with the corresponding benzamides under reflux in acetone with moderate to good yields. The structures of the new compounds were confirmed on the basis of their infrared and nuclear magnetic resonance spectral data (<sup>1</sup>H, <sup>13</sup>C, and <sup>31</sup>P), MS, and elemental analysis.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49728229","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}