Daniela Fonseca, Ana C. Amorim, Elisabete P. Carreiro, J. Ramalho, G. Hermann, H. Federsel, A. Duarte, A. Burke
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).
{"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}
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
{"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}
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.
{"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}
Sunil Kumar, Mangal S Yadav, Sumit Kumar Singh, S. Rajkhowa, V. Tiwari
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.
{"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}
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.
{"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}
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.
{"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}
Y. Chen, Weihong Song, Zhi Zhou, Ziye Zhang, Kai Liu, Xiaofei Zeng, Xiaoyu Han
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.
{"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}
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.
{"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}
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.
{"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}
Logan R. Beck, Katherine Xie, Samantha L. Goldschmid, Stavros K. Kariofillis, C. Joe, Trevor C. Sherwood, Melda Sezen-Edmonds, T. Rovis
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.
{"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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：