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Phosphazene-Catalyzed Cascade Esterification/Stereoselective Aza-Michael Addition of Chiral β-Trifluoromethyl-α,β-unsaturated N-Acylated Oxazolidin-2-ones 磷杂环催化的手性 β-三氟甲基-α,β-不饱和 N-酰化恶唑烷-2-酮的级联酯化/半选择性 Aza-Michael 加成反应
Synlett Pub Date : 2024-07-16 DOI: 10.1055/a-2364-6119
Sasirome Racochote, C. Kuhakarn, Pawaret Leowanawat, V. Reutrakul, Darunee Soorukram
{"title":"Phosphazene-Catalyzed Cascade Esterification/Stereoselective Aza-Michael Addition of Chiral β-Trifluoromethyl-α,β-unsaturated N-Acylated Oxazolidin-2-ones","authors":"Sasirome Racochote, C. Kuhakarn, Pawaret Leowanawat, V. Reutrakul, Darunee Soorukram","doi":"10.1055/a-2364-6119","DOIUrl":"https://doi.org/10.1055/a-2364-6119","url":null,"abstract":"Upon treatment of chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones with a range of alcohols using phosphazene base as a catalyst, the unexpected cascade esterification/stereoselective aza-Michael addition was observed. The reactions proceeded with high diastereoselectivities (up to ≧ 99:1) to give a series of enantioenriched aza-Michael addition products in good to high yields. The structure and stereochemistry of the representative aza-Michael adduct were confirmed by X-ray analysis. The plausible mechanism was proposed on the basis of the experimental results. The synthetic transformations of chiral aza-Michael addition products were also demonstrated highlighting the synthetic application of the present work.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"11 47","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141640525","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
N-heterocyclic carbene-catalyzed reassembling of dibenzyl ethers: facile access to α-hydroxy ketones N-杂环碳烯催化的二苄基醚再组装:轻松获得α-羟基酮
Synlett Pub Date : 2024-07-16 DOI: 10.1055/a-2367-2572
Zheyao Li, Lei Ju, Ruipeng Bao, Xinbo Lin, Teng Wang, Xinhong Yu
{"title":"N-heterocyclic carbene-catalyzed reassembling of dibenzyl ethers: facile access to α-hydroxy ketones","authors":"Zheyao Li, Lei Ju, Ruipeng Bao, Xinbo Lin, Teng Wang, Xinhong Yu","doi":"10.1055/a-2367-2572","DOIUrl":"https://doi.org/10.1055/a-2367-2572","url":null,"abstract":"A novel one-pot cascade process of oxidation-initiated N-heterocyclic carbene-catalyzed reintegration of dibenzyl ethers has been developed for the first time. This protocol allows straightforward access to α-hydroxy ketones from dibenzyl ethers. It is noteworthy that the present method is the first attempt to synthesize benzoin by utilization of dibenzyl ethers.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"5 10","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141642130","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
Erratum: Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines 勘误:通过酮与邻苯二胺的分子间环化/脱氢反应电合成喹喔啉类化合物
Synlett Pub Date : 2024-07-08 DOI: 10.1055/s-0043-1774966
Yi Tao, Jiahui Zhang, Yangyang Hu, Huiying Liu, Jingwen Sun, Lei Liu
{"title":"Erratum: Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines","authors":"Yi Tao, Jiahui Zhang, Yangyang Hu, Huiying Liu, Jingwen Sun, Lei Liu","doi":"10.1055/s-0043-1774966","DOIUrl":"https://doi.org/10.1055/s-0043-1774966","url":null,"abstract":"","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 604","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141669492","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
Stereoselective Synthesis of Polyketide Segments of Nemamide A and Euglenatides D-E 内酰胺 A 和丁香酸 D-E 的多酮苷段的立体选择性合成
Synlett Pub Date : 2024-07-07 DOI: 10.1055/a-2361-3510
Himangshu Sharma, Sujan Paul, R. Goswami
{"title":"Stereoselective Synthesis of Polyketide Segments of Nemamide A and Euglenatides D-E","authors":"Himangshu Sharma, Sujan Paul, R. Goswami","doi":"10.1055/a-2361-3510","DOIUrl":"https://doi.org/10.1055/a-2361-3510","url":null,"abstract":"A convergent strategy for the stereoselective synthesis of polyketide segments of hybrid natural products nemamide A and euglenatides D-E has been developed for the first time. The salient features of this gram scale synthesis include Trost-Rychnovsky alkyne rearrangement, HWE olefination, regioselective epoxide ring opening, Prins/Ritter cyclization and subsequent reductive cleavage of the substituted THP ring. The optimized route is modular and could be tunable to access the other polyketide counterparts of these families of metabolites.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 15","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141670196","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
Development of new N-(4-((7-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)oxy)-3-fluorophenyl)benzenesulfonamide analogues: Exploring anticancer potential via MerTK inhibition 开发新的 N-(4-((7-氯-5-甲基吡咯并[2,1-f][1,2,4]三嗪-4-基)氧基)-3-氟苯基)苯磺酰胺类似物:通过抑制 MerTK 探索抗癌潜力
Synlett Pub Date : 2024-07-04 DOI: 10.1055/a-2360-6586
Balaji Dashrath Sathe, Meenakshi Meenakshi, Yogesh Murti, Madhav Shivaji Mane, Sarvesh Kumar Pandey, Shriya Mahajan, Pramod Rawat, Harsimrat Kandhari, K. Goel, A. Dwivedi, S. V. Rathod
{"title":"Development of new N-(4-((7-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)oxy)-3-fluorophenyl)benzenesulfonamide analogues: Exploring anticancer potential via MerTK inhibition","authors":"Balaji Dashrath Sathe, Meenakshi Meenakshi, Yogesh Murti, Madhav Shivaji Mane, Sarvesh Kumar Pandey, Shriya Mahajan, Pramod Rawat, Harsimrat Kandhari, K. Goel, A. Dwivedi, S. V. Rathod","doi":"10.1055/a-2360-6586","DOIUrl":"https://doi.org/10.1055/a-2360-6586","url":null,"abstract":"Mer proto-oncogene tyrosine-protein kinase (MerTK), a part of TAM (TYRO3, AXL and MerTK) family, is directly correlated with metastasis and various types of cancers. The inhibition of this receptor tyrosine kinase is one of the promising therapeutic strategies, as chemotherapy has higher efficacy. Considering the pharmacophoric features of the active domain of MerTK and structural characteristics of investigational drug, BMS794833, we have designed new N-(4-((7-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)oxy)-3-fluorophenyl)benzenesulfonamide analogues (BDS-001 to BDS-005). In cytotoxic studies, BDS-001 displayed significantly higher cytotoxicity than cisplatin. It showed IC50 values of 2.09 µM, 1.96 µM and 3.08 µM against A549, MCF-7 and MDA-MB-231 cancer cell lines, respectively. In DMPK studies, BDS-001 was most stable and displayed moderate MerTK inhibitory potential. Molecular docking studies were performed to corroborate the MerTK inhibition, and BDS-001 was gave the most significant docking score (-12.33 Kcal/mol). Docking interactions demonstrated that imine and amine group of 3-chloropyridine moiety of BMS794833 formed a hydrogen bond with main chain of ATP pocket residue Met674, while oxygen atoms of 4-oxo-1,4-dihydropyridine-3-carboxamide moiety established hydrogen bonds with Lys619 and Asp741 amino acid residues of allosteric pocket of MerTK protein. These promising results are evident that N-(4-((7-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)oxy)-3-fluorophenyl)benzenesulfonamide pharmacophore can provide potential insights in development of new MerTK inhibitors.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 16","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141679582","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
Triton B Catalyzed Rapid and Mild Synthetic Protocol for both Henry Reaction of Isatin and Michael Reaction of Chalcone with Nitroalkane 以 Triton B 为催化剂,快速、温和地合成靛红的 Henry 反应和查尔酮与硝基烷烃的迈克尔反应的方法
Synlett Pub Date : 2024-04-23 DOI: 10.1055/s-0043-1774862
Eeshwaraiah Begari, Mrinal Talukdar, Nasreen Islam, Akanksha Mishra, A. Dave
{"title":"Triton B Catalyzed Rapid and Mild Synthetic Protocol for both Henry Reaction of Isatin and Michael Reaction of Chalcone with Nitroalkane","authors":"Eeshwaraiah Begari, Mrinal Talukdar, Nasreen Islam, Akanksha Mishra, A. Dave","doi":"10.1055/s-0043-1774862","DOIUrl":"https://doi.org/10.1055/s-0043-1774862","url":null,"abstract":"A highly efficient and general synthetic protocol for both Henry and Michael reactions was developed using metal-free catalyst Triton B (benzyltrimethylammonium hydroxide) and isatins and chalcones, respectively. This methodology is inexpensive, the reagents are easy to handle, and the approach offers wide functional group tolerance of isatins and chalcones. The base catalyst Triton B is less toxic, recyclable, and reusable. This efficient method reduces reaction times, minimizes reagent excess, avoids chromatography, and is aligned with sustainable chemistry principles, offering eco-friendly applications in diverse industries.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"55 16","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140667005","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
Organophotocatalytic or Electrophotocatalytic Reduction and Functionalization Reactions with a Thioxanthone-TfOH Complex Catalyst 使用硫黄酮-TfOH 复合物催化剂进行有机光催化或电光催化还原和功能化反应
Synlett Pub Date : 2024-04-23 DOI: 10.1055/a-2312-5896
Wen-Jie Kang, Yanbin Zhang, Hao Guo
{"title":"Organophotocatalytic or Electrophotocatalytic Reduction and Functionalization Reactions with a Thioxanthone-TfOH Complex Catalyst","authors":"Wen-Jie Kang, Yanbin Zhang, Hao Guo","doi":"10.1055/a-2312-5896","DOIUrl":"https://doi.org/10.1055/a-2312-5896","url":null,"abstract":"Thioxanthone has long been a prominent catalyst in the field of photocatalysis, owing to its high triplet energy and long triplet lifetime that render it suitable for energy transfer reactions. However, its low oxidation potential and short singlet lifetime have posed challenges in employing it for electron transfer reactions. This account summarizes our efforts in developing a potent and long-lived thioxanthone-TfOH complex (9-HTXTF) catalyst, and its application in some energy-demanding redox transformations such as organophotocatalytic or electrophotocatalytic reduction and functionalization reactions.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"128 47","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140668887","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
Unexpected one-pot synthesis of 3-cinnamoyl-3-hydroxyphthalide derivatives 意想不到的 3-肉桂酰基-3-羟基苯酞衍生物的单锅合成
Synlett Pub Date : 2024-04-23 DOI: 10.1055/a-2312-0444
Intouch Rakchaya, Phanida Thongaram, Sengchan Saiyalard, Kredmanee Yimnoi, W. Wattanathana, Nutthawat Chuanopparat, P. Ngernmeesri
{"title":"Unexpected one-pot synthesis of 3-cinnamoyl-3-hydroxyphthalide derivatives","authors":"Intouch Rakchaya, Phanida Thongaram, Sengchan Saiyalard, Kredmanee Yimnoi, W. Wattanathana, Nutthawat Chuanopparat, P. Ngernmeesri","doi":"10.1055/a-2312-0444","DOIUrl":"https://doi.org/10.1055/a-2312-0444","url":null,"abstract":"A new and simple method to prepare 3-cinnamoyl-3-hydroxyphthalide derivatives from 2-hydroxy-3-methyl-1,4-naphthoquinone and substituted benzaldehydes was unexpectedly uncovered. The reaction was conveniently performed in DMSO at 100 ⁰C with K3PO4 as a base and AlCl3 as a catalyst. We proposed that the products occurred via a cascade process involving nucleophilic addition followed by demethylation and rearrangement. The products were typically obtained in moderate to good yields. The highest yield (95%) was obtained when the reaction of 2-bromobenzaldehyde was performed for 24 hours. X-ray crystallography of the product derived from 2-fluorobenzaldehyde unequivocally confirmed the structures of the hydroxyphthalide derivatives.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"87 10","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140670611","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
A Personal Account from Inside Keith Fagnou’s Research Laboratory 基思-法格努研究实验室内部的亲身经历
Synlett Pub Date : 2024-04-23 DOI: 10.1055/s-0043-1774827
Louis-Charles Campeau
{"title":"A Personal Account from Inside Keith Fagnou’s Research Laboratory","authors":"Louis-Charles Campeau","doi":"10.1055/s-0043-1774827","DOIUrl":"https://doi.org/10.1055/s-0043-1774827","url":null,"abstract":"<jats:p />","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"24 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140665726","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
From Protein Structures to Functional Biomimetics 从蛋白质结构到功能生物仿生学
Synlett Pub Date : 2024-04-17 DOI: 10.1055/a-2308-1795
Canan Durukan, T. Grossmann
{"title":"From Protein Structures to Functional Biomimetics","authors":"Canan Durukan, T. Grossmann","doi":"10.1055/a-2308-1795","DOIUrl":"https://doi.org/10.1055/a-2308-1795","url":null,"abstract":"The development of complex molecular scaffolds with defined folding properties represents a central challenge in chemical research. Proteins are natural scaffolds defined by a hierarchy of structural complexity and have evolved to manifest unique functional characteristics e.g., molecular recognition capabilities that facilitate the binding of target molecules with high affinity and selectivity. Utilizing these features, proteins have been used as a starting point for the design of synthetic foldamers, enhanced biocatalysts as well as bioactive reagents in drug discovery. In this account, we describe the strategies used in our group to stabilize protein folds, ranging from the constraint of bioactive peptide conformations to chemical protein engineering. We discuss the evolution of peptides into peptidomimetics to inhibit protein-protein and protein-nucleic acid interactions, and the selective chemical modification of proteins to enhance their properties for biotechnological applications. The reported peptide- and proteomimetic structures cover a broad range of molecular size and they highlight the importance of structure stabilization for the design of functional biomimetics.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":" 33","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140692441","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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