Pub Date : 2024-11-23DOI: 10.1016/j.tetlet.2024.155388
Sumit , Sudipta Nandi , Indrapal Singh Aidhen
Toll-like receptor 4 (TLR4) is a critical component of the innate immune system, recognizing lipopolysaccharide (LPS) from Gram-negative bacteria and triggering immune responses. The activation of TLR4 involves several key steps, including interactions with LPS-binding protein (LBP), CD14, and myeloid differentiation protein 2 (MD-2), culminating in the formation of the (LPS.MD-2 TLR4)2 complex. Structural insights show that LPS acyl chains insert into the hydrophobic pocket of MD-2, driving TLR4 activation. Inspired by this understanding, numerous natural and synthetic compounds have been developed to inhibit TLR4 by targeting the MD-2/TLR4 complex. Eritoran 1, is one such illustration. The conformational flexibility of azepane architecture inspired us to visualize O-alkylated/N-acylated polyhydroxyazepane-based compounds toward this objective. The docking studies and molecular simulation studies supported the rationale. Synthesis of O-alkylated/N-acylated polyhydroxyazepane-based compounds 2-4 (a-h) through a key building block is described herein.
{"title":"Convenient synthesis of O-alkylated/N-acylated polyhydroxyazepane based compounds for modulating MD-2-TLR4 complex formation","authors":"Sumit , Sudipta Nandi , Indrapal Singh Aidhen","doi":"10.1016/j.tetlet.2024.155388","DOIUrl":"10.1016/j.tetlet.2024.155388","url":null,"abstract":"<div><div>Toll-like receptor 4 (TLR4) is a critical component of the innate immune system, recognizing lipopolysaccharide (LPS) from Gram-negative bacteria and triggering immune responses. The activation of TLR4 involves several key steps, including interactions with LPS-binding protein (LBP), CD14, and myeloid differentiation protein 2 (MD-2), culminating in the formation of the (LPS.MD-2 TLR4)<sub>2</sub> complex. Structural insights show that LPS acyl chains insert into the hydrophobic pocket of MD-2, driving TLR4 activation. Inspired by this understanding, numerous natural and synthetic compounds have been developed to inhibit TLR4 by targeting the MD-2/TLR4 complex. Eritoran <strong>1</strong>, is one such illustration. The conformational flexibility of azepane architecture inspired us to visualize <em>O</em>-alkylated/<em>N</em>-acylated polyhydroxyazepane-based compounds toward this objective. The docking studies and molecular simulation studies supported the rationale. Synthesis of <em>O</em>-alkylated/<em>N</em>-acylated polyhydroxyazepane-based compounds <strong>2</strong>-<strong>4</strong> (<strong>a</strong>-<strong>h</strong>) through a key building block is described herein.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155388"},"PeriodicalIF":1.5,"publicationDate":"2024-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142719961","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-22DOI: 10.1016/j.tetlet.2024.155366
He Wu, Yong Wang, Guangguang Yang, Karuppu Selvaraj, Gang Chen
Tetracycline destructases (TDases), a type of TC-inactivating enzymes, inactivate all known TC antibiotics by C11a oxidation, which is considered as a clinical threat. To provide more information on this enzymatic inactivation and oxygenated TCs, we report here a chemical oxidation of Tetracycline and its derivatives at the C11a position using m-CPBA with additives via biomimetic pathways. The structures of the oxygen-containing TCs (2h, 2i) were confirmed by X-ray analysis, and further transformations were performed with oxygen-containing TCs (2e, 2i).
四环素破坏酶（TDases）是四环素类抗生素失活酶的一种，它通过 C11a 氧化作用使所有已知的四环素类抗生素失活，这被认为是一种临床威胁。为了提供更多有关这种酶失活和含氧三环素的信息，我们在此报告利用 m-CPBA 和添加剂通过仿生途径对四环素及其衍生物的 C11a 位进行化学氧化。含氧三氯乙酸的结构（2h、2i）已通过 X 射线分析得到证实，含氧三氯乙酸的进一步转化（2e、2i）也已完成。
{"title":"Biomimetic oxidation of tetracycline and derivatives at C11a","authors":"He Wu, Yong Wang, Guangguang Yang, Karuppu Selvaraj, Gang Chen","doi":"10.1016/j.tetlet.2024.155366","DOIUrl":"10.1016/j.tetlet.2024.155366","url":null,"abstract":"<div><div>Tetracycline destructases (TDases), a type of TC-inactivating enzymes, inactivate all known TC antibiotics by C11a oxidation, which is considered as a clinical threat. To provide more information on this enzymatic inactivation and oxygenated TCs, we report here a chemical oxidation of Tetracycline and its derivatives at the C11a position using <em>m</em>-CPBA with additives via biomimetic pathways. The structures of the oxygen-containing TCs (<strong>2h, 2i</strong>) were confirmed by X-ray analysis, and further transformations were performed with oxygen-containing TCs (<strong>2e</strong>, <strong>2i</strong>).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155366"},"PeriodicalIF":1.5,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702929","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-21DOI: 10.1016/j.tetlet.2024.155373
Jun Ma , Huali Wang , Qingyu Meng , Haoyue Wang , Fangyi Li , Zheng Li
A novel one-step synthesis of valuable 2,4,5-vinylic-trisubstituted oxazoles is described. This reaction, utilizing readily available β,β-dibrominated secondary enamides and terminal alkenes as starting materials, occurs via a ligand-free Palladium-catalyzed cascade intramolecular CO coupling/intermolecular Heck reaction.
本文介绍了一步合成有价值的 2,4,5-乙烯基三取代噁唑的新方法。该反应以现成的 β,β-二溴化仲烯酰胺和末端烯为起始原料，通过无配体钯催化的级联分子内 CO 偶联/分子间 Heck 反应进行。
{"title":"Synthesis of 2,4,5-vinylic-trisubstituted oxazoles via a Palladium-catalyzed cascade coupling reaction","authors":"Jun Ma , Huali Wang , Qingyu Meng , Haoyue Wang , Fangyi Li , Zheng Li","doi":"10.1016/j.tetlet.2024.155373","DOIUrl":"10.1016/j.tetlet.2024.155373","url":null,"abstract":"<div><div>A novel one-step synthesis of valuable 2,4,5-vinylic-trisubstituted oxazoles is described. This reaction, utilizing readily available β,β-dibrominated secondary enamides and terminal alkenes as starting materials, occurs via a ligand-free Palladium-catalyzed cascade intramolecular C<img>O coupling/intermolecular Heck reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155373"},"PeriodicalIF":1.5,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-20DOI: 10.1016/j.tetlet.2024.155386
Sudhir R. Ingale , Ramavath Vinodkumar , Ravindar Kontham
Herein, we report the first stereoselective total synthesis of the eremophilane-type sesquiterpenoid (−)-peniroqueforin C using a chiral-pool strategy. This synthetic route features the use of readily available (S)-(+)-carvone as a chiral building block, Robinson annulation to construct the decalin system, substrate-controlled stereoselective methylation, single-step annulative construction of a tricyclic γ-ylidene-butenolide with concomitant alkene transposition, and direct lactone-to-lactam conversion as key transformations.
{"title":"The first enantioselective total synthesis of the eremophilane-type sesquiterpenoid (−)-peniroqueforin C","authors":"Sudhir R. Ingale , Ramavath Vinodkumar , Ravindar Kontham","doi":"10.1016/j.tetlet.2024.155386","DOIUrl":"10.1016/j.tetlet.2024.155386","url":null,"abstract":"<div><div>Herein, we report the first stereoselective total synthesis of the eremophilane-type sesquiterpenoid (−)-peniroqueforin C using a chiral-pool strategy. This synthetic route features the use of readily available (<em>S</em>)-(+)-carvone as a chiral building block, Robinson annulation to construct the decalin system, substrate-controlled stereoselective methylation, single-step annulative construction of a tricyclic <em>γ</em>-ylidene-butenolide with concomitant alkene transposition, and direct lactone-to-lactam conversion as key transformations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155386"},"PeriodicalIF":1.5,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.tetlet.2024.155384
Hyu Kumazawa, Masahisa Nakada
The Pd-catalyzed cycloisomerization of thiocarbamates with consecutive formation of a quaternary carbon and a sulfide is described. This Pd-catalyzed cascade reaction occurred with both alkylthiocarbamates and arylthiocarbamates, and arylthiocarbamates reacted faster than alkylthiocarbamates. The Pd-catalyzed cycloisomerization can be applied to phenylene- and alkylene-tethered substrates, and thiocarbamate was found to be less reactive than carbamimidothioate. The Pd-catalyzed cycloisomerization can be used to form bridged rings and is expected to be useful for ring construction of nitrogen-containing polycyclic natural products.
{"title":"Palladium-catalyzed cycloisomerization of thiocarbamates with consecutive formation of quaternary carbon and sulfide","authors":"Hyu Kumazawa, Masahisa Nakada","doi":"10.1016/j.tetlet.2024.155384","DOIUrl":"10.1016/j.tetlet.2024.155384","url":null,"abstract":"<div><div>The Pd-catalyzed cycloisomerization of thiocarbamates with consecutive formation of a quaternary carbon and a sulfide is described. This Pd-catalyzed cascade reaction occurred with both alkylthiocarbamates and arylthiocarbamates, and arylthiocarbamates reacted faster than alkylthiocarbamates. The Pd-catalyzed cycloisomerization can be applied to phenylene- and alkylene-tethered substrates, and thiocarbamate was found to be less reactive than carbamimidothioate. The Pd-catalyzed cycloisomerization can be used to form bridged rings and is expected to be useful for ring construction of nitrogen-containing polycyclic natural products.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155384"},"PeriodicalIF":1.5,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.tetlet.2024.155382
Amit Patwa, Chayanika Pegu, Bidisha Paroi, Nitin T. Patil
Over the decades, enantioselective metal/enzyme dual catalysis has emerged as a dynamic area of research in asymmetric synthesis. By leveraging the unique reactivities of metal/enzyme dual catalysis, numerous transformations have been developed, primarily relying on metals such as Pd, Ru, Ir, Fe and Au. Among all transition metals, gold stands out as the catalyst of choice due to its soft π-acidic nature. The π-activation reactivities of gold catalysts have been strategically integrated with enzyme catalysis, thereby leading to highly enantioselective transformations that are unattainable via a single catalyst alone. This review endeavors to provide an overview of the advancements in enantioselective gold/enzyme dual catalysis.
几十年来，对映选择性金属/酶双重催化已成为不对称合成领域中一个充满活力的研究领域。利用金属/酶双催化的独特反应活性，人们开发出了许多转化方法，主要依赖于 Pd、Ru、Ir、Fe 和 Au 等金属。在所有过渡金属中，金因其软π酸性而成为首选催化剂。金催化剂的π-活化反应性已与酶催化进行了战略整合，从而实现了单个催化剂无法实现的高对映选择性转化。本综述旨在概述对映选择性金/酶双重催化方面的进展。
{"title":"Enantioselective gold/enzyme dual catalysis","authors":"Amit Patwa, Chayanika Pegu, Bidisha Paroi, Nitin T. Patil","doi":"10.1016/j.tetlet.2024.155382","DOIUrl":"10.1016/j.tetlet.2024.155382","url":null,"abstract":"<div><div>Over the decades, enantioselective metal/enzyme dual catalysis has emerged as a dynamic area of research in asymmetric synthesis. By leveraging the unique reactivities of metal/enzyme dual catalysis, numerous transformations have been developed, primarily relying on metals such as Pd, Ru, Ir, Fe and Au. Among all transition metals, gold stands out as the catalyst of choice due to its soft <em>π</em>-acidic nature. The <em>π</em>-activation reactivities of gold catalysts have been strategically integrated with enzyme catalysis, thereby leading to highly enantioselective transformations that are unattainable <em>via</em> a single catalyst alone. This review endeavors to provide an overview of the advancements in enantioselective gold/enzyme dual catalysis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155382"},"PeriodicalIF":1.5,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702928","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.tetlet.2024.155385
Dan Yang , Beichen Wang , Zihao Song , Jiahui Tang , Ning Wang , Jun Wang , Yu Wang , Yi-Ming Li
Cell-penetrating peptides (CPP) enable to deliver large biomolecules (proteins, peptides, oligonucleotides, etc.) into cells. An important step for the conjugation of CPPs to target proteins is the acquisition of activated CPPs, however, it requires a multi-step isolation and purification process. Here, we report a facile strategy for the synthesis of activated cell-penetrating peptides via a one-step solid-phase synthesis through the reaction of 5,5′-dithiobis(2-nitrobenzoic acid) (DTNB) with CPP on resins, which can then be treated with a TFA cocktails to directly obtain activated CPP (TNB-CPP). Using this strategy, we successfully obtained activated cyclic cell-penetrating deca-arginine peptide (TNB-cR10) and activated Tat (TNB-Tat) and efficient cytosolic delivery of ubiquitin (Ub) can be achieved by linking it to these CPPs.
{"title":"One-step solid-phase synthesis of activated cell-penetrating peptides for cytosolic delivery of protein","authors":"Dan Yang , Beichen Wang , Zihao Song , Jiahui Tang , Ning Wang , Jun Wang , Yu Wang , Yi-Ming Li","doi":"10.1016/j.tetlet.2024.155385","DOIUrl":"10.1016/j.tetlet.2024.155385","url":null,"abstract":"<div><div>Cell-penetrating peptides (CPP) enable to deliver large biomolecules (proteins, peptides, oligonucleotides, etc.) into cells. An important step for the conjugation of CPPs to target proteins is the acquisition of activated CPPs, however, it requires a multi-step isolation and purification process. Here, we report a facile strategy for the synthesis of activated cell-penetrating peptides via a one-step solid-phase synthesis through the reaction of 5,5′-dithiobis(2-nitrobenzoic acid) (DTNB) with CPP on resins, which can then be treated with a TFA cocktails to directly obtain activated CPP (TNB-CPP). Using this strategy, we successfully obtained activated cyclic cell-penetrating deca-arginine peptide (TNB-cR10) and activated Tat (TNB-Tat) and efficient cytosolic delivery of ubiquitin (Ub) can be achieved by linking it to these CPPs.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155385"},"PeriodicalIF":1.5,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699331","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A water-mediated, chemoenzymatic reaction has been developed for synthesizing various heterocycles. This reported method is compatible with various condensation reactions and multi-component reactions, such as the Biginelli reaction. It offers direct access to benzothiazole, benzimidazole, benzoxazole, quinazolinone, and pyrimidines using straightforward reaction conditions, adhering to green chemistry principles.
{"title":"Candida antarctica lipase B catalyzed condensation reactions: Water mediated chemo-enzymatic synthesis of different heterocycles","authors":"Satyaveni Malasala , Anusha Polomani , Jitendra Gour , Srinivas Nanduri","doi":"10.1016/j.tetlet.2024.155371","DOIUrl":"10.1016/j.tetlet.2024.155371","url":null,"abstract":"<div><div>A water-mediated, chemoenzymatic reaction has been developed for synthesizing various heterocycles. This reported method is compatible with various condensation reactions and multi-component reactions, such as the Biginelli reaction. It offers direct access to benzothiazole, benzimidazole, benzoxazole, quinazolinone, and pyrimidines using straightforward reaction conditions, adhering to green chemistry principles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155371"},"PeriodicalIF":1.5,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.tetlet.2024.155370
Jia-Wei Li , Xiao-Hong Chen , Wenke Dong , Yuhan Li , Xiaobing Liu , Guanglu Liu , Hui Zhang , Chunjie Wang , Yue-Jin Liu
Naphthyl-containing skeleton is well known as building blocks in bioactive molecules, organic catalyst and functional materials. Chemists have put massive efforts and remarkable achievements have been made in site-selective diversified derivatizations of naphthalenes. This digest review presents the recent and inspiring results in this high-profile area beyond 2020.
{"title":"Recent advances in site-selective CH functionalization of naphthalenes: An update 2020–2024","authors":"Jia-Wei Li , Xiao-Hong Chen , Wenke Dong , Yuhan Li , Xiaobing Liu , Guanglu Liu , Hui Zhang , Chunjie Wang , Yue-Jin Liu","doi":"10.1016/j.tetlet.2024.155370","DOIUrl":"10.1016/j.tetlet.2024.155370","url":null,"abstract":"<div><div>Naphthyl-containing skeleton is well known as building blocks in bioactive molecules, organic catalyst and functional materials. Chemists have put massive efforts and remarkable achievements have been made in site-selective diversified derivatizations of naphthalenes. This digest review presents the recent and inspiring results in this high-profile area beyond 2020.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155370"},"PeriodicalIF":1.5,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702927","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-16DOI: 10.1016/j.tetlet.2024.155383
Ankita Garg, Teesha Thakral, Rajat Dhiman, Aman Bhalla
β-Lactams have long been a cornerstone in the treatment of various bacterial infections, largely due to their unique structure–activity relationship with pathogenic bacteria. Significant efforts have been devoted in the literature to the development of novel β-lactam compounds and their subsequent medicinal evaluation. Moreover, the structural diversity in β-lactam derivatives has garnered significant interest in medicinal arena. Therefore, in this review thoroughly discusses the impact of structural diversity on various medicinal applications, which can be achieved through multiple synthetic approaches, including stereoselective reactions, heterocyclic fusion, regioselective modifications, and metal-catalyzed transformations. Additionally, the occurrence of functional groups such as electron-donating or electron-withdrawing groups in structurally diverse β-lactam scaffolds has been explored to assess their medicinal impact. Furthermore, β-lactam compounds have increasingly attracted interest in medicinal chemistry because of their many other remarkable biological activities. Through the analysis of stereoselectivity, heterocyclic motifs, and the impacts of functional groups, we highlight the compounds noteworthy for medicinal applications, including anti-bacterial, anti-fungal, anti-cancer, anti-oxidant, anti-diabetic, anti-viral, anti-tubercular, anti-inflammatory, analgesic and anti-malarial activity. Owing to these captivating pharmacological properties, this review provides a comprehensive update on the varied medicinal applications of β-lactam scaffolds, emphasizing a wide range of examples from 2020 to 2024.
{"title":"An insights into structural diversity of β-lactam scaffold towards varied medicinal applications: A comprehensive update (2020–2024)","authors":"Ankita Garg, Teesha Thakral, Rajat Dhiman, Aman Bhalla","doi":"10.1016/j.tetlet.2024.155383","DOIUrl":"10.1016/j.tetlet.2024.155383","url":null,"abstract":"<div><div>β-Lactams have long been a cornerstone in the treatment of various bacterial infections, largely due to their unique structure–activity relationship with pathogenic bacteria. Significant efforts have been devoted in the literature to the development of novel β-lactam compounds and their subsequent medicinal evaluation. Moreover, the structural diversity in β-lactam derivatives has garnered significant interest in medicinal arena. Therefore, in this review thoroughly discusses the impact of structural diversity on various medicinal applications, which can be achieved through multiple synthetic approaches, including stereoselective reactions, heterocyclic fusion, regioselective modifications, and metal-catalyzed transformations. Additionally, the occurrence of functional groups such as electron-donating or electron-withdrawing groups in structurally diverse β-lactam scaffolds has been explored to assess their medicinal impact. Furthermore, β-lactam compounds have increasingly attracted interest in medicinal chemistry because of their many other remarkable biological activities. Through the analysis of stereoselectivity, heterocyclic motifs, and the impacts of functional groups, we highlight the compounds noteworthy for medicinal applications, including anti-bacterial, anti-fungal, anti-cancer, anti-oxidant, anti-diabetic, anti-viral, anti-tubercular, anti-inflammatory, analgesic and anti-malarial activity. Owing to these captivating pharmacological properties, this review provides a comprehensive update on the varied medicinal applications of β-lactam scaffolds, emphasizing a wide range of examples from 2020 to 2024.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155383"},"PeriodicalIF":1.5,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699271","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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