Current organic synthesis最新文献

{"title":"Green Approach Toward Triazole Forming Reactions for Developing Anticancer Drugs.","authors":"Shiva K Rastogi, Veronica C Ciliberto, Monica Z Trevino, Brooke A Campbell, William J Brittain","doi":"10.2174/1570179420666230508125144","DOIUrl":"10.2174/1570179420666230508125144","url":null,"abstract":"<p><p>Compounds containing triazole have many significant applications in the dye and ink industry, corrosion inhibitors, polymers, and pharmaceutical industries. These compounds possess many antimicrobial, antioxidant, anticancer, antiviral, anti-HIV, antitubercular, and anticancer activities. Several synthetic methods have been reported for reducing time, minimizing synthetic steps, and utilizing less hazardous and toxic solvents and reagents to improve the yield of triazoles and their analogues synthesis. Among the improvement in methods, green approaches towards triazole forming biologically active compounds, especially anticancer compounds, would be very important for pharmaceutical industries as well as global research community. In this article, we have reviewed the last five years of green chemistry approaches on click reaction between alkyl azide and alkynes to install 1,2,3-triazole moiety in natural products and synthetic drug-like molecules, such as in colchicine, flavanone cardanol, bisphosphonates, thiabendazoles, piperazine, prostanoid, flavonoid, quinoxalines, C-azanucleoside, dibenzylamine, and aryl-azotriazole. The cytotoxicity of triazole hybrid analogues was evaluated against a panel of cancer cell lines, including multidrug-resistant cell lines.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"380-420"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9800923","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}

{"title":"Iodoxybenzoic Acid (IBX) in Organic Synthesis: A Septennial Review.","authors":"Ravi Varala, Vittal Seema, Mohammed Mujahid Alam, Narsimhaswamy Dubasi, Rama Devi Vummadi","doi":"10.2174/0115701794263252230924074035","DOIUrl":"10.2174/0115701794263252230924074035","url":null,"abstract":"<p><p>This study reviews the oxidative applications of 2-iodoxybenzoic acid (IBX) in organic synthesis, focusing on C-H functionalization, hetero-hetero bond formations, ring cleavage reactions, dehydrogenation, heterocyclic ring formations, and some miscellaneous reactions in a comprehensive and critical way. It compiles the literature starting from mid-2015 to date.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"607-664"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49675461","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}

{"title":"Recent Progress on Synthesis of Functionalized 1,5-Disubstituted Triazoles.","authors":"Manoj K Jaiswal, Abhishek Gupta, Faisal J Ansari, Vinay K Pandey, Vinod K Tiwari","doi":"10.2174/1570179420666230418123350","DOIUrl":"10.2174/1570179420666230418123350","url":null,"abstract":"<p><p>Immediately after the invention of 'Click Chemistry' in 2002, the regioselective 1,2,3- triazole scaffolds resulted from respective organic azides and terminal alkynes under Cu(I) catalysis have been well recognized as the functional heterocyclic core at the centre of modern organic chemistry, medicinal chemistry, and material sciences. This CuAAC reaction has several notable features including excellent regioselectivity, high-to-excellent yields, easy to execute, short reaction time, modular in nature, mild condition, readily available starting materials, etc. Moreover, the resulting regioselective triazoles can serve as amide bond isosteres, a privileged functional group in drug discovery and development. More than hundreds of reviews had been devoted to the 'Click Chemistry' in special reference to 1,4-disubstituted triazoles, while only little efforts were made for an opposite regioisomer i.e., 1,5-disubstituted triazole. Herein, we have presented various classical approaches for an expeditious synthesis of a wide range of biologically relevant 1,5- disubstituted 1,2,3-triazole analogues. The syntheses of such a class of diversly functionalized triazoles have emerged as a crucial investigation in the domain of chemistry and biology. This tutorial review covers the literature assessment on the development of various synthetic protocols for the functionalized 1,5-disubstituted triazoles reported during the last 12 years.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"1 1","pages":"513-558"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"68008492","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}

{"title":"A Bird's Eye Review of Recent Reports on 1,3,4-oxadiazoles' Anti-inflammatory Insights Perspectives.","authors":"Tarun Chaudhary, Prabhat Kumar Upadhyay","doi":"10.2174/1570179420666230508124847","DOIUrl":"10.2174/1570179420666230508124847","url":null,"abstract":"<p><p>Anti-inflammatory agents suppress inflammatory mediators such as prostaglandins, prostacyclins, cytokines, thromboxane, histamine, bradykinins, COX-I and COX-II, 5-LOX, and other substances. These inflammatory chemicals create inflammatory responses when tissue is injured by trauma, bacteria, heat, toxins, or other factors. These inflammatory reactions may result in fluid flow from the blood vessels into the tissues, resulting in swelling. When the therapeutic importance of these clinically beneficial medications in treating inflammation was recognized, it spurred the invention of even more powerful and important molecules. Oxadiazole derivatives are exceptionally potent NSAIDs, and they are widely used. Comprehensive biochemical, structure-activity-relationship and pharmacological investigations have demonstrated that these 1,3,4-oxadiazole compounds exhibit anti-inflammatory properties. This review article outlines the synthesis scheme for 1,3,4-oxadiazole used in treating inflammation.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"595-606"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9800924","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}

{"title":"Intramolecular Click Cycloaddition Reactions: Synthesis of 1,2,3-Triazoles.","authors":"Zahra Tashrifi, Mohammad Mohammadi Khanaposhtani, Saeed Bahadorikhalili, Bagher Larijani, Mohammad Mahdavi","doi":"10.2174/1570179420666230407103320","DOIUrl":"10.2174/1570179420666230407103320","url":null,"abstract":"<p><p>Click Chemistry, as a powerful tool, has been used for the synthesis of a variety of 1,2,3-triazoles. Among click cycloaddition reactions, intramolecular click reactions carried out in azido-alkyne precursors has not been thoroughly reviewed. Hence, in this review, we have summarized and categorised the recent literature (from 2012 on) based on the azidoalkynyl precursor's type and a brief and concise description of the involved mechanisms is presented. Accordingly, we have classified the relevant literature into three categories: (1) substitution precursors (2) addition and (3) multi-component reaction (MCR) products.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"166-194"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9251422","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}

{"title":"Triazole-linked Nucleic Acids: Synthesis, Therapeutics and Synthetic Biology Applications.","authors":"Vivek K Sharma, Priyanka Mangla, Sunil K Singh, Ashok K Prasad","doi":"10.2174/1570179420666230502123950","DOIUrl":"10.2174/1570179420666230502123950","url":null,"abstract":"<p><p>This article covers the triazole-linked nucleic acids where the triazole linkage (TL) replaces the natural phosphate backbone. The replacement is done at either a few selected linkages or all the phosphate linkages. Two triazole linkages, the four-atom TL1 and the six-atom TL2, have been discussed in detail. These triazole-modified oligonucleotides have found a wide range of applications, from therapeutics to synthetic biology. For example, the triazole-linked oligonucleotides have been used in the antisense oligonucleotide (ASO), small interfering RNA (siRNA) and clustered regularly interspaced short palindromic repeats (CRISPR)-Cas9 technology as therapeutic agents. Due to the ease of the synthesis and a wide range of biocompatibility, the triazole linkage TL2 has been used to assemble a functional 300-mer DNA from alkyne- and azide-functionalized 100-mer oligonucleotides as well as an epigenetically modified variant of a 335 base-pair gene from ten short oligonucleotides. These outcomes highlight the potential of triazole-linked nucleic acids and open the doors for other TL designs and artificial backbones to fully exploit the vast potential of artificial nucleic acids in therapeutics, synthetic biology and biotechnology.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"436-455"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9404578","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}

{"title":"Hybrids of Benzimidazole-oxadiazole: A New Avenue for Synthesis, Pharmacological Activity and Recent Patents for the Development of More Effective Ligands.","authors":"Gunjan Bhasker, Salahuddin, Avijit Mazumder, Rajnish Kumar, Greesh Kumar, Mohamed Jawed Ahsan, Mohammad Shahar Yar, Fahad Khan, Bhupinder Kapoor","doi":"10.2174/0115701794260740231010111408","DOIUrl":"10.2174/0115701794260740231010111408","url":null,"abstract":"<p><strong>Background: </strong>Two significant families of compounds i.e. 1,3,4-oxadiazole and benzimidazole, have undergone extensive investigation into their pharmacological characteristics and possible therapeutic applications. Both classes have shown their potential in a variety of applications, and because of their synergistic interactions, they may have an even better therapeutic impact when combined.</p><p><strong>Objectives: </strong>To produce a specific molecule with potent therapeutic properties, it is now common methods to combine at least two pharmacophores. This facilitates interaction with several targets, enhances biological functions, or eliminates adverse effects associated with them.</p><p><strong>Conclusion: </strong>The synthesis of benzimidazole-1,3,4-oxadiazole hybrid compounds has recently involved the use of several synthetic techniques, all of which are detailed in the literature along with the advantages and disadvantages. It has been noted that the structure-activity relationship relates their pharmacological actions to their molecular structure. In order to set the stage for future research, the study aims to provide researchers with an effective toolbox and an understanding of benzimidazole and 1,3,4-oxadiazole hybrid compounds.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"976-1013"},"PeriodicalIF":2.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"71421634","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}

{"title":"Synthesis of Novel Fluoro Phenyl Triazoles <i>Via</i> Click Chemistry with or without Microwave Irradiation and their Evaluation as Anti-proliferative Agents in SiHa Cells.","authors":"Johana Aguilar, Elisa Leyva, Silvia Elena Loredo-Carrillo, Agobardo Cárdenas-Chaparro, Antonio Martínez-Richa, Hiram Hernández-López, Jorge Gustavo Araujo-Huitrado, Angélica Judith Granados-López, Yamilé López-Hernández, Jesús Adrián López","doi":"10.2174/1570179420666230420084000","DOIUrl":"10.2174/1570179420666230420084000","url":null,"abstract":"<p><strong>Aims: </strong>Perform the synthesis of novel fluoro phenyl triazoles <i>via</i> click chemistry with or without microwave irradiation and their evaluation as anti-proliferative agents in SiHa cells.</p><p><strong>Background: </strong>Triazoles are heterocyclic compounds containing a five-member ring with two carbon and three nitrogen atoms. They are of great importance since many of them have shown to have biological activity as antifungal, antiviral, antibacterial, anti-HIV, anti-tuberculosis, vasodilator, and anticancer agents.</p><p><strong>Objectives: </strong>Synthesize novel fluoro phenyl triazoles <i>via</i> click chemistry and evaluate their antiproliferative activity.</p><p><strong>Methods: </strong>First, several fluorophenyl azides were prepared. Reacting these aryl azides with phenylacetylene in the presence of Cu(I) catalyst, the corresponding fluoro phenyl triazoles were obtained by two methodologies, stirring at room temperature and under microwave irradiation at 40ºC. In addition, their antiproliferative activity was evaluated in cervical cancer SiHa cells.</p><p><strong>Results: </strong>Fluoro phenyl triazoles were obtained within minutes by means of microwave irradiation. The compound 3f, containing two fluorine atoms next to the carbon connected to the triazole ring, was the most potent among the fluoro phenyl triazoles tested in this study. Interestingly, the addition of a fluorine atom to the phenyl triazole structure in a specific site increases its antiproliferative effect as compared to parent phenyl triazole 3a without a fluorine atom.</p><p><strong>Conclusion: </strong>Several fluoro phenyl triazoles were obtained by reacting fluoro phenyl azides with phenylacetylene in the presence of copper sulphate, sodium ascorbate and phenanthroline. Preparation of these triazoles with MW irradiation represents a better methodology since they are obtained within minutes and higher yields of cleaner compounds are obtained. In terms of biological studies, the proximity between fluorine atom and triazole ring increases its biological activity.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"559-570"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9385696","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}

{"title":"Synthesis of Phentermine and its Derivatives.","authors":"Khushbu Upadhyaya, Shruti Shukla, Bharti Parkash Meena, Jaya Dwivedi","doi":"10.2174/1570179420666230530095245","DOIUrl":"10.2174/1570179420666230530095245","url":null,"abstract":"<p><p>In recent years, a growing global concern has been obesity. Patients with obesity are at major risk for developing a number of diseases. These diseases may significantly impact patient's daily lives and increase the mortality rate. Over a year, medication for obesity has undergone substantial changes. An amphetamine-like prescription drug called Phentermine (Adipex-P, Lomaira) is used to suppress appetite. In the last few years, Phentermine and its derivatives have attracted much attention due to their use in weight reduction; by reducing appetite or prolonging the feeling of fullness, it can aid in weight reduction. So, reviewing the synthesis of Phentermine and its derivatives becomes imperative. Therefore, various synthetic routes for Phentermine (from benzaldehyde, isopropyl phenyl ketone, dimethyl benzyl carbinol) and its derivatives synthesis, involving ortho-palladation, are also reviewed here comprehensively.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"583-594"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9545741","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}

{"title":"An Overview of Julia-lythgoe Olefination.","authors":"Vijayan Varsha, Sankaran Radhika, Gopinathan Anilkumar","doi":"10.2174/1570179420666230510104114","DOIUrl":"10.2174/1570179420666230510104114","url":null,"abstract":"<p><p>Julia-Lythgoe olefination (or simply Julia olefination) is an olefination process between phenyl sulfones and aldehydes (or ketones) to give alkenes after alcohol functionalization and reductive elimination using sodium amalgam or SmI2. It is mainly used to synthesize E-alkenes and is a key step in numerous total syntheses of many natural products. This review exclusively deals with the Julia-Lythgoe olefination and concentrates mainly on the applications of this reaction in natural product synthesis covering literature up to 2021.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"97-126"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9859910","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}