Current organic synthesis最新文献

{"title":"Synthesis and Antitumor Activity of Some New N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones","authors":"Hind M. A. Yahya, Jalal A. Zahra, Salim S. Sabri, Mustafa M. El-Abadelah, Sanaa Bardaweel","doi":"10.2174/0115701794282903231228055914","DOIUrl":"https://doi.org/10.2174/0115701794282903231228055914","url":null,"abstract":"Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. background: The hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, underwent reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized via interaction of the hy-drazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carbox-ylate, with the appropriate sec-cyclic amine. These new compounds were characterized by 1H-NMR, 13C-NMR, and HRMS spectral data and screened for their anticancer activities. Aims: This study aimed at the synthesis of novel N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate derivatives and investigated their potential as anticancer agents. Objective: The reaction of hydrazonoyl chloride with the appropriate sec-cyclic amine was applied to synthesize a novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5- yl)amidrazone carboxylates that incorporate N piperazines. Methods: A direct reaction of piperazines and related sec-cyclic amines with N-(4-oxoquinolin-5-yl)nitrile imine (1,3-dipole) was carried out for 8-10 h. conclusion: A novel set N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones were successfully synthesized. Several of these compounds showed moderate activity against three breast cancer cell lines (MCF-7, T47D, and MDA-MB-231) with IC50 values in the range =18-78µM compared to Doxorubicin Results: The 1,3-dipole, generated in situ from its hydrazonoyl chloride precursor in the presence of trimethylamine, is suitable for the facile synthesis of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates. Conclusion: This study led to the successful synthesis of novel N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones. All the examined compounds showed moderate activity with reasonable IC50 values in the micromolar range compared to Doxorubicin.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"42 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139498437","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 Brief Review on Recent Developments in Diels-Alder Reactions.","authors":"Manish Chaudhary, Shareef Shaik, Muskan Magan, Sharwan Hudda, Mukta Gupta, Gurvinder Singh, Pankaj Wadhwa","doi":"10.2174/0115701794262102231214074336","DOIUrl":"https://doi.org/10.2174/0115701794262102231214074336","url":null,"abstract":"<p><p>The [4+2] Diels-Alder cycloaddition has been widely used for the synthesis of six-mem-ber scaffolds. In recent years, there have been significant developments in this area, including the discovery and design of novel dienes and dienophiles with improved reactivity and selectivity. These new building blocks can be used to develop diverse molecular structures with functional group compatibility. Additionally, there is the use of catalytic systems and metal-mediated reactions to enable asymmetric [4+2] cycloadditions, resulting in enantiomerically enriched products. Over-all, recent studies related to [4+2] Diels-Alder cycloaddition using numerous dienes, dienophiles, and catalysts in different reaction conditions have significantly improved the efficiency, selectivity, and versatility of the reaction, making it an increasingly important tool in the synthesis of complex organic molecules as presented in this review. These advancements offer exciting possibilities for the development of new methods and reagents for the construction of six-membered rings and the synthesis of bioactive compounds.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139680878","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":"Organocatalytic Synthesis of (Hetero)arylidene Malononitriles Using a More Sustainable, Greener, and Scalable Strategy","authors":"Suzaimi Johari, Mohd Rafie Johan, Nader Ghaffari Khaligh","doi":"10.2174/0115701794268766231108110816","DOIUrl":"https://doi.org/10.2174/0115701794268766231108110816","url":null,"abstract":"Aim and Objective: The establishment of a green and sustainable Knoevenagel con-densation reaction in organic chemistry is still crucial. This work aimed to provide a newly de-veloped metal-free and halogen-free catalytic methodology for the synthesis of CS and (het-ero-)arylidene malononitriles in the laboratory and industrial scale. The Knoevenagel condensa-tion reaction of various carbonyl groups with malononitrile was investigated in ethanol, an eco-friendly medium, in the presence of seven nitrogen-based organocatalysts. Materials and Methods: A comparative study was conducted using two as-obtained and four commercially available nitrogen-based organocatalysts in Knoevenagel condensation reactions. The synthesis of CS gas (2-chlorobenzylidene malononitrile) using a closed catalytic system was optimized based on their efficiency and greener approach. Results: The conversion of 100% and excellent yields were obtained in a short time. The products could be crystallized directly from the reaction mixture. After separating pure products, the resi-due solution was employed directly in the next run without any concentration, activation, purification, or separation. Furthermore, the synthesis of 2-chlorobenzylidenemahmonitrile (CS) was carried out on a large scale using imidazole as a selected nitrogen-based catalyst, afforded crys-talline products with 95±2% yield in five consecutive runs. Conclusion: Energy efficiency, cost saving, greener conditions, using only 5 mol% of organo-catalyst, high recyclability of catalyst, prevention of waste, recycling extractant by a rotary evaporator for non-crystallized products, demonstrated the potential commercial production of CS using imidazole in ethanol as an efficient and highly recyclable catalytic system","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"65 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139465143","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":"Regioselective Synthesis of Cycloalkane-fused pyrazolo[4,3-e]pyridines through Tandem Reaction of 5-aminopyrazoles, Cyclic Ketones and Electron-rich Olefins","authors":"Paola Cuervo-Prado, Fabián Orozco-López, Christian Becerra-Rivas, Diego Leon-Vargas, John Lozano-Oviedo, Justo Cobo","doi":"10.2174/0115701794269765231204064930","DOIUrl":"https://doi.org/10.2174/0115701794269765231204064930","url":null,"abstract":"Background: Pyrazolopyridines are interesting fused heterocyclic pharmacophores that combine pyrazole and pyridine; two privileged nuclei extensively studied and with a wide range of applications. They can be obtained by a broad variety of synthetic methods among which multicomponent reactions have gained importance, especially from 5-aminopyrazoles and dielectrophilic reagents. However, the search for new approaches more in tune with sustainable chemistry and the use of unconventional heating in three-component synthesis are open and highly relevant study fields. Methods: A novel, practical and efficient three-component synthesis of cycloalkane-fused pyra-zolo[4,3-e]pyridines was developed through a tandem reaction of 5-aminopyrazoles, cyclic ke-tones and electron-rich olefins, using microwave induction in perfluorinated solvent and iodine as catalyst. objective: To apply the principles of sustainable chemistry through a microwave-induced synthesis in perfluorinated solvent to obtain novel cycloalkane-fused pyrazolo[4,3-e]pyridines, taking advantage of the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations. Results: The microwave-induced three-component approach applied in this work promoted the construction of 10 new pyrazolopyridines with high speed and excellent control of regioselec-tivity, favoring the linear product with good yields; where the versatility of electron-rich olefins in iodine-catalyzed cascade heterocyclizations, granted the additional benefit of easy isolation and the possibility to reuse the fluorous phase. Conclusions: Although pyrazolopyridines have been synthetically explored because of their structural and biological properties, most of the reported synthetic methods use common or even toxic organic solvents and conventional heating or multi-step processes. In contrast, this study applied a multicomponent methodology in a single step by microwave induction and with the versatility provided in this case by the use of perfluorinated solvent, which allowed easy isolation of the final product and recovery of the fluorous phase.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"94 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139465209","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":"Reactions and Biological Activities of Hydrazonoyl Halides","authors":"Munirah Alarbash, Yasir Al-Faiyz, Jeffery Wiggins, Abdelwahed Sayed","doi":"10.2174/0115701794268313231127110713","DOIUrl":"https://doi.org/10.2174/0115701794268313231127110713","url":null,"abstract":": This review covers the literature information on the chemistry of hydrazonoyl halides with different substrates to give heterocyclic compounds. From the foregoing survey, it seems this provides a useful and convenient strategy for the synthesis of numerous heterocyclic derivatives. The subject of such reactions is still ongoing and undoubtedly will provide new fused functionalized compounds of both industrial and biological interest. A literature survey revealed that a great deal of interest has been focused on the synthesis of functionalized heterocyclic compounds due to their wide range of biological activities, such as contact dermatitis, anthelmintic, antiviral, antimicrobial, herbicidal, and anti-cancer. On the other hand, hydrazonoyl halides are interesting synthons for valuable bioactive heterocyclic compounds. The reaction of hydrazonoyl halides with various types of substrates gave a huge number of different heterocyclic systems. In this review, we collected all reactions of hydrazonoyl halides with different moieties and classified them as aryl diazo of monoheterocycles, aryldiazo of 5,5-bis-heterocycles, aryldiazo of 5,6-bis-heterocycles, aryldiazo of 6,6-bis-heterocycles, aryldiazo of 5,5,6-tri-heterocycles, aryldiazo of 5,6,6-tri-heterocycles, aryldiazo of 6,6,6-tri-heterocycles, hetero annulation of bisheterocycles, hetero annulation of tri-heterocycles, hetero-annulation of tetra-heterocycles, synthesis of spiro-heterocycles, heterocyclic ring transformations, and 1,3-dipolar cycloaddition reactions catalyzed by transition metals using hydrazonoyl halides as substrates. Most reaction types have been successfully applied and used in the production of biologically active compounds. The aim of the present survey is to consider in the reader the opportunity interactions and biological activities of hydrazonoyl halides. The information of several artificial paths and varied physics-chemical factors of such heterocycles made a special consideration of chemists in different fields to yield a combinatorial library and carry out thorough efforts in the search for hydrazonoyl halides","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"59 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139465195","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 in free radical transformations of allenamides","authors":"Yongchun Liu, Zimin Wang, Rui Li, Yinhai Yao, Zhichuan Shi, Qin Sun, Guowei Deng","doi":"10.2174/0115701794269961231027054854","DOIUrl":"https://doi.org/10.2174/0115701794269961231027054854","url":null,"abstract":": Allenamides are special allenes, and the unique reactivity, selectivity (both stereoselective and regionally selective) and stability of allenamides have been widely studied. In this review, the development of the free radical transformation of allenamides over the last few years will be summarized. This review discusses in detail in three parts: intermolecular radical addition to C- X (X = N, S, O, Se) bonds, metal salt mediated cyclization of allenamides, and photocatalytic cyclization of allenamides. In addition, reasonable details of the mechanisms are provided for the vast majority of these transformations.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"51 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139103412","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":"Heteroaromatization of Coumarin Part I: Design, Synthesis, Reactions, Antitumor Activities of Novel Pyridine and Naphthyridine Derivatives","authors":"Rita Mohammed Ahmed Borik, Ashraf Hassan Fekry Abd El-Wahab","doi":"10.2174/0115701794265924230920061222","DOIUrl":"https://doi.org/10.2174/0115701794265924230920061222","url":null,"abstract":": A novel series of chromen-3-yl-pyridine moieties were synthesized. IR, NMR, and MS spectroscopy were used to confirm the structure of these novel compounds and study antitumor activity of these compounds. The structure-activity relationship investigation demonstrated that 2,4-diamino-5-(3- methoxyphenyl)-7-(2-oxo-2H-chromen-3-yl)-1,8-naphthyridine-3-carbonitrile (16), naphthyridine-3- carbonitrile derivatives 17, 18 and pyrido[2,3-d]pyrimidine derivative 12 were found to be more effective, while compounds 5a,b, 9c, 11, 13 and 14 showed moderate activity for antitumor activities. Objectives: The objective was to design a series of new chromen-3-yl-pyridine and pyrido[2,3-d]pyrimidine derivatives and study the antitumor of these compounds. Materials and Methods: The condensation reaction of 3-acetyl-2H-chromen-2-one with 3-methoxy benzaldehyde and malononitrile or ethyl cyanoacetate in the presence of ammonium acetate and acetic acid under reflux to give the corresponding chromen-3-yl pyridine-3-carbonitrile derivatives. Results: In this study, the antitumor activity of the synthesized compounds chromen-3-yl-pyridine derivatives has been determined for the broad spectrum of cytotoxic activity toward the investigated three cell lines and 5-Fluorouracil, as reference drugs. Conclusion: A series of new chromen-3-yl-pyridine and pyrido[2,3-d]pyrimidine derivatives were synthesized in this work. All compounds were evaluated for cytotoxic activity.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"39 1","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139084097","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":"Sustainable Green Synthesis of Pyrimidine Derivatives: Review on Multicomponent Synthesis, Catalysts and Techniques.","authors":"Elshimaa Mohmed Eid","doi":"10.2174/1570179420666230330081211","DOIUrl":"10.2174/1570179420666230330081211","url":null,"abstract":"<p><p>\"The founder of green chemistry explains how chemicals manufacturing must change to support a sustainable future.\" In this review, Green chemistry is considered in the synthesis of heterocycles compounds containing Pyrimidine nuclei using different catalyzes, solvents, and techniques for the synthesis of pyrimidine derivatives that achieve sustainability. The mentioned fused heterocycles are classified according to the type of ring system. The yield of the target molecules reported in the review is given in the reaction's last step.</p>","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":" ","pages":"127-139"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9227434","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":"Thematic Issue: Emerging Aspects of Click Chemistry.","authors":"Vinod K Tiwari, Diganta Sarma","doi":"10.2174/157017942104240218204834","DOIUrl":"https://doi.org/10.2174/157017942104240218204834","url":null,"abstract":"","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":"21 4","pages":"357-358"},"PeriodicalIF":1.8,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141158224","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":"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}