Pub Date : 2021-05-21DOI: 10.1080/10426507.2021.1927032
Wafa Arar, A. Khatyr, M. Knorr, Lukas Brieger, A. Krupp, C. Strohmann, M. Efrit, A. Ben Akacha
Abstract The phosphonothioamidates (EtO)2P(=O)C(=S)N(H)R (L1 R = Cy; L2 R = Bz) have been prepared by nucleophilic addition of K[(EtO)2P(=O)] to R–N = C=S and crystallographically analyzed. Both compounds are associated pairwise through strong intermolecular N–H···O bonding giving rise to 10-membered supramolecular macrocycles. This intermolecular bonding has also been studied by Hirshfeld analysis of L1 and L2. Complexation of L on CuI in MeCN solution affords the dinuclear rhomboid-shaped thione complexes [{Cu(μ2-I)2Cu}(η1-L)2] (1a,b). Crystallographic characterization of 1a reveals that L1 is ligated exclusively via the thione function to the trigonal Cu(I) centers, which are interconnected through a short Cu–Cu bond of 2.6207(4) Å. In the solid state, individual dimeric complexes are associated through intermolecular N–H···O bonding generating a supramolecular 1D ribbon. The dinuclear complexes [{XHg(μ2-X)2HgX}(η1-L)2] (2a X = Br, L = Cy; 2b X = Br, L = Bz; 2c X = I, L = Bz) were formed by stoichiometric addition of L to HgX2. The molecular structures of 2b and 2c have been elucidated by X-ray diffraction studies, which show that individual complexes are connected through intermolecular N–H···O bonding generating a supramolecular 1D ribbon. Treatment of L1 with two equivalents of HgBr2 produces the tetranuclear compound [Hg4Br8(κ1-L1)2] 3, whose unusual bromide-bridged architecture has been elucidated by X-ray crystallography. GRAPHICAL ABSTRACT
摘要:硫代膦酸酯(EtO)2P(=O)C(=S)N(H)R (L1 R = Cy;通过K[(EtO)2P(=O)]与R - n = C=S的亲核加成制备了L2 R = Bz，并对其进行了晶体学分析。这两种化合物通过强大的分子间N-H···O键成对结合，形成10元超分子大环。这种分子间键也通过L1和L2的Hirshfeld分析进行了研究。L在MeCN溶液中与CuI络合得到双核菱形硫酮配合物[{Cu(μ2-I)2Cu}(η1-L)2] (1a,b)。1a的晶体学表征表明，L1完全通过硫酮函数连接到三角形Cu(I)中心，它们通过一个短的Cu - Cu键(2.6207(4)Å)相互连接。在固体状态下，单个二聚体配合物通过分子间的N-H···O键结合，形成超分子一维带。双核的复合物[{XHg(μ2 X) 2 hgx}(η1 L) 2] (2 X = Br, L = Cy;b X = Br, L = Bz;22c X = I, L = Bz)由L加入HgX2形成。通过x射线衍射研究证实了2b和2c的分子结构，表明单个配合物通过分子间N-H···O键连接，形成超分子一维带。用两种等价物HgBr2处理L1会产生四核化合物[Hg4Br8(κ1-L1)2] 3，其不寻常的溴桥结构已被x射线晶体学阐明。图形抽象
{"title":"Synthesis, crystal structures and Hirshfeld analyses of phosphonothioamidates (EtO)2P(=O)C(=S)N(H)R (R = Cy, Bz) and their coordination on CuI and HgX2 (X = Br, I)","authors":"Wafa Arar, A. Khatyr, M. Knorr, Lukas Brieger, A. Krupp, C. Strohmann, M. Efrit, A. Ben Akacha","doi":"10.1080/10426507.2021.1927032","DOIUrl":"https://doi.org/10.1080/10426507.2021.1927032","url":null,"abstract":"Abstract The phosphonothioamidates (EtO)2P(=O)C(=S)N(H)R (L1 R = Cy; L2 R = Bz) have been prepared by nucleophilic addition of K[(EtO)2P(=O)] to R–N = C=S and crystallographically analyzed. Both compounds are associated pairwise through strong intermolecular N–H···O bonding giving rise to 10-membered supramolecular macrocycles. This intermolecular bonding has also been studied by Hirshfeld analysis of L1 and L2. Complexation of L on CuI in MeCN solution affords the dinuclear rhomboid-shaped thione complexes [{Cu(μ2-I)2Cu}(η1-L)2] (1a,b). Crystallographic characterization of 1a reveals that L1 is ligated exclusively via the thione function to the trigonal Cu(I) centers, which are interconnected through a short Cu–Cu bond of 2.6207(4) Å. In the solid state, individual dimeric complexes are associated through intermolecular N–H···O bonding generating a supramolecular 1D ribbon. The dinuclear complexes [{XHg(μ2-X)2HgX}(η1-L)2] (2a X = Br, L = Cy; 2b X = Br, L = Bz; 2c X = I, L = Bz) were formed by stoichiometric addition of L to HgX2. The molecular structures of 2b and 2c have been elucidated by X-ray diffraction studies, which show that individual complexes are connected through intermolecular N–H···O bonding generating a supramolecular 1D ribbon. Treatment of L1 with two equivalents of HgBr2 produces the tetranuclear compound [Hg4Br8(κ1-L1)2] 3, whose unusual bromide-bridged architecture has been elucidated by X-ray crystallography. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86089936","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-05-18DOI: 10.1080/10426507.2021.1927031
Xinyun Liu, Hang Li, X. Yin
Abstract In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates. Graphical Abstract
{"title":"NaOH-promoted one-pot aryl isothiocyanate synthesis under mild benchtop conditions","authors":"Xinyun Liu, Hang Li, X. Yin","doi":"10.1080/10426507.2021.1927031","DOIUrl":"https://doi.org/10.1080/10426507.2021.1927031","url":null,"abstract":"Abstract In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83295455","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-05-11DOI: 10.1080/10426507.2021.2012676
M. Karabörk, Ban Abdullelah Muhammed, M. Tümer, Serhan Uruş
Abstract Organosilane-functionalized and chemically activated graphene-supported Schiff base ligand were synthesized and characterized with XRD, SEM, EDX, TEM, UV–vis, FT-IR, and TG/DTA techniques. Graphene oxide (GO) obtained with the route of Hummer’s method was reacted with 3-(trimethoxysilyl)propylamine, then, the organosilane functionalized and amine-activated-GO was reacted with 3,5-di-tert-butylsalicylaldehyde obtained the hybrid material containing azomethine group on GO surface. The material was used as an adsorbent in order to remove cobalt(II) and zinc(II) ions in drinking water and standard solutions. The adsorption capacity of the material to cobalt(II) and zinc(II) ions were investigated by using batch method. The effect of pH, contact time, temperature, and concentration on the adsorption capacity of the material was also investigated. The enrichment factors were calculated as 441 and 675 for zinc(II) and cobalt(II), respectively. The recovery performance of the material was determined in 98.65–101.75% and 98.55–104.0% range for zinc(II) and cobalt(II) ions, respectively. Graphical Abstract
{"title":"Organosilane-functionalized graphene oxide hybrid material: Efficient adsorbent for heavy metal ions in drinking water","authors":"M. Karabörk, Ban Abdullelah Muhammed, M. Tümer, Serhan Uruş","doi":"10.1080/10426507.2021.2012676","DOIUrl":"https://doi.org/10.1080/10426507.2021.2012676","url":null,"abstract":"Abstract Organosilane-functionalized and chemically activated graphene-supported Schiff base ligand were synthesized and characterized with XRD, SEM, EDX, TEM, UV–vis, FT-IR, and TG/DTA techniques. Graphene oxide (GO) obtained with the route of Hummer’s method was reacted with 3-(trimethoxysilyl)propylamine, then, the organosilane functionalized and amine-activated-GO was reacted with 3,5-di-tert-butylsalicylaldehyde obtained the hybrid material containing azomethine group on GO surface. The material was used as an adsorbent in order to remove cobalt(II) and zinc(II) ions in drinking water and standard solutions. The adsorption capacity of the material to cobalt(II) and zinc(II) ions were investigated by using batch method. The effect of pH, contact time, temperature, and concentration on the adsorption capacity of the material was also investigated. The enrichment factors were calculated as 441 and 675 for zinc(II) and cobalt(II), respectively. The recovery performance of the material was determined in 98.65–101.75% and 98.55–104.0% range for zinc(II) and cobalt(II) ions, respectively. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-05-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78876236","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Abstract In this work, we have developed a simple one-step synthesis of Ni2P and CoP phosphides based on a carbonization process. The current approach uses glucose as a reductant instead of H2 and employs inert gas as feed gas. The Ni2P/C and CoP/C obtained by the glucose route showed higher CH4-CO2 reforming performance than corresponding phosphides prepared by traditional H2 reduction method, which should be attributed to the fact that the phosphides prepared by glucose route had higher surface areas and smaller particle sizes than the ones prepared by traditional method. GRAPHICAL ABSTRACT
{"title":"A simple glucose route to nickel and cobalt phosphide catalysts","authors":"Wanting Zhang, Wei-Wei Ding, Zhiwei Yao, Yanlung. Shi, Yuejian Sun, Xiaoxue Kang","doi":"10.1080/10426507.2021.1924171","DOIUrl":"https://doi.org/10.1080/10426507.2021.1924171","url":null,"abstract":"Abstract In this work, we have developed a simple one-step synthesis of Ni2P and CoP phosphides based on a carbonization process. The current approach uses glucose as a reductant instead of H2 and employs inert gas as feed gas. The Ni2P/C and CoP/C obtained by the glucose route showed higher CH4-CO2 reforming performance than corresponding phosphides prepared by traditional H2 reduction method, which should be attributed to the fact that the phosphides prepared by glucose route had higher surface areas and smaller particle sizes than the ones prepared by traditional method. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84310049","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-11-28DOI: 10.1080/10426507.2020.1854254
Fouzia Bouchareb, M. Berredjem, A. Bouzina, Meriem Guerfi
Abstract We report a rapid, efficient, economic, environmentally benign, and easy to scale-up method for the synthesis of phosphonamide derivatives using ultrasound irradiation, under catalyst and solvent-free conditions starting from the corresponding amine and phenyl phosphonic dichloride. The reaction was achieved in excellent isolated yield in a short reaction time at room temperature. The structures of the synthesized compounds are confirmed by elemental analysis as well as by IR and 1H, 13C, 31P NMR spectroscopic data and mass spectrometry. Graphical Abstract
{"title":"Ultrasound-promoted, rapid and green synthesis of phosphonamide derivatives under catalyst and solvent-free conditions","authors":"Fouzia Bouchareb, M. Berredjem, A. Bouzina, Meriem Guerfi","doi":"10.1080/10426507.2020.1854254","DOIUrl":"https://doi.org/10.1080/10426507.2020.1854254","url":null,"abstract":"Abstract We report a rapid, efficient, economic, environmentally benign, and easy to scale-up method for the synthesis of phosphonamide derivatives using ultrasound irradiation, under catalyst and solvent-free conditions starting from the corresponding amine and phenyl phosphonic dichloride. The reaction was achieved in excellent isolated yield in a short reaction time at room temperature. The structures of the synthesized compounds are confirmed by elemental analysis as well as by IR and 1H, 13C, 31P NMR spectroscopic data and mass spectrometry. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90092916","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-11-28DOI: 10.1080/10426507.2020.1854255
I. Nizamov, T. Belov, I. Nizamov, Yevgeniy N. Nikitin, Gulnaz R. Akhmedova, Olga Shilnikova, I. D. Timushev, R. Salikhov, M. Shulaeva, O. K. Pozdeev, E. S. Batyeva, R. Cherkasov
Abstract Pyridoxonium salts of chiral linear and cyclic dithiophosphoric acids were obtained by the reactions of pyridoxine with bis{2-О-[2-methyl-(2S)-3-O-propionyl]}, bis{2-О-[1,4-О,О-dimethyl-(2S)-succinyl]}, and O,O-di-2-butyl dithiophosphoric acids, and cyclic dithiophosphoric acids of 1,3,2-dioxaphosphorinane, 1,3,2-dioxaphospholane, and 1,3,2-dioxaphosphepin structure. Syntheses of acetonide pyridoxonium О,О-dimenthyl dithiophosphates were carried out by the reaction of seven-membered pyridoxine acetonide with О,О-dimenthyl dithiophosphoric acids obtained from (–)-(1 R,2S,5R)-menthol and (+)-(1S,2R,5S)-menthol. Diacetonide pyridoxonium bisdithiophosphonate was also prepared. The antibacterial and antifungal activities of pyridoxonium chiral linear and cyclic dithiophosphates were evaluated. Graphical Abstract
{"title":"Pyridoxonium salts of chiral and cyclic dithiophosphoric and bisdithiophosphonic acids and their antimicrobial activities","authors":"I. Nizamov, T. Belov, I. Nizamov, Yevgeniy N. Nikitin, Gulnaz R. Akhmedova, Olga Shilnikova, I. D. Timushev, R. Salikhov, M. Shulaeva, O. K. Pozdeev, E. S. Batyeva, R. Cherkasov","doi":"10.1080/10426507.2020.1854255","DOIUrl":"https://doi.org/10.1080/10426507.2020.1854255","url":null,"abstract":"Abstract Pyridoxonium salts of chiral linear and cyclic dithiophosphoric acids were obtained by the reactions of pyridoxine with bis{2-О-[2-methyl-(2S)-3-O-propionyl]}, bis{2-О-[1,4-О,О-dimethyl-(2S)-succinyl]}, and O,O-di-2-butyl dithiophosphoric acids, and cyclic dithiophosphoric acids of 1,3,2-dioxaphosphorinane, 1,3,2-dioxaphospholane, and 1,3,2-dioxaphosphepin structure. Syntheses of acetonide pyridoxonium О,О-dimenthyl dithiophosphates were carried out by the reaction of seven-membered pyridoxine acetonide with О,О-dimenthyl dithiophosphoric acids obtained from (–)-(1 R,2S,5R)-menthol and (+)-(1S,2R,5S)-menthol. Diacetonide pyridoxonium bisdithiophosphonate was also prepared. The antibacterial and antifungal activities of pyridoxonium chiral linear and cyclic dithiophosphates were evaluated. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86855031","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-11-25DOI: 10.1080/10426507.2020.1845678
S. Türk, F. Tok, Ö. Erdoğan, Ö. Çevik, T. Tok, B. Koçyiğit-Kaymakçıoğlu, S. Karakuş
Abstract 2-(1-((3-Substitutedureido/thioureido)methyl)cyclohexyl)acetic acid derivatives (1–9) were synthesized from gabapentin. All the synthesized compounds were characterized by using IR, 1H-NMR, 13C-NMR spectroscopy, mass spectrometry and elemental analysis. Urea and thiourea derivatives were investigated for their potential in vitro anticancer activities on PC3 and MCF7 cancer cell lines using MTT assay. Cell apoptosis was detected by with Annexin V Assay. Our results showed that compound 8 {2-(1-((3-(2,6-dichlorophenyl)ureido)methyl)cyclohexyl)acetic acid} significantly inhibited the proliferation and growing of PC3 and MCF7 cells. Both cell types showed dysfunction of cellular morphology which induced apoptosis 10 µM concentration of compound 8 treated cells. Our results indicate that compound 8 might have significance as an anti-tumor agent against human prostate and breast cancer. The theoretical structure and activity estimation via in silico ADMET was also examined. Graphical Abstract
{"title":"Synthesis, anticancer evaluation and in silico ADMET studies on urea/thiourea derivatives from gabapentin","authors":"S. Türk, F. Tok, Ö. Erdoğan, Ö. Çevik, T. Tok, B. Koçyiğit-Kaymakçıoğlu, S. Karakuş","doi":"10.1080/10426507.2020.1845678","DOIUrl":"https://doi.org/10.1080/10426507.2020.1845678","url":null,"abstract":"Abstract 2-(1-((3-Substitutedureido/thioureido)methyl)cyclohexyl)acetic acid derivatives (1–9) were synthesized from gabapentin. All the synthesized compounds were characterized by using IR, 1H-NMR, 13C-NMR spectroscopy, mass spectrometry and elemental analysis. Urea and thiourea derivatives were investigated for their potential in vitro anticancer activities on PC3 and MCF7 cancer cell lines using MTT assay. Cell apoptosis was detected by with Annexin V Assay. Our results showed that compound 8 {2-(1-((3-(2,6-dichlorophenyl)ureido)methyl)cyclohexyl)acetic acid} significantly inhibited the proliferation and growing of PC3 and MCF7 cells. Both cell types showed dysfunction of cellular morphology which induced apoptosis 10 µM concentration of compound 8 treated cells. Our results indicate that compound 8 might have significance as an anti-tumor agent against human prostate and breast cancer. The theoretical structure and activity estimation via in silico ADMET was also examined. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83377761","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-11-24DOI: 10.1080/10426507.2020.1854258
G. Sravya, A. Balakrishna, G. Zyryanov, G. Mohan, C. S. Reddy, N. Bakthavatchala Reddy
Abstract The review discusses recent achievements in the development of more ecofriendly and economically viable processes for the synthesis of biologically potent α-aminophosphonates via Kabachnik-Fields reaction by three-component coupling of carbonyl, amine and hydrophosphoryl compounds. These α-aminophosphonates exhibited promising antioxidant, antimicrobial and anticancer activity. Some recent developments on the synthesis of biologically active α-aminophosphonates in the presence of various catalysts, in catalytic solvent medium, in catalyst-free solvent medium, under solvent-free conditions, and reactions in solution are discussed. Miscellaneous reactions are also included. Graphical Abstract
{"title":"Synthesis of α-aminophosphonates by the Kabachnik-Fields reaction","authors":"G. Sravya, A. Balakrishna, G. Zyryanov, G. Mohan, C. S. Reddy, N. Bakthavatchala Reddy","doi":"10.1080/10426507.2020.1854258","DOIUrl":"https://doi.org/10.1080/10426507.2020.1854258","url":null,"abstract":"Abstract The review discusses recent achievements in the development of more ecofriendly and economically viable processes for the synthesis of biologically potent α-aminophosphonates via Kabachnik-Fields reaction by three-component coupling of carbonyl, amine and hydrophosphoryl compounds. These α-aminophosphonates exhibited promising antioxidant, antimicrobial and anticancer activity. Some recent developments on the synthesis of biologically active α-aminophosphonates in the presence of various catalysts, in catalytic solvent medium, in catalyst-free solvent medium, under solvent-free conditions, and reactions in solution are discussed. Miscellaneous reactions are also included. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75394635","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-11-12DOI: 10.1080/10426507.2020.1845680
Roqayeh Khadem Moghaddam, Ghasem Aghapour
Abstract A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry. Graphical Abstract
{"title":"One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system","authors":"Roqayeh Khadem Moghaddam, Ghasem Aghapour","doi":"10.1080/10426507.2020.1845680","DOIUrl":"https://doi.org/10.1080/10426507.2020.1845680","url":null,"abstract":"Abstract A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72677590","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2020-11-10DOI: 10.1080/10426507.2020.1845679
Sk. Md. Altaff, T. Raja Rajeswari, Ch. Subramanyam
Abstract We have synthesized a series of phosphoramidates containing a heterocyclic moiety with good yields (88–95%) by the reaction of (E)-5-benzylidene-3-((2-hydroxyethoxy)methyl)thiazolidine-2,4-dione with ethyl phosphorodichloridate followed by the reaction with various heterocyclic amines. The designed compounds were primarily screened for their ability to inhibit pancreatic α-amylase enzyme using in silico molecular docking approach. The compounds with good binding energies (−8.0 to −6.9 kcal/mol) when compared with standard drug, acarbose (−8.0 kcal/mol) were prompted for the synthesis. The structures of the newly prepared compounds were confirmed by their spectroscopic analyses. They were further screened in vitro for their inhibition toward α-amylase enzyme using acarbose as standard drug. All compounds exhibited moderate to good inhibition potential with IC50 values in the range of 54.14 ± 0.35 to 185.04 ± 0.53 µg/mL when compared with the standard drug (IC50, 50.47 ± 0.28 µg/mL). Especially, the compound (E)-2-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methoxy)ethyl ethyl 1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylphosphoramidate (6f) (IC50, 54.14 ± 0.35 µg/mL) and (E)-2-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methoxy)ethyl ethyl benzo[d]thiazol-2-ylphosphoramidate (6c) (IC50, 57.02 ± 0.32 µg/mL) exhibited the best inhibition among the synthesized compounds. Graphical abstract
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