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Butadienyl Ketene: An Unexplored Intermediate in Organic Synthesis 丁二烯酮:有机合成中一种尚未开发的中间体
IF 2.5
SynOpen Pub Date : 2024-04-22 DOI: 10.1055/a-2302-3294
Maninderjeet K. Mann, Simranpreet K. Wahan, Nitin Tandon, Gaurav Bhargava
{"title":"Butadienyl Ketene: An Unexplored Intermediate in Organic Synthesis","authors":"Maninderjeet K. Mann, Simranpreet K. Wahan, Nitin Tandon, Gaurav Bhargava","doi":"10.1055/a-2302-3294","DOIUrl":"https://doi.org/10.1055/a-2302-3294","url":null,"abstract":"<p>Butadienyl ketene is a useful intermediate because of its role as a 2p-component in cycloaddition reactions with a variety of substrates such as simple or conjugated imines and dienes. This review article summarizes recent reports on the generation of butadienyl ketene in situ and their cycloaddition reactions to afford heterocyclic systems. The chemistry of butadienyl ketene is explored with a focus on its [2+2] and [4+2] cycloaddition reactions with a variety of imines and azadiene derivatives such as 1,3-diazabuta-1,3-dienes, for the synthesis of four- and six-membered heterocycles, respectively.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140637301","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
Discovery of Novel N-Acylhydrazone Derivatives as Potent Inhibitors of Sirtuin-1 发现新型 N-酰腙衍生物作为 Sirtuin-1 的强效抑制剂
IF 2.5
SynOpen Pub Date : 2024-04-04 DOI: 10.1055/s-0043-1763747
Victoria V. Lipson, Fedyr G. Yaremenko, Volodymyr M. Vakula, Svitlana V. Kovalenko, Alexander V. Kyrychenko, Sergiy M. Desenko, Petro О. Borysko, Sergiy O. Zozulya
{"title":"Discovery of Novel N-Acylhydrazone Derivatives as Potent Inhibitors of Sirtuin-1","authors":"Victoria V. Lipson, Fedyr G. Yaremenko, Volodymyr M. Vakula, Svitlana V. Kovalenko, Alexander V. Kyrychenko, Sergiy M. Desenko, Petro О. Borysko, Sergiy O. Zozulya","doi":"10.1055/s-0043-1763747","DOIUrl":"https://doi.org/10.1055/s-0043-1763747","url":null,"abstract":"<p>SIRT1 enzyme is a key family member of Silent Information Regulators (Sirtuins), which catalyze the deacetylation of proteins. Therefore, developing new SIRT1 inhibitors has potential application in treating cancer disease and age-related metabolic disorders. In this study, we synthesized a series of <i>N</i>-acylhydrazone (NAH) derivatives and performed high-throughput screening of their inhibitory activity against the recombinant SIRT1 protein by a luminescent assay. Using <i>in silico</i> screening, we identified a new NAH derivative that features both selectivity and a high binding affinity towards the active pocket of SIRT1 that are comparable to known inhibitors such as Ex527 and Sirtinol. Such high binding affinity makes the new derivatives promising alternatives to the available inhibitors and holds promise for developing better-targeted drugs against SIRT1 activity.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140576326","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
Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles 含氮杂环的四苯基甲烷衍生物
IF 2.5
SynOpen Pub Date : 2024-03-26 DOI: 10.1055/a-2274-5102
Sambasivarao Kotha, Deepshikha Singh
{"title":"Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles","authors":"Sambasivarao Kotha, Deepshikha Singh","doi":"10.1055/a-2274-5102","DOIUrl":"https://doi.org/10.1055/a-2274-5102","url":null,"abstract":"<p>We disclose a useful approach to novel tetrahedral building blocks containing <i>N</i>-heterocycles. Pyrrole was introduced on to the tetraphenylmethane (TPM) core by employing the RCM strategy, Clauson–Kaas reaction, Paal–Knorr condensation, and Ullmann coupling as key steps. In addition, various heterocyclic derivatives of TPM were prepared using nickel catalysts. We also studied the photophysical properties of the synthesized TPM derivatives containing different peripheral substituents and found that they exhibit high quantum yields.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140315242","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
Electrochemical Generation of Ketyl Radicals and Their Applications 电化学生成酮基自由基及其应用
IF 2.5
SynOpen Pub Date : 2024-03-18 DOI: 10.1055/a-2280-0055
Zhoumei Tan, Kun Xu, Chengchu Zeng
{"title":"Electrochemical Generation of Ketyl Radicals and Their Applications","authors":"Zhoumei Tan, Kun Xu, Chengchu Zeng","doi":"10.1055/a-2280-0055","DOIUrl":"https://doi.org/10.1055/a-2280-0055","url":null,"abstract":"<p>Ketyl radicals display new reactivities beyond the intrinsic electrophilicity of carbonyls. Recent progress in organic electrosynthesis has fueled the generation and utilization of ketyl radicals under ‘greener’ conditions. This graphical review summarizes these electrochemical advancements into three major categories: cross-pinacol couplings, coupling of carbonyls with alkyl radical precursors, and coupling of carbonyls with unsaturated systems (alkenes, alkynes, cyanoarenes, and N-heterocycles).</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140168794","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
Regioselective C3-Formylation of 2H-Indazoles Using Selectfluor under Microwave-Assisted Conditions 微波辅助条件下使用 Selectfluor 对 2H-Indazoles 进行区域选择性 C3-甲酰化反应
IF 2.5
SynOpen Pub Date : 2024-03-04 DOI: 10.1055/a-2266-3213
Manivel Pitchai, Mahammed Kaspady, Gopikumar Indasi, Rajesh Krishnan, Gururaju Sannakki Maheswarappa, Muthalagu Vetrichelvan, Arvind Mathur, Anuradha Gupta
{"title":"Regioselective C3-Formylation of 2H-Indazoles Using Selectfluor under Microwave-Assisted Conditions","authors":"Manivel Pitchai, Mahammed Kaspady, Gopikumar Indasi, Rajesh Krishnan, Gururaju Sannakki Maheswarappa, Muthalagu Vetrichelvan, Arvind Mathur, Anuradha Gupta","doi":"10.1055/a-2266-3213","DOIUrl":"https://doi.org/10.1055/a-2266-3213","url":null,"abstract":"<p>An efficient microwave-assisted Selectfluor-mediated regioselective C3-formylation of 2<i>H</i>-indazoles bearing a variety of alkyl and aryl substituents using DMSO as the formylating agent has been developed. This methodology provides access to 3-formyl 2<i>H</i>-indazoles with moderate to excellent yields. These functionalized indazoles are potentially useful as templates for drug discovery. Control experimental results suggest that this formylation probably proceeds through a radical pathway.</p>","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140034633","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
Synthesis of 3,4-Disubstituted Pyrroline Nitroxides Containing Diphenylphosphane or Diphenylphosphane Oxide Substituents 含二苯基膦或二苯基膦氧化物取代基的 3,4-二取代吡咯啉氮氧化物的合成
IF 2.5
SynOpen Pub Date : 2024-03-01 DOI: 10.1055/a-2264-8302
Áron Balázsi, Balázs Bognár, József Jekő, Tamás Kálai
{"title":"Synthesis of 3,4-Disubstituted Pyrroline Nitroxides Containing Diphenylphosphane or Diphenylphosphane Oxide Substituents","authors":"Áron Balázsi, Balázs Bognár, József Jekő, Tamás Kálai","doi":"10.1055/a-2264-8302","DOIUrl":"https://doi.org/10.1055/a-2264-8302","url":null,"abstract":"<p>(Methyl 4-(diphenylphosphoryl)-2,2,5,5-tetramethyl-2,5-dihydro-1<i>H</i>-pyrrole-3-carboxylate-1-yl)oxydanyl was obtained as a key intermediate of the reaction starting from 3,4-dibromo-2,2,5,5-tetramethyl-2,5-dihydro-1<i>H</i>-pyrrol-1-yloxydanyl or (methyl 2,2,5,5-tetramethyl-2,5-dihydro-1<i>H</i>-pyrrole-3-carboxylate-1-yl)oxidanyl. This key compound could be converted into an azido-specific Staudinger ligation-inducing spin label, amino- and thiol-specific spin label, or MITO-CP-like antiproliferative agent.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140017348","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
Cobalt–Magnesium and Cobalt–Calcium Heterotrimetallic Dinitrogen Complexes 钴镁和钴钙异三金属二氮化合物
IF 2.5
SynOpen Pub Date : 2024-02-07 DOI: 10.1055/a-2263-8235
Jocelyn Polanco, Theresa Knoell, A. Bakhoda
{"title":"Cobalt–Magnesium and Cobalt–Calcium Heterotrimetallic Dinitrogen Complexes","authors":"Jocelyn Polanco, Theresa Knoell, A. Bakhoda","doi":"10.1055/a-2263-8235","DOIUrl":"https://doi.org/10.1055/a-2263-8235","url":null,"abstract":"We report the use of alkaline earth metals magnesium and calcium for the reduction of the cobalt(II) complex [iPr2NN]Co(μ–Cl)2Li(thf)2 (iPr2NN = 2,4-bis-(2,6-diisopropylphenylimido)pentyl) (1) resulting in heterotrimetallic dinitrogen complexes 2 and 3 with a rare example of [Co–N2–M–N2–Co] core where M = Mg (complex 2) and Ca (complex 3). The dinitrogen ligands in complexes 2 and 3 showed weakened N–N bonds, as judged by infrared spectroscopy and the structures of 2 and 3 were confirmed by X-ray crystallography. These cobalt complexes can be isolated as pure solids that are stable in solution of non-coordinating solvents such as n-pentane or cyclohexane, as well as THF. These results demonstrate the correlation between the binding mode of the Lewis acid and N–N weakening in heterotrimetallic dinitrogen complexes.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139855578","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
Cobalt–Magnesium and Cobalt–Calcium Heterotrimetallic Dinitrogen Complexes 钴镁和钴钙异三金属二氮化合物
IF 2.5
SynOpen Pub Date : 2024-02-07 DOI: 10.1055/a-2263-8235
Jocelyn Polanco, Theresa Knoell, A. Bakhoda
{"title":"Cobalt–Magnesium and Cobalt–Calcium Heterotrimetallic Dinitrogen Complexes","authors":"Jocelyn Polanco, Theresa Knoell, A. Bakhoda","doi":"10.1055/a-2263-8235","DOIUrl":"https://doi.org/10.1055/a-2263-8235","url":null,"abstract":"We report the use of alkaline earth metals magnesium and calcium for the reduction of the cobalt(II) complex [iPr2NN]Co(μ–Cl)2Li(thf)2 (iPr2NN = 2,4-bis-(2,6-diisopropylphenylimido)pentyl) (1) resulting in heterotrimetallic dinitrogen complexes 2 and 3 with a rare example of [Co–N2–M–N2–Co] core where M = Mg (complex 2) and Ca (complex 3). The dinitrogen ligands in complexes 2 and 3 showed weakened N–N bonds, as judged by infrared spectroscopy and the structures of 2 and 3 were confirmed by X-ray crystallography. These cobalt complexes can be isolated as pure solids that are stable in solution of non-coordinating solvents such as n-pentane or cyclohexane, as well as THF. These results demonstrate the correlation between the binding mode of the Lewis acid and N–N weakening in heterotrimetallic dinitrogen complexes.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139795739","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
Synthesis of C-Glucoside Analogues of Naturally Occurring Phenyl­ethanoid O-Glucosides 天然苯乙醇 O-葡萄糖苷的 C-葡萄糖苷类似物的合成
IF 2.5
SynOpen Pub Date : 2024-01-25 DOI: 10.1055/s-0042-1751553
Amudala Subramanyam, Sumit Sumit, Indrapal S. Aidhen
{"title":"Synthesis of C-Glucoside Analogues of Naturally Occurring Phenyl­ethanoid O-Glucosides","authors":"Amudala Subramanyam, Sumit Sumit, Indrapal S. Aidhen","doi":"10.1055/s-0042-1751553","DOIUrl":"https://doi.org/10.1055/s-0042-1751553","url":null,"abstract":"<p>Structural modifications of natural products has been a highly effective approach in the search for new leads with improved biological activity, aqueous solubility, and stability. Phenylethanoid glycosides (PEGs), as natural compounds, have attracted great attention due to their promising biological activities. These activities include neuroprotection, antioxidant, immunoregulation, anti-inflammatory, and analgesic effects, as well as antitumor, antiviral, and hepatoprotective abilities. Three potent PEGs, acteoside, echinacoside, and salidroside, are gaining renewed interest in this class of compounds. However, being <i>O</i>-glycosides, PEGs have low bioavailability due to factors such as poor intestinal permeability and low hydrolytic stability. The promising pharmacological properties and the limitations have inspired us to synthesize <i>C</i>-analogues that are expected to be hydrolytically stable.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139587118","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
An Overview of Synthetic Approaches Towards 1,2,3-Triazoles 1,2,3-三唑合成方法概述
IF 2.5
SynOpen Pub Date : 2024-01-15 DOI: 10.1055/a-2245-5172
Yajat Rohila, Sharol Sebastian, Meenakshi Goyat, Manoj K Gupta
{"title":"An Overview of Synthetic Approaches Towards 1,2,3-Triazoles","authors":"Yajat Rohila, Sharol Sebastian, Meenakshi Goyat, Manoj K Gupta","doi":"10.1055/a-2245-5172","DOIUrl":"https://doi.org/10.1055/a-2245-5172","url":null,"abstract":"In this spotlight article, authors highlighted the synthetic methods of 1,2,3-triazoles from 2002 to the present","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139622506","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
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