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Sustainable Organocatalyzed Enantioselective Catalytic Michael Additions in Betaine-Derived Deep Eutectic Solvents 甜菜碱衍生的深度共晶溶剂中可持续的有机催化对映选择性催化Michael加成
IF 2.5
SynOpen Pub Date : 2023-03-23 DOI: 10.1055/a-2117-9971
Daniela Fonseca, Ana C. Amorim, Elisabete P. Carreiro, J. Ramalho, G. Hermann, H. Federsel, A. Duarte, A. Burke
{"title":"Sustainable Organocatalyzed Enantioselective Catalytic Michael Additions in Betaine-Derived Deep Eutectic Solvents","authors":"Daniela Fonseca, Ana C. Amorim, Elisabete P. Carreiro, J. Ramalho, G. Hermann, H. Federsel, A. Duarte, A. Burke","doi":"10.1055/a-2117-9971","DOIUrl":"https://doi.org/10.1055/a-2117-9971","url":null,"abstract":"The catalyst cinchonidine-squaramide was immobilized within three different deep eutectic solvents (DES): (Betaine: D-Sorbitol: Water), (Betaine: D-Xylitol: Water) and (Betaine: D-Mannitol: Water) and evaluated in a well-known asymmetric Michael addition. These reactions provided excellent yields (up to 99%) and enantioselectivities (up to 98%) using only 1 mol% of catalyst. It was also possible to achieve 9 cycles in reactions with DES (Betaine: D-Sorbitol: Water), proving the high recyclability of this system. In the reactions realized with only 0.5 mol% of catalyst, it was possible to achieve 5 cycles and the products were obtained with high yields (up to 95%) and excellent enantioselectivities (up to 94%), using DES (Betaine: D-Sorbitol: Water).","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"374 - 380"},"PeriodicalIF":2.5,"publicationDate":"2023-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45313985","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
Click-Chemistry-Assisted Alteration of Glycosaminoglycans for Biological Applications 生物应用中糖胺聚糖的点击化学辅助修饰
IF 2.5
SynOpen Pub Date : 2023-03-03 DOI: 10.1055/s-0040-1720072
Smritilekha Bera, D. Mondal
{"title":"Click-Chemistry-Assisted Alteration of Glycosaminoglycans for Biological Applications","authors":"Smritilekha Bera, D. Mondal","doi":"10.1055/s-0040-1720072","DOIUrl":"https://doi.org/10.1055/s-0040-1720072","url":null,"abstract":"This short review describes the assistance of click chemistry in the chemical modification of glycosaminoglycans. Through an alkyne-azide 1,3-dipolar cycloaddition reaction, the chemically and physiologically stable triazole unit connects glycosaminoglycans with other labelled or attached functionalities. The synthesized glycosaminoglycan (GAG) conjugates act as drug carriers, forming hydrogels or nanohydrogels for localized drug delivery or injectable GAGs and so on. These are used in research on antithrombotic agents, protein binding, and hepatocyte growth factors, as well as in mechanistic studies of glycosaminoglycans biosynthesis and wound healing.1 Introduction2 Synthetic Modification of GAGS3 Click Chemistry4 Modification of GAGS Applying Click Chemistry5 Conclusions6 Abbreviations","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"277 - 289"},"PeriodicalIF":2.5,"publicationDate":"2023-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48397082","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
Conversion of α-Diazoketones into 1-Bromo-2-alkyl- or 2-arylpent-4-en-2-ols using Tin-Mediated Allylation/Propargylation 使用锡介导的烯丙基化/丙炔基化将α-二唑酮转化为1-溴-2-烷基-或2-芳基戊-4-烯-2-醇
IF 2.5
SynOpen Pub Date : 2023-03-02 DOI: 10.1055/a-2068-5625
S. Biswas, Sipak Joyasawal
{"title":"Conversion of α-Diazoketones into 1-Bromo-2-alkyl- or 2-arylpent-4-en-2-ols using Tin-Mediated Allylation/Propargylation","authors":"S. Biswas, Sipak Joyasawal","doi":"10.1055/a-2068-5625","DOIUrl":"https://doi.org/10.1055/a-2068-5625","url":null,"abstract":"High yielding and mild conditions to prepare of 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols/1-bromo-2-alkyl-or 2-arylpent-4-yn-2-ols from α-diazoketones which involves allylation/propargylation with successive bromide insertion using in-situ generated allyltin bromide/or propargyltin bromide from activated tin metal and allyl/or propargyl bromide.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"161 - 164"},"PeriodicalIF":2.5,"publicationDate":"2023-03-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41939124","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 Calix[4]arene Appended Lactosylated G 1 and Galactosylated G 2 Generation Glycodendrimers using a ‘CuAAC’ Click Approach CuAAC点击法合成杯[4]芳烃连接的乳糖基G1和半乳糖基G2代糖树状大分子
IF 2.5
SynOpen Pub Date : 2023-01-31 DOI: 10.1055/a-2063-4139
Sunil Kumar, Mangal S Yadav, Sumit Kumar Singh, S. Rajkhowa, V. Tiwari
{"title":"Synthesis of Calix[4]arene Appended Lactosylated G 1 and Galactosylated G 2 Generation Glycodendrimers using a ‘CuAAC’ Click Approach","authors":"Sunil Kumar, Mangal S Yadav, Sumit Kumar Singh, S. Rajkhowa, V. Tiwari","doi":"10.1055/a-2063-4139","DOIUrl":"https://doi.org/10.1055/a-2063-4139","url":null,"abstract":"A modular click-approach is applied for the expeditious synthesis of lactose- and galactose-coated calixarene cored G1 and G2 generation glycodendrimers, respectively. The developed calixarene glycodendrimers has been characterized by using extensive spectral analysis including NMR (1H and 13C), MS, IR and SEC data.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"145 - 153"},"PeriodicalIF":2.5,"publicationDate":"2023-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45687802","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 Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy 采用闭合环复合策略合成生物活性大环
IF 2.5
SynOpen Pub Date : 2023-01-31 DOI: 10.1055/s-0042-1751453
N. Jahan, Inul Ansary
{"title":"Synthesis of Bioactive Macrocycles Involving Ring-Closing Metathesis Strategy","authors":"N. Jahan, Inul Ansary","doi":"10.1055/s-0042-1751453","DOIUrl":"https://doi.org/10.1055/s-0042-1751453","url":null,"abstract":"This review reports the synthesis of various bioactive macrocycles, involving ring-closing metathesis as a key step, developed since ca. 2000. These macrocycles exhibited biological activities such as antiviral, antifungal, antibacterial, and anticancer activities, and more. Thus, their syntheses and utilization are essential for both synthetic organic and medicinal chemists.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"209 - 242"},"PeriodicalIF":2.5,"publicationDate":"2023-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47500608","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
Recent Advancements in Triazole-based Click Chemistry in Cancer Drug Discovery and Development 基于三唑的点击化学在癌症药物发现和开发中的最新进展
IF 2.5
SynOpen Pub Date : 2023-01-28 DOI: 10.1055/s-0042-1751452
Arun Kumar, A. Yadav, V. Mishra, Deepak Kumar
{"title":"Recent Advancements in Triazole-based Click Chemistry in Cancer Drug Discovery and Development","authors":"Arun Kumar, A. Yadav, V. Mishra, Deepak Kumar","doi":"10.1055/s-0042-1751452","DOIUrl":"https://doi.org/10.1055/s-0042-1751452","url":null,"abstract":"Triazole-based compounds possess a broad range of activity and can be synthesized using click chemistry. Many new chemotherapeutic agents have been developed in recent years by exploiting click chemistry and these are covered in this review.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"186 - 208"},"PeriodicalIF":2.5,"publicationDate":"2023-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48527999","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
Highly Efficient Synthesis of 3,3-Disubstituted Oxindoles through Direct Oxidative Alkylarylation of N -Arylacrylamides with Simple Alkanes N -芳烯酰胺与简单烷烃直接氧化烷基化高效合成3,3-二取代氧吲哚
IF 2.5
SynOpen Pub Date : 2023-01-26 DOI: 10.1055/s-0042-1751451
Y. Chen, Weihong Song, Zhi Zhou, Ziye Zhang, Kai Liu, Xiaofei Zeng, Xiaoyu Han
{"title":"Highly Efficient Synthesis of 3,3-Disubstituted Oxindoles through Direct Oxidative Alkylarylation of N -Arylacrylamides with Simple Alkanes","authors":"Y. Chen, Weihong Song, Zhi Zhou, Ziye Zhang, Kai Liu, Xiaofei Zeng, Xiaoyu Han","doi":"10.1055/s-0042-1751451","DOIUrl":"https://doi.org/10.1055/s-0042-1751451","url":null,"abstract":"A direct oxidative alkylarylation reaction of N-arylacrylamides with simple alkanes for the synthesis of 3,3-disubstituted oxindoles under metal-free conditions was demonstrated. By using PhI(OAc)2 [(diacetoxy)iodobenzene] as an oxidant, a series of 3,3-disubstituted oxindoles bearing different aryl or alkyl substituents were generated in moderate to excellent chemical yields via a radical-initiated alkylation/cyclization process. The reported method features good functional group tolerance and wide substrate range, and provides an effective method for the preparation of various alkyl substituted 3,3-disubstituted oxindoles.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"154 - 160"},"PeriodicalIF":2.5,"publicationDate":"2023-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41416167","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
Emergent Strategies for Catalytic Enantioselective Direct Thiocyanation and Selenocyanation Reactions 催化对映选择性直接硫氰化和硒氰化反应的紧急策略
IF 2.5
SynOpen Pub Date : 2023-01-24 DOI: 10.1055/a-2041-0188
Floris Buttard, T. Besset
{"title":"Emergent Strategies for Catalytic Enantioselective Direct Thiocyanation and Selenocyanation Reactions","authors":"Floris Buttard, T. Besset","doi":"10.1055/a-2041-0188","DOIUrl":"https://doi.org/10.1055/a-2041-0188","url":null,"abstract":"The publisher announces that this article has been temporarily removed. An edited version will be published under the same DOI as soon as possible. We thank you for your understanding. If you have any questions, please contact am-query@thieme.com.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"117 - 120"},"PeriodicalIF":2.5,"publicationDate":"2023-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41977992","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
A Chitosan Hydrochloride Mediated, Simple and Efficient Approach for the Synthesis of Hydrazones, their in vitro Antimycobacterial Evaluations, and Molecular Modeling Studies (Part III) 壳聚糖盐酸盐介导的简单有效的腙合成方法、体外抗菌评价和分子模型研究（第三部分）
IF 2.5
SynOpen Pub Date : 2023-01-16 DOI: 10.1055/a-2035-6493
Suraj N. Mali, Anima Pandey, B. Thorat
{"title":"A Chitosan Hydrochloride Mediated, Simple and Efficient Approach for the Synthesis of Hydrazones, their in vitro Antimycobacterial Evaluations, and Molecular Modeling Studies (Part III)","authors":"Suraj N. Mali, Anima Pandey, B. Thorat","doi":"10.1055/a-2035-6493","DOIUrl":"https://doi.org/10.1055/a-2035-6493","url":null,"abstract":"A simple, eco-friendly and straightforward synthesis of hydrazones have been devised in the presence of Chitosan Hydrochloride as catalyst in aqueous-ethanol medium at room temperature. The current protocol offers metal-free synthesis, adaptability to large-scaleup, good yields, and quicker reaction time. All synthesized hydrazones (3a-3j) were also depicted good antimycobacterial activity with MICs (minimum inhibitory concentrations) ranging from 3.12-6.25 µg/mL. Compound 3b represented strong binding affinity against M. tuberculosis pantothenate synthetase (pdb id: 3IVX) with a Glide docking score of -8.803 kcal/mol. Molecular dynamics simulation analysis of the complex 3b:3IVX retained good stability over the simulation period of 20 ns.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"102 - 109"},"PeriodicalIF":2.5,"publicationDate":"2023-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48559780","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
Red-Shifting Blue Light Photoredox Catalysis for Organic Synthesis: A Graphical Review 有机合成中红移蓝光光氧化还原催化:图解综述
IF 2.5
SynOpen Pub Date : 2023-01-11 DOI: 10.1055/s-0040-1720060
Logan R. Beck, Katherine Xie, Samantha L. Goldschmid, Stavros K. Kariofillis, C. Joe, Trevor C. Sherwood, Melda Sezen-Edmonds, T. Rovis
{"title":"Red-Shifting Blue Light Photoredox Catalysis for Organic Synthesis: A Graphical Review","authors":"Logan R. Beck, Katherine Xie, Samantha L. Goldschmid, Stavros K. Kariofillis, C. Joe, Trevor C. Sherwood, Melda Sezen-Edmonds, T. Rovis","doi":"10.1055/s-0040-1720060","DOIUrl":"https://doi.org/10.1055/s-0040-1720060","url":null,"abstract":"Photoredox catalysis has revolutionized synthetic chemistry in recent decades. However, the field has traditionally used high-energy blue/ultraviolet light to activate chromophores. High-energy irradiation is associated with several drawbacks (e.g., activation of sensitive functional groups, undesired metal-ligand homolysis, background activation of molecules, and poor penetration), which has led researchers to develop alternative systems with lower energy deep red (DR) or near-infrared (NIR) light. This graphical review provides a concise overview of photophysical principles relevant to photoredox catalysis. Several applications that benefit from low-energy irradiation, such as large-scale batch reactions, photodynamic therapy, biological labeling, and multi-photon excitation are reviewed.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"76 - 87"},"PeriodicalIF":2.5,"publicationDate":"2023-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48919495","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
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