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Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition 通过叠氮-炔烃环加成法合成具有生物活性的 1,2,3-三唑融合大环
IF 2.5
SynOpen Pub Date : 2024-01-04 DOI: 10.1055/a-2212-0996
{"title":"Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition","authors":"","doi":"10.1055/a-2212-0996","DOIUrl":"https://doi.org/10.1055/a-2212-0996","url":null,"abstract":"A systematic highlight of syntheses reported since 2006 of 1,2,3-triazole-fused macrocycles possessing biological activities such as anticancer, antibacterial, antiviral, anti-inflammatory and antilarval action, is presented in this review. The well-renowned Cu-catalyzed azide-alkyne cycloaddition reaction was noted to be highly efficient and is one the most common methods utilized by scientists for the synthesis of 1,4-disubstituted triazole-fused macrocycles, whereas Ru-catalyzed cycloaddition is common for the formation of 1,5-disubstituted bioactive triazoles. This review would thus be extremely beneficial for both synthetic organic and medicinal chemists.1 Introduction2 Anticancer Derivatives3 Antibacterial Derivatives4 Derivatives with Dual Activity5 Antilarval Derivatives6 Anti-inflammatory Derivatives7 Antiviral Derivatives8 Anti-trypanosomal Derivatives9 Derivatives with Miscellaneous Activities10 Conclusion","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139105337","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 Propellane-Type 5/5/6-Tricyclic System via Tandem-Metathesis: A New Approach to Quadranoid Skeleton 通过串联甲基化反应合成丙烷型 5/5/6 三环系统：四面体骨架的新方法
IF 2.5
SynOpen Pub Date : 2023-12-28 DOI: 10.1055/a-2236-0803
S. Kotha, R. Keesari
{"title":"Synthesis of Propellane-Type 5/5/6-Tricyclic System via Tandem-Metathesis: A New Approach to Quadranoid Skeleton","authors":"S. Kotha, R. Keesari","doi":"10.1055/a-2236-0803","DOIUrl":"https://doi.org/10.1055/a-2236-0803","url":null,"abstract":"We disclose a useful synthetic study to prepare a propellane-type 5/5/6-tricyclic system which is present in diquinane-based natural products such as quadrone, terrecyclic acid A, terrecyclol, etc. The present methodology involves LDA-mediated regio- and stereoselective allylation, and tandem-metathesis as key steps. The target molecules were assembled in just two steps starting from a readily available building block, 3β-vinyl-tricyclic ketone, which is prepared from endo-dicyclopentadiene-1-one. All the compounds prepared here are characterized by NMR data analysis and/or chemical methods. The synthetic studies demonstrated here are useful in the synthesis of quadronoid type of natural products.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139150903","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
Oxidation of Alcohols to Aldehydes and Ketones Using a Catalytic Pairing of a Nitroxide and Nitric Acid 利用氧化氮和硝酸的催化配对将醇氧化成醛和酮
IF 2.5
SynOpen Pub Date : 2023-12-21 DOI: 10.1055/a-2217-9577
Manisha Sharma, Arturo León Sandoval, Nicholas E. Leadbeater
{"title":"Oxidation of Alcohols to Aldehydes and Ketones Using a Catalytic Pairing of a Nitroxide and Nitric Acid","authors":"Manisha Sharma, Arturo León Sandoval, Nicholas E. Leadbeater","doi":"10.1055/a-2217-9577","DOIUrl":"https://doi.org/10.1055/a-2217-9577","url":null,"abstract":"<p>A methodology for the oxidation of alcohols to aldehydes and ketones is presented. The approach employs catalytic quantities of a nitroxide and nitric acid, with no additives or metal catalysts being required. It proves effective for a range of aromatic, heteroaromatic, and aliphatic alcohol substrates, the desired products being formed in good to excellent yield. In the case of primary alcohols, the oxidation can be stopped at the aldehyde without concomitant formation of the corresponding carboxylic acid.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139028221","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
Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study 低分子量超分子阿洛贝图林、环己醇或十一烷醇添加的 1,2,3 三唑基凝胶剂：合成与分子动力学模拟研究
IF 2.5
SynOpen Pub Date : 2023-12-18 DOI: 10.1055/s-0040-1720100
Victoria Lipson, Oleg Zhikol, Svetlana Shishkina, Alexander Semenenko, Karina Kulyk, Pavel Mateychenko, Vladimir Musatov, Alexander Mazepa, Vladimir Vakula, Alexander Borisov, Alexander Kyrychenko
{"title":"Low Molecular Weight Supramolecular Allobetuline-, Cyclohexanol-, or Undecanol-Appended 1,2,3-Triazole-Based Gelators: Synthesis and Molecular Dynamics Simulation Study","authors":"Victoria Lipson, Oleg Zhikol, Svetlana Shishkina, Alexander Semenenko, Karina Kulyk, Pavel Mateychenko, Vladimir Musatov, Alexander Mazepa, Vladimir Vakula, Alexander Borisov, Alexander Kyrychenko","doi":"10.1055/s-0040-1720100","DOIUrl":"https://doi.org/10.1055/s-0040-1720100","url":null,"abstract":"<p>Three novel isomeric supramolecular allobetuline-appended 1,2,3-triazole-based potential gelators and two model compounds with cyclohexanol or undecanol fragments in the structure instead of the triterpenoid platform were synthesized. Their ability to form gels in different solvents was studied experimentally and computationally by molecular dynamics simulations and quantum chemical calculations. We found that the gelling ability of such compounds is driven by the binding energy of intermolecular tail substituent interactions. The less significant factor is the molecule unfolding in a solvent, providing that the gelling substance is actually soluble. Preferred unfolded conformations were identified by classical molecular dynamics simulation and suggested the most prospective 1,2,3-triazole-based potential gelators.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138745884","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 Developments in the Detection of Zn2+ Ions Using Schiff Base Probes 使用希夫碱探针检测 Zn2+ 离子的最新进展
IF 2.5
SynOpen Pub Date : 2023-12-18 DOI: 10.1055/a-2211-2692
Ram Kumar, Bholey Singh, Shwetank Shashi Pandey, Balaram Pani
{"title":"Recent Developments in the Detection of Zn2+ Ions Using Schiff Base Probes","authors":"Ram Kumar, Bholey Singh, Shwetank Shashi Pandey, Balaram Pani","doi":"10.1055/a-2211-2692","DOIUrl":"https://doi.org/10.1055/a-2211-2692","url":null,"abstract":"<p>In the past few decades, zinc has attracted great attention from the scientific community due to its supreme importance in living organisms. Zinc is a trace element that is vitally important to all living organisms and it plays an important role in the immune system, wound healing, growth, and division. Therefore, the development and advancement of simple, efficient, selective, and inexpensive chemosensors for the determination of Zn<sup>2+</sup> is a paramount prerequisite. Chemosensors have unique properties that are used for the specific and selective determination of several metal ions. This review summarizes the Schiff base chemosensors designed and synthesized by several research groups from the year 2018. The interaction of these probes with zinc metal ions has also been discussed briefly in this review. Furthermore, the comparison of detection limits of these probes demonstrated that the Schiff base probe possessing two benzothiazole moieties exhibits the lowest detection limit (0.00028 μM), indicating it to be the lead compound in the determination of Zn<sup>2+</sup> ions in the near future.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138741013","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
tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes 叔丁氧羰基介导的 α-季均苯甲醛原醛脱羰基反应
IF 2.5
SynOpen Pub Date : 2023-12-18 DOI: 10.1055/a-2231-3108
Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco
{"title":"tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes","authors":"Ben Stokes, Xiaofeng Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco","doi":"10.1055/a-2231-3108","DOIUrl":"https://doi.org/10.1055/a-2231-3108","url":null,"abstract":"\u0000 Tert-butoxide mediates the Haller–Bauer-type (protodeformylative) decarbonylation of readily accessed α-quaternary homobenzaldehydes and related compounds at room temperature, generating cumene products. Both geminal dialkyl and geminal diaryl substituents are tolerated. Gem-dimethyls are sufficient for decarbonylation of polycyclic arenyl substrates whereas monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for significant decarbonylation.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138963761","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
New Synthesis of 3-Aminohydantoins via Condensation of Hydrazines with Isocyanates Derived from α-Amino Esters 通过肼与α-氨基酯衍生的异氰酸酯缩合合成 3-氨基海因的新方法
IF 2.5
SynOpen Pub Date : 2023-12-11 DOI: 10.1055/a-2217-6821
Houda Bouchnak, Thierry Ollevier, Jamil Kraïem
{"title":"New Synthesis of 3-Aminohydantoins via Condensation of Hydrazines with Isocyanates Derived from α-Amino Esters","authors":"Houda Bouchnak, Thierry Ollevier, Jamil Kraïem","doi":"10.1055/a-2217-6821","DOIUrl":"https://doi.org/10.1055/a-2217-6821","url":null,"abstract":"<p>A new, simple, and efficient method for the synthesis of 3-aminohydantoins was reported in two steps, starting from the corresponding <i>\u0000<sc>l</sc>\u0000</i>-amino esters. Commercially available α-amino esters were converted into the corresponding isocyanate derivatives, which were then subjected to the condensation reaction with hydrazine hydrate and arylhydrazines, in the presence of DMAP and DIPEA. This method provides the corresponding 3-aminohydantoins in moderate and good yields under a simple and practical protocol.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138575964","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
Gum Acacia Stabilized Ag-TiO2 and Ag-SiO2: Sustainable Nanocatalysts for Direct and Convenient Synthesis of 5-Substituted 1H-tetrazoles 金合木稳定的Ag-TiO2和Ag-SiO2:直接和方便合成5-取代1h -四唑的可持续纳米催化剂
IF 2.5
SynOpen Pub Date : 2023-11-23 DOI: 10.1055/s-0042-1751511
Supriya Prakash, Bojja Sreedhar, N. V. S. Naidu
{"title":"Gum Acacia Stabilized Ag-TiO2 and Ag-SiO2: Sustainable Nanocatalysts for Direct and Convenient Synthesis of 5-Substituted 1H-tetrazoles","authors":"Supriya Prakash, Bojja Sreedhar, N. V. S. Naidu","doi":"10.1055/s-0042-1751511","DOIUrl":"https://doi.org/10.1055/s-0042-1751511","url":null,"abstract":"<p>We describe the use of biocompatible gum acacia (GA)-assembled Ag-TiO<sub>2</sub> and Ag-SiO<sub>2</sub> nanostructures as effective heterogeneous catalysts for the synthesis of 5-substituted 1<i>H</i>-tetrazoles through the traditional [3+2] cycloaddition of aryl nitriles with sodium azides. Characterization of the prepared catalysts employing TEM, XPS, FE-SEM, FT-IR, XRD, and TGA-DTG reveals silver nanoparticles encapsulated in the GA matrix amidst modified nano titania or silica. A variety of structurally divergent aryl nitriles were converted into the corresponding tetrazoles in a short reaction time. Other advantages include low catalytic load, easy handling of catalyst, limited use of toxic reagents, and desirable conversion yields, making this protocol a viable and practical alternative for this cyclization. The catalysts can be easily recovered and reused over multiple cycles without significant loss of catalytic activity.</p> ","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2023-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138524259","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 Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview 过渡金属催化交叉偶联反应的十年探索:综述
SynOpen Pub Date : 2023-11-01 DOI: 10.1055/s-0040-1720096
Anil Kumar, Saurav Kumar, Jyoti Jyoti, Deepak Gupta, Gajendra Singh
{"title":"A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview","authors":"Anil Kumar, Saurav Kumar, Jyoti Jyoti, Deepak Gupta, Gajendra Singh","doi":"10.1055/s-0040-1720096","DOIUrl":"https://doi.org/10.1055/s-0040-1720096","url":null,"abstract":"Abstract During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date. 1 Introduction 2 Pd-Catalyzed Reactions 2.1 C–C Cross-Coupling Reactions 2.2 C–N Cross-Coupling Reactions 2.3 C–P Cross-Coupling Reactions 3 Ni-Catalyzed Cross-Coupling Reactions 3.1 C–C Cross-Coupling Reactions 4 Cu-Catalyzed Cross-Coupling Reactions 4.1 C–C Cross-Coupling Reactions 4.2 C–O Cross-Coupling Reactions 4.2 C–N Cross-Coupling Reactions 4.4 C–P Cross-Coupling Reactions 4.5 C–Se Cross-Coupling Reactions 4.6 C–S Cross-Coupling Reactions 5 Fe-Catalyzed Reactions 5.1 C–C Cross-Coupling Reactions 5.2 C–S Cross-Coupling Reactions 6 Co-Catalyzed Reactions 7 Transition-Metal Nanoparticle-Promoted Reactions 7.1 Pd Nanoparticles 7.2 Cu Nanoparticles 8 Miscellaneous Reactions 9 Perspectives and Future Directions","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135715619","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
The Catalyst’s Companion: N,N′-Dicyclohexylcarbodiimide (DCC) in Action 催化剂的伙伴:N,N ' -二环己基碳二亚胺(DCC)的作用
SynOpen Pub Date : 2023-11-01 DOI: 10.1055/s-0042-1751500
Pooja A. Chawla, Arshdeep Singh, Anjali Sharma
{"title":"The Catalyst’s Companion: N,N′-Dicyclohexylcarbodiimide (DCC) in Action","authors":"Pooja A. Chawla, Arshdeep Singh, Anjali Sharma","doi":"10.1055/s-0042-1751500","DOIUrl":"https://doi.org/10.1055/s-0042-1751500","url":null,"abstract":"Abstract","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135373129","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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