Pub Date : 2024-03-03DOI: 10.1080/10426507.2024.2323018
Lu Xu , Shuangyan He , Chunlan Chi , Caiwen Li , Peipei Cui , Hongying Wang , Baoquan Chen
A series of new disulfides incorporating naphthalimide moiety were designed, synthesized and biologically evaluated against three human cancer cell lines (MCF-7, SMMC-7721 and Hela). Most of target compounds exhibited some degrees of anticancer activities, and some compounds displayed better effects than reference drugs PX-12 and 5-FU against the tested three cancer cells. Especially, compound 7d showed the most potent antiproliferative activity against MCF-7 cell lines with IC50 value of 3.19 μM. Compound 8a displayed prominent anticancer property against SMMC-7721 cell lines with IC50 value of 1.84 μM. Compound 6c possessed the most effective proliferation inhibitory activity against Hela cell lines with IC50 value of 2.14 μM. In addition, cytotoxicity evaluation indicated that most of the compounds had weak cytotoxicity to L929 cell lines.
{"title":"Synthesis and anticancer evaluation of new disulfides incorporating naphthalimide moiety","authors":"Lu Xu , Shuangyan He , Chunlan Chi , Caiwen Li , Peipei Cui , Hongying Wang , Baoquan Chen","doi":"10.1080/10426507.2024.2323018","DOIUrl":"10.1080/10426507.2024.2323018","url":null,"abstract":"<div><p>A series of new disulfides incorporating naphthalimide moiety were designed, synthesized and biologically evaluated against three human cancer cell lines (MCF-7, SMMC-7721 and Hela). Most of target compounds exhibited some degrees of anticancer activities, and some compounds displayed better effects than reference drugs PX-12 and 5-FU against the tested three cancer cells. Especially, compound <strong>7d</strong> showed the most potent antiproliferative activity against MCF-7 cell lines with IC<sub>50</sub> value of 3.19 μM. Compound <strong>8a</strong> displayed prominent anticancer property against SMMC-7721 cell lines with IC<sub>50</sub> value of 1.84 μM. Compound <strong>6c</strong> possessed the most effective proliferation inhibitory activity against Hela cell lines with IC<sub>50</sub> value of 2.14 μM. In addition, cytotoxicity evaluation indicated that most of the compounds had weak cytotoxicity to L929 cell lines.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140072075","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}
Pub Date : 2024-03-03DOI: 10.1080/10426507.2024.2320672
Efe Doğukan Dincel , Ebru Didem Kuran , Beyza Onarer , Yusuf Fıstıkçı , İlhami Gülçin , Nuray Ulusoy-Güzeldemirci
In this work, 1,2,4-triazole derived hydrazide–hydrazones were synthesized with a five-step synthesis pathway. The novel derivatives were characterized by various analytical methods. Acetylcholinesterase (AChE), and human carbonic anhydrase (hCA) inhibitory qualifications of these thirteen original compounds (4, 5a–l) were also determined. The overall biological activity results were very interesting. The reported compounds were found to be very effective inhibitors of hCA I, hCA II, and AChE enzymes with IC50 values in the range of 17.33−77.00 nM for hCA I (Acetazolamide IC50: 62.80 nM), 13.07−46.20 nM for hCA II (Acetazolamide IC50: 57.75 nM) and 4.91−36.47 nM for AChE (Tacrine IC50: 28.88 nM). Within the new compounds, 5i displayed the best hCA I, hCA II and AChE inhibitory activities with IC50 values of 17.33 nM, 13.07 nM, and 4.91 nM, respectively.
{"title":"Synthesis and in vitro carbonic anhydrase and acetylcholinesterase inhibitory activities of novel hydrazide–hydrazone compounds containing 1,2,4-triazole ring","authors":"Efe Doğukan Dincel , Ebru Didem Kuran , Beyza Onarer , Yusuf Fıstıkçı , İlhami Gülçin , Nuray Ulusoy-Güzeldemirci","doi":"10.1080/10426507.2024.2320672","DOIUrl":"10.1080/10426507.2024.2320672","url":null,"abstract":"<div><p>In this work, 1,2,4-triazole derived hydrazide–hydrazones were synthesized with a five-step synthesis pathway. The novel derivatives were characterized by various analytical methods. Acetylcholinesterase (AChE), and human carbonic anhydrase (hCA) inhibitory qualifications of these thirteen original compounds (<strong>4</strong>, <strong>5a</strong>–<strong>l</strong>) were also determined. The overall biological activity results were very interesting. The reported compounds were found to be very effective inhibitors of hCA I, hCA II, and AChE enzymes with IC<sub>50</sub> values in the range of 17.33−77.00 nM for hCA I (Acetazolamide IC<sub>50</sub>: 62.80 nM), 13.07−46.20 nM for hCA II (Acetazolamide IC<sub>50</sub>: 57.75 nM) and 4.91−36.47 nM for AChE (Tacrine IC<sub>50</sub>: 28.88 nM). Within the new compounds, <strong>5i</strong> displayed the best hCA I, hCA II and AChE inhibitory activities with IC<sub>50</sub> values of 17.33 nM, 13.07 nM, and 4.91 nM, respectively.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140032930","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}
Pub Date : 2024-03-03DOI: 10.1080/10426507.2024.2316794
Wei-Xiu Pang , Yun-Bin Sun , Jian-Jun Zhao , Mei-Shan Wang , Xiao-Min Song
The potential interstellar medium molecule, thiirane, has received considerable attention of experimental and theoretical studies in recent years. The anharmonic force field and spectroscopic constants of thiirane are calculated using CCSD(T) and B3LYP methods employing correlation consistent basis sets. Molecular structure, ground state rotational constants, quartic and sextic centrifugal distortion constants, and fundamental frequencies of thiirane are compared with the available experimental data. The B3LYP and CCSD(T) results can reproduce them well. The rotational parameters and vibrational wave numbers of isotopologues for thiirane are also determined using B3LYP method. The new data obtained in this study might be used to assist astronomical search for thiirane.
{"title":"Spectroscopic constants and anharmonic force field of thiirane: a theoretical study","authors":"Wei-Xiu Pang , Yun-Bin Sun , Jian-Jun Zhao , Mei-Shan Wang , Xiao-Min Song","doi":"10.1080/10426507.2024.2316794","DOIUrl":"10.1080/10426507.2024.2316794","url":null,"abstract":"<div><p>The potential interstellar medium molecule, thiirane, has received considerable attention of experimental and theoretical studies in recent years. The anharmonic force field and spectroscopic constants of thiirane are calculated using CCSD(T) and B3LYP methods employing correlation consistent basis sets. Molecular structure, ground state rotational constants, quartic and sextic centrifugal distortion constants, and fundamental frequencies of thiirane are compared with the available experimental data. The B3LYP and CCSD(T) results can reproduce them well. The rotational parameters and vibrational wave numbers of isotopologues for thiirane are also determined using B3LYP method. The new data obtained in this study might be used to assist astronomical search for thiirane.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139902560","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}
This work presents the design and the synthesis of precursors of hexadentate bisphosphonic ligands able to complex iron cation. This study describes coupling reaction between natural siderophore entity and bisphosphonic acids. These latter have properties of complexing heavy metals. These compounds were obtained from amidation reaction between a protected and activated bisphosphonic compound and serine trilactone. In the intermediate species, all the hydroxyl groups of phosphorus are esterified with ethyl group. The coupling method gave access to triserinelactone-bisphosphonate conjugates in good yields.
{"title":"Towards the synthesis of new sequestring hexadentate bisphosphonic ligands for iron ion chelation","authors":"Mouna Ouechtati , Christelle Kouame , Julia Deschamp , Thibaut Legigan , Soufiane Touil , Evelyne Migianu-Griffoni , Maelle Monteil , Marc Lecouvey","doi":"10.1080/10426507.2024.2316787","DOIUrl":"10.1080/10426507.2024.2316787","url":null,"abstract":"<div><p>This work presents the design and the synthesis of precursors of hexadentate bisphosphonic ligands able to complex iron cation. This study describes coupling reaction between natural siderophore entity and bisphosphonic acids. These latter have properties of complexing heavy metals. These compounds were obtained from amidation reaction between a protected and activated bisphosphonic compound and serine trilactone. In the intermediate species, all the hydroxyl groups of phosphorus are esterified with ethyl group. The coupling method gave access to triserinelactone-bisphosphonate conjugates in good yields.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140006841","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}
Pub Date : 2024-03-03DOI: 10.1080/10426507.2024.2323020
Jing Li , Xiaodong Zhou , Yue Lin , Bingling Liu , Wenyang Chen , Chengcai Liu
The development of new antibacterial agents is particularly important in the battle against pathogenic microorganisms. In this study, sulfonium ions were used as the structural core to synthesize alkyl-substituted ionic compounds as antibacterial agents. The antimicrobial activity of sulfonium ionic compounds against Escherichia coli and Staphylococcus aureus was analyzed by measurement of the minimum inhibitory concentration and minimum bactericidal concentration. The effects of sulfonium salts on cell membrane integrity and permeability were investigated by detecting the extracellular proteins leakage of E. coli and S. aureus upon contact treatment, and observing the bacteria’s ultrastructural changes with transmission electron microscopy. The results showed that all the sulfonium salts exhibited resistant activity. Sulfonium salt with alkyl chain length of 16 carbon presented the strongest resistance with MIC of 30 and 3.75 μmol/L, and MBC of 120 and 60 μmol/L against E. coli and S. aureus, respectively. After treatment with sulfonium salts, the permeability of the membrane of E. coli and S. aureus cells changed, and the exudation of extracellular proteins increased significantly. The transmission electron microscope showed that the surface of the bacteria had shrunk and the cell walls had burst. The group of sulfonium salt compounds can destroy the integrity of cell membrane and change membrane permeability to achieve antibacterial purposes.
在与病原微生物的斗争中,开发新型抗菌剂尤为重要。本研究以磺离子为结构核心,合成了一种...
{"title":"Synthesis and antibacterial properties of alkyl substituted sulfonium salt","authors":"Jing Li , Xiaodong Zhou , Yue Lin , Bingling Liu , Wenyang Chen , Chengcai Liu","doi":"10.1080/10426507.2024.2323020","DOIUrl":"10.1080/10426507.2024.2323020","url":null,"abstract":"<div><p>The development of new antibacterial agents is particularly important in the battle against pathogenic microorganisms. In this study, sulfonium ions were used as the structural core to synthesize alkyl-substituted ionic compounds as antibacterial agents. The antimicrobial activity of sulfonium ionic compounds against <em>Escherichia coli</em> and <em>Staphylococcus aureus</em> was analyzed by measurement of the minimum inhibitory concentration and minimum bactericidal concentration. The effects of sulfonium salts on cell membrane integrity and permeability were investigated by detecting the extracellular proteins leakage of <em>E. coli</em> and <em>S. aureus</em> upon contact treatment, and observing the bacteria’s ultrastructural changes with transmission electron microscopy. The results showed that all the sulfonium salts exhibited resistant activity. Sulfonium salt with alkyl chain length of 16 carbon presented the strongest resistance with MIC of 30 and 3.75 μmol/L, and MBC of 120 and 60 μmol/L against <em>E. coli</em> and <em>S. aureus</em>, respectively. After treatment with sulfonium salts, the permeability of the membrane of <em>E. coli</em> and <em>S. aureus</em> cells changed, and the exudation of extracellular proteins increased significantly. The transmission electron microscope showed that the surface of the bacteria had shrunk and the cell walls had burst. The group of sulfonium salt compounds can destroy the integrity of cell membrane and change membrane permeability to achieve antibacterial purposes.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140032867","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}
Pub Date : 2024-02-01DOI: 10.1080/10426507.2023.2281499
Zahra Ayagh , Mohammad H. Mosslemin , Mohammad R. Nateghi , Alireza Hassanabadi
We report an efficient method for the synthesis of 2-aryl-6-hydroxymethyl-1-phenyl-4-selenoxo-1,4-dihydro-pyrano[3,2-d]pyrimidin-8-one from the condensation of potassium selenocyanate and aromatic acyl chlorides with 2-hydroxymethyl-5-phenylamino-pyran-4-one in the presence of catalytic amounts of N-methylimidazole under solvent-free conditions. This new protocol offers advantages such as mild reaction conditions, short reaction time, easy work-up, high yield products, and does not involve any hazardous solvent.
{"title":"Three-component reaction between 2-hydroxymethyl-5-phenylamino-pyran-4-one and aromatic acyl chlorides with potassium selenocyanate: Synthesis of 2-aryl-6-hydroxymethyl-1-phenyl-4-selenoxo-1,4-dihydro-pyrano[3,2-d]pyrimidin-8-one","authors":"Zahra Ayagh , Mohammad H. Mosslemin , Mohammad R. Nateghi , Alireza Hassanabadi","doi":"10.1080/10426507.2023.2281499","DOIUrl":"10.1080/10426507.2023.2281499","url":null,"abstract":"<div><p>We report an efficient method for the synthesis of 2-aryl-6-hydroxymethyl-1-phenyl-4-selenoxo-1,4-dihydro-pyrano[3,2-d]pyrimidin-8-one from the condensation of potassium selenocyanate and aromatic acyl chlorides with 2-hydroxymethyl-5-phenylamino-pyran-4-one in the presence of catalytic amounts of <em>N</em>-methylimidazole under solvent-free conditions. This new protocol offers advantages such as mild reaction conditions, short reaction time, easy work-up, high yield products, and does not involve any hazardous solvent.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138513448","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}
Pub Date : 2024-02-01DOI: 10.1080/10426507.2023.2281475
Yassine Ennaciri , Mohammed Bettach , Hanan El Alaoui-Belghiti
This study presents an efficient and sustainable procedure for converting phosphogypsum (PG) waste, along with hydrofluoric acid (HF) and ammonia (NH3), into valuable materials. The results obtained demonstrate the high efficiency of this proposed procedure, resulting in the synthesis of relatively pure calcium fluoride (CaF2) nanoparticles and ammonium sulfate ((NH4)2SO4). The latter is recommended for agricultural use as a fertilizer, while the obtained CaF2 can be utilized in the metallurgical industry. Furthermore, this procedure not only offers a solution for reducing fluorine gas emissions and managing PG waste but also contributes to the conservation of fluorite reserves.
{"title":"Obtaining nano calcium fluoride and ammonium sulfate from phosphogypsum","authors":"Yassine Ennaciri , Mohammed Bettach , Hanan El Alaoui-Belghiti","doi":"10.1080/10426507.2023.2281475","DOIUrl":"10.1080/10426507.2023.2281475","url":null,"abstract":"<div><p>This study presents an efficient and sustainable procedure for converting phosphogypsum (PG) waste, along with hydrofluoric acid (HF) and ammonia (NH<sub>3</sub>), into valuable materials. The results obtained demonstrate the high efficiency of this proposed procedure, resulting in the synthesis of relatively pure calcium fluoride (CaF<sub>2</sub>) nanoparticles and ammonium sulfate ((NH<sub>4</sub>)<sub>2</sub>SO<sub>4</sub>). The latter is recommended for agricultural use as a fertilizer, while the obtained CaF<sub>2</sub> can be utilized in the metallurgical industry. Furthermore, this procedure not only offers a solution for reducing fluorine gas emissions and managing PG waste but also contributes to the conservation of fluorite reserves.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138513461","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}
Pub Date : 2024-02-01DOI: 10.1080/10426507.2023.2281489
Yassine Ennaciri , Mohammed Bettach
Phosphogypsum (PG) is an acidic by-product that is created during the production of phosphoric acid using the sulfuric acid route. The management of PG poses a significant environmental challenge worldwide due to its large quantity and chemical composition. While PG primarily consists of calcium sulfate dihydrate, it also contains various impurities such as phosphorus, fluoride, heavy metals, and radionuclides. These toxic impurities, when present in high concentrations, can have adverse effects on the environment and human health. In this review, we provide a detailed examination of the behavior of the most abundant impurities found in PG. Furthermore, we discuss the factors that influence the presence of different types of impurities in PG. Understanding the overall behavior of these impurities is crucial for selecting appropriate environmental methods for PG management and identifying suitable avenues for its valorization.
{"title":"The chemical behavior of the different impurities present in Phosphogypsum: a review","authors":"Yassine Ennaciri , Mohammed Bettach","doi":"10.1080/10426507.2023.2281489","DOIUrl":"10.1080/10426507.2023.2281489","url":null,"abstract":"<div><p>Phosphogypsum (PG) is an acidic by-product that is created during the production of phosphoric acid using the sulfuric acid route. The management of PG poses a significant environmental challenge worldwide due to its large quantity and chemical composition. While PG primarily consists of calcium sulfate dihydrate, it also contains various impurities such as phosphorus, fluoride, heavy metals, and radionuclides. These toxic impurities, when present in high concentrations, can have adverse effects on the environment and human health. In this review, we provide a detailed examination of the behavior of the most abundant impurities found in PG. Furthermore, we discuss the factors that influence the presence of different types of impurities in PG. Understanding the overall behavior of these impurities is crucial for selecting appropriate environmental methods for PG management and identifying suitable avenues for its valorization.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138513463","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}
Pub Date : 2024-02-01DOI: 10.1080/10426507.2023.2281472
Cécile Garzon , Mireille Attolini , Michel Maffei
β-Substituted vinylphosphonates constitute an original class of organophosphorus reagents of which several compounds exhibit attractive biological properties. The review exemplifies and discusses the different synthetic methods described for their synthesis, which involve well known reactions, but also more specifically designed methods. In addition, the uses as synthetic intermediates as well as the therapeutic uses of the title compounds are also summarized.
{"title":"Synthesis, synthetic interests, and biological activities of β-substituted vinylphosphonates","authors":"Cécile Garzon , Mireille Attolini , Michel Maffei","doi":"10.1080/10426507.2023.2281472","DOIUrl":"10.1080/10426507.2023.2281472","url":null,"abstract":"<div><p>β-Substituted vinylphosphonates constitute an original class of organophosphorus reagents of which several compounds exhibit attractive biological properties. The review exemplifies and discusses the different synthetic methods described for their synthesis, which involve well known reactions, but also more specifically designed methods. In addition, the uses as synthetic intermediates as well as the therapeutic uses of the title compounds are also summarized.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138513447","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}
Pub Date : 2024-02-01DOI: 10.1080/10426507.2023.2281473
Hao Wei , Cunzhi Chen , Aijun Gao , Zhanhui Yang
As a proof of concept, P-chiral monodentate phosphines, which were inactive in promoting the transannulations of 1,2,3-thiadiazoles, were proven viable in the asymmetric catalytic (3 + 2) transannulations of 1,2,3-thiadiazoles with a strained bicyclic alkene. Polycyclic dihydrothiophenes with four newly formed stereocenters are generated in moderate 19-72% yields and 11-27% enantiopurities.
{"title":"Rh(I)-catalyzed enantioselective (3 + 2) transannulations of 1,2,3-thiadiazoles with P-chiral monodentate phosphines","authors":"Hao Wei , Cunzhi Chen , Aijun Gao , Zhanhui Yang","doi":"10.1080/10426507.2023.2281473","DOIUrl":"10.1080/10426507.2023.2281473","url":null,"abstract":"<div><p>As a proof of concept, <em>P</em>-chiral monodentate phosphines, which were inactive in promoting the transannulations of 1,2,3-thiadiazoles, were proven viable in the asymmetric catalytic (3 + 2) transannulations of 1,2,3-thiadiazoles with a strained bicyclic alkene. Polycyclic dihydrothiophenes with four newly formed stereocenters are generated in moderate 19-72% yields and 11-27% enantiopurities.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.3,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138513446","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}