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Chemistry of Phosphorus Ylides: Part 45 Synthesis of Phosphoranylidene Thietane, Azetidine and Thiazinane Derivatives as Potent Chemo Preventative Agents 磷酰亚胺的化学:第45部分:作为有效化学预防剂的磷酰亚胺、硫烷、氮啶和硫烷衍生物的合成
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2018-01-02 DOI: 10.6084/M9.FIGSHARE.5341228.V1
A. Hashem, M. El‐Hussieny, M. Abd‐El‐Maksoud, S. Maigali, Shaimaa T. Mansour, F. Soliman
{"title":"Chemistry of Phosphorus Ylides: Part 45 Synthesis of Phosphoranylidene Thietane, Azetidine and Thiazinane Derivatives as Potent Chemo Preventative Agents","authors":"A. Hashem, M. El‐Hussieny, M. Abd‐El‐Maksoud, S. Maigali, Shaimaa T. Mansour, F. Soliman","doi":"10.6084/M9.FIGSHARE.5341228.V1","DOIUrl":"https://doi.org/10.6084/M9.FIGSHARE.5341228.V1","url":null,"abstract":"Reactions of nucleophilic active phosphacumulenes with iso(thio)cyanate compounds were performed. The reaction products depend on the nature of the reagent, substrate and the condition of the reaction used. New heterocyclic 4-membered or 6-membered sulfur and nitrogen compounds such as phosphoranylidene thietane, azetidine and thiazinane were obtained. On the other hand, the stable phosphonium ylides with the iso(thio)cyanate afforded phosphoranylidene thiocarbamoyl derivatives. Possible reaction mechanisms are considered and the structural assignments are based on compatible analytical and spectroscopic data.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"42 1","pages":"1-9"},"PeriodicalIF":0.0,"publicationDate":"2018-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91111974","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}
引用次数: 7
Award Announcement: Laureate of the International Arbuzovs Prize in Organophosphorus Chemistry for 2017 获奖公告:2017年国际阿布佐夫有机磷化学奖得主
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-12-02 DOI: 10.1080/10426507.2017.1401846
M. Yoshifuji, I. Beletskaya, Yufen Zhao
{"title":"Award Announcement: Laureate of the International Arbuzovs Prize in Organophosphorus Chemistry for 2017","authors":"M. Yoshifuji, I. Beletskaya, Yufen Zhao","doi":"10.1080/10426507.2017.1401846","DOIUrl":"https://doi.org/10.1080/10426507.2017.1401846","url":null,"abstract":"Recently, I received a correspondence from Professor Oleg Sinyashin, Academician of the Russian Academy of Sciences at the A.E. Arbuzov Institute of Organic and Physical Chemistry in Tatarstan, Russia, and Vice Chairman of the Awarding Committee for the International Arbuzovs Prize in Organophosphorus Chemistry. He wrote: “The International Arbuzovs Prize in the Field of Organophosphorus Chemistry was established in memory of the outstandingRussian chemists, Alexander andBoris Arbuzovs, by the President of the Republic of Tatarstan in 1997. The Arbuzovs Prize is awarded biennially to an honored Russianor foreign chemist for a “single scientific achievement or a set of scientific results in the development of phosphorus chemistry” Past winners of the award include:","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"28 1","pages":"1233 - 1233"},"PeriodicalIF":0.0,"publicationDate":"2017-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78594456","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}
引用次数: 0
Editorial Board EOV 编辑委员会EOV
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-12-02 DOI: 10.1080/10426507.2017.1404309
{"title":"Editorial Board EOV","authors":"","doi":"10.1080/10426507.2017.1404309","DOIUrl":"https://doi.org/10.1080/10426507.2017.1404309","url":null,"abstract":"","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"16 1","pages":"ebi - ebi"},"PeriodicalIF":0.0,"publicationDate":"2017-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89870218","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}
引用次数: 0
Thermal and flame retardant properties of epoxy resin cured by a novel phosphorus-containing 4,4′-bisphenol novolac curing agent 新型含磷4,4′-双酚新型酚醛固化剂固化环氧树脂的热阻燃性能
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-10-16 DOI: 10.1080/10426507.2017.1358170
Jianwei Yang, Zhengzhou Wang
{"title":"Thermal and flame retardant properties of epoxy resin cured by a novel phosphorus-containing 4,4′-bisphenol novolac curing agent","authors":"Jianwei Yang, Zhengzhou Wang","doi":"10.1080/10426507.2017.1358170","DOIUrl":"https://doi.org/10.1080/10426507.2017.1358170","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A novel flame retardant curing agent for epoxy resin (EP), i.e., a DOPO (9,10-dihydro-9-oxa-10-phosphaphenan-threne-10-oxide)-containing 4,4'-bisphenol novolac (BIP-DOPO) was synthesized and characterized by Fourier transform infrared (FTIR), 1H NMR, 31P NMR spectroscopy, and gel permeation chromatography. The epoxy resin cured by BIP-DOPO itself or its mixture with a commonly used bisphenol A-formaldehyde novolac resin (NPEH720) was prepared. The flame retardancy of the cured EP thermosets were studied by limiting oxygen index (LOI), UL 94 and cone calorimeter test (CCT), and the thermal properties by thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC). The results show that the cured epoxy resin EPNP/BI/3/1, which contains 2.2% phosphorus, possesses a value of 26.2% and achieves the UL 94 V-0 rating. The data from cone calorimeter test demonstrated that the peak release rate, average heat release rate, total heat release decline sharply for the flame retarded epoxy resins, compared with those of pure ones. DSC results show that the glass-transition temperatures of cured epoxy resins decrease with increasing phosphorus content. TGA indicates that the incorporation of BIP-DOPO promotes the decomposition of epoxy resin matrix ahead of time and leads to higher char yield. The surface morphological structures of the char residues reveal that the introduction of BIP-DOPO benefits to the formation of a continuous and solid char layer on the epoxy resin material surface during combustion.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"5 1","pages":"1294 - 1300"},"PeriodicalIF":0.0,"publicationDate":"2017-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86655549","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}
引用次数: 6
Design, synthesis, and anti-TMV bioactivities of nucleobase phosphonate analogs 膦酸核碱基类似物的设计、合成及抗tmv生物活性
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-10-11 DOI: 10.1080/10426507.2017.1321649
Zhenxing Li, He-Shu Fang, Wubin Shao, Peiyi Wang, Zhi-bing Wu, Song Yang
{"title":"Design, synthesis, and anti-TMV bioactivities of nucleobase phosphonate analogs","authors":"Zhenxing Li, He-Shu Fang, Wubin Shao, Peiyi Wang, Zhi-bing Wu, Song Yang","doi":"10.1080/10426507.2017.1321649","DOIUrl":"https://doi.org/10.1080/10426507.2017.1321649","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A series of novel nucleobase derivatives and their analogues possessing diethoxyphosphoryl scaffolds were synthesized through four-step reactions and screened for their antiviral activity toward tobacco mosaic virus (TMV). Preliminary bioassays suggested that some of these simple structures displayed appreciable anti-TMV activity in vivo. Among them, compound (diethoxyphosphoryl)methyl 4-[2-(1H-benzo[d][1,2,3]triazol-1-yl)acetamido]-benzoate (a-3) exerted the strongest chemotherapeutic and protective effects against TMV with the rates of 52.8 and 72.2% at the dosage of 500 µg/mL, respectively, which were comparable with those of the commercial agricultural antiviral agent ningnanmycin (54.2 and 70.2%). Molecular docking with TMV helicases revealed that compound a-3 had strong interactions with receptor amino acid residues. Given the facile synthetic route and significant chemotherapeutic and protective potentials, compound a-3 could be further studied and exploited as a promising antiviral candidate.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"154 1","pages":"1279 - 1285"},"PeriodicalIF":0.0,"publicationDate":"2017-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84985334","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}
引用次数: 5
H-phosphonate mediated sulfonylation of 2-substituted quinoline N-oxides: One-pot strategy for the synthesis of 3/4-sulfonylquinoline derivatives h -膦酸盐介导的2-取代喹啉n -氧化物的磺化反应:一锅法合成3/4-磺酰喹啉衍生物
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-07-05 DOI: 10.1080/10426507.2017.1315422
Huili Ma, Shuyun Liu, Shaohua Zhu, Wenzhu Bi, Xiaolan Chen, Yufen Zhao
{"title":"H-phosphonate mediated sulfonylation of 2-substituted quinoline N-oxides: One-pot strategy for the synthesis of 3/4-sulfonylquinoline derivatives","authors":"Huili Ma, Shuyun Liu, Shaohua Zhu, Wenzhu Bi, Xiaolan Chen, Yufen Zhao","doi":"10.1080/10426507.2017.1315422","DOIUrl":"https://doi.org/10.1080/10426507.2017.1315422","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A series of biologically important 3/4-sulfonylquinoline derivatives was synthesized starting from easily available sodium benzenesulfinates, diethyl H-phosphonate and 2-substituted quinoline N-oxides in one-pot under metal-free conditions. H-phosphonate plays a decisive role in activating the C3-H, C4-H bonds of the 2-substituted quinoline N-oxides. The isolated 3/4-sulfonylquinolines were characterized by 1H, 13C NMR spectroscopy and HR MS.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"55 1","pages":"887 - 895"},"PeriodicalIF":0.0,"publicationDate":"2017-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90981353","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}
引用次数: 3
Oligomeric derivatives of dihydric phenols and phosphorus-containing acids: Recent studies 二氢酚和含磷酸的低聚衍生物:最新研究
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-06-30 DOI: 10.1080/10426507.2017.1295964
K. N. Kornilov
{"title":"Oligomeric derivatives of dihydric phenols and phosphorus-containing acids: Recent studies","authors":"K. N. Kornilov","doi":"10.1080/10426507.2017.1295964","DOIUrl":"https://doi.org/10.1080/10426507.2017.1295964","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT In this review, all data on synthesis, structure and chemical properties of oligomeric derivatives of dihydric phenols and phosphorus-containing acids are generalized for the first time. Methods for the synthesis of these compounds are summarized. Features of the structure, chemical properties, complexation ability, and ways of application for phosphorus and aromatic residue-containing oligomeric compounds were analyzed.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"50 1","pages":"896 - 904"},"PeriodicalIF":0.0,"publicationDate":"2017-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74832529","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}
引用次数: 2
Synthesis and antibacterial activity of novel phosphorylated flavonoid derivatives 新型磷酸化类黄酮衍生物的合成及抑菌活性研究
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-06-30 DOI: 10.1080/10426507.2017.1295963
Min Huang, Xianghui Ruan, Qin Li, Juping Zhang, Xinmin Zhong, Xiaobin Wang, Yan Xie, W. Xiao, Wei Xue
{"title":"Synthesis and antibacterial activity of novel phosphorylated flavonoid derivatives","authors":"Min Huang, Xianghui Ruan, Qin Li, Juping Zhang, Xinmin Zhong, Xiaobin Wang, Yan Xie, W. Xiao, Wei Xue","doi":"10.1080/10426507.2017.1295963","DOIUrl":"https://doi.org/10.1080/10426507.2017.1295963","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Fifteen novel phosphonate derivatives containing a flavonoid unit were designed and synthesized, based on the connection method of active fragments. The target compounds were characterized by 1H NMR, 13C NMR, 13P NMR, ESI-MS, IR, and elemental analysis. Bioassay results indicated that some of the compounds possessed an excellent inhibition activity (≥57.38%) against Xanthomonas oryzae pv.oryzae (Xoo) at a concentration of 100 µg/mL, with 50% effective concentration (EC50) values ranging from 40.29 to 66.87 µg/mL, which are superior to the commercial antibacterial agent bismerthiazol (88.51 µg/mL). Compound (2-(3-Bromophenyl)-4-oxo-4H-chromen-3-yl) diethyl phosphonate (2f) and compound (2-(4-(tert-butyl) phenyl)-4-oxo-4H-chromen-3-yl) diethyl phosphonate (2h) display better inhibition rates against Xoo even at a concentration of 50 µg/mL. Moreover, a few compounds exhibited moderate inhibitory activities against Xanhomonas axonopodis pv.citri (Xac).","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"99 1","pages":"954 - 959"},"PeriodicalIF":0.0,"publicationDate":"2017-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79250607","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}
引用次数: 2
Synthesis of stable 1,4-diionic organophosphorus compounds from the reaction between triphenylphosphine and diaroylacetylenes in the presence of 5-aryl-4-quinoxalin-2-yl-furan-2,3-diones 在5-芳基-4-喹啉-2-基呋喃-2,3-二酮存在下，三苯基膦与二芳基乙炔反应合成稳定的1,4-二离子有机磷化合物
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-06-16 DOI: 10.1080/10426507.2017.1295962
N. Y. Lisovenko, A. V. Dryahlov, M. V. Dmitriev
{"title":"Synthesis of stable 1,4-diionic organophosphorus compounds from the reaction between triphenylphosphine and diaroylacetylenes in the presence of 5-aryl-4-quinoxalin-2-yl-furan-2,3-diones","authors":"N. Y. Lisovenko, A. V. Dryahlov, M. V. Dmitriev","doi":"10.1080/10426507.2017.1295962","DOIUrl":"https://doi.org/10.1080/10426507.2017.1295962","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Novel 1,4-diionic organophosphorus compounds have been obtained efficiently from the one-pot three-component reaction of triphenylphosphine, diaroylacetylenes and 5-aryl-4-quinoxalin-2-yl-furan-2,3-diones in 1,2-dichloroethane. The synthesized compounds were characterized by different spectroscopic methods and their structure was confirmed in one case by single crystal X-ray diffraction.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"56 1","pages":"950 - 953"},"PeriodicalIF":0.0,"publicationDate":"2017-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79352303","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}
引用次数: 2
Synthesis of 4-acetyl-2(3H)-benzothiazolone: Sulfur bioisostere of benzoxazolone allelochemicals 4-乙酰基-2(3H)-苯并噻唑酮的合成:苯并恶唑酮化感物的硫生物异构体
Phosphorus Sulfur and Silicon and The Related Elements Pub Date : 2017-04-20 DOI: 10.1080/10426507.2017.1321645
M. Gerova, Filip E. Svetoslavov, B. Shivachev, R. Nikolova, O. Petrov
{"title":"Synthesis of 4-acetyl-2(3H)-benzothiazolone: Sulfur bioisostere of benzoxazolone allelochemicals","authors":"M. Gerova, Filip E. Svetoslavov, B. Shivachev, R. Nikolova, O. Petrov","doi":"10.1080/10426507.2017.1321645","DOIUrl":"https://doi.org/10.1080/10426507.2017.1321645","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A multi-step methodology for the synthesis of 4-acetyl-2(3H)-benzothiazolone was developed in order to prepare a new biomimetic analogue of benzoxazolone allelochemicals. The compound was prepared from commercially available o-toluidine in 23% overall yield. The structure of 4-acethyl-2(3H)-benzothiazolone was confirmed by NMR spectroscopy and X-ray crystallography.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"77 1","pages":"905 - 910"},"PeriodicalIF":0.0,"publicationDate":"2017-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76178683","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}
引用次数: 1
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