Pub Date : 2024-03-12DOI: 10.2174/0113852728283109240216051223
Rinat R. Gubaidullin, Yulia A. Perfilova, Lyudmila V. Parfenova
: Camphor and carvone exhibit a broad spectrum of biological activity, which determines the prospect of their use as a platform for functionalization to obtain the analogues as potential drugs. The functionalization of camphor and carvone often involves changes to the skeleton of the molecules or their fragmentation. Therefore, in modern medicinal chemistry, research aimed at the development of effective approaches to the synthesis of semi-synthetic derivatives of camphor and carvone with preservation of the native framework, demonstrating high biological activity, is in demand. The present work is aimed at the synthesis of new propynyl analogues of camphor and carvone, as well as their conjugates with mono- and disaccharides via Cu-catalyzed cycloaddition of acetylenes and azides (CuAAC). Alkylation of camphor and carvone with propargyl bromide in the presence of the base KN(SiMe3)2–Et3B in 1,2-dimethoxyethane (DME) at room temperature provides the target products with yields of 69% and 47%, respectively. Glycosyl azides were obtained by the reaction of peracetylated sugars with trimethylsilyl azide in the presence of SnCl4.The synthesis of 1,2,3-triazolyl glycoconjugates of camphor and carvone with mono- and disaccharides was carried out through Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides to acetylenes (CuAAC) in the presence of Cu and CuSO4·5H2O. The structures of the synthesized compounds were determined by NMR. The new propynyl-substituted camphor and carvone, as well as their 1,2,3-triazolylglycoconjugates, can be used as promising building blocks for medicine chemistry.
:樟脑和香芹酮具有广泛的生物活性，这决定了它们有望被用作功能化平台，以获得类似物作为潜在药物。樟脑和香芹酮的功能化通常涉及改变分子的骨架或使其破碎。因此，在现代药物化学中，需要开发有效的方法来合成樟脑和香芹酮的半合成衍生物，同时保留其原生骨架，并显示出较高的生物活性。本研究旨在通过铜催化的乙炔和叠氮化物环加成（CuAAC）合成樟脑和香芹酮的新丙炔基类似物及其与单糖和二糖的共轭物。室温下，在 1,2 二甲基甲氧基乙烷（DME）中，在碱 KN(SiMe3)2-Et3B 的存在下，樟脑和香芹酮与溴化丙炔发生烷基化反应，生成的目标产物的产率分别为 69% 和 47%。在 Cu 和 CuSO4-5H2O 的存在下，通过 Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides to acetylenes (CuAAC)，合成了樟脑和香芹酮与单糖和二糖的 1,2,3-三唑基糖共轭物。通过核磁共振确定了合成化合物的结构。新的丙炔基取代的樟脑和香芹酮以及它们的 1,2,3-三唑基甘氨酰共轭物可作为药物化学的有前途的构建基块。
{"title":"Synthesis of Novel Propynyl Monoterpene Analogues and their Conjugates with β-DGlucopyranosides","authors":"Rinat R. Gubaidullin, Yulia A. Perfilova, Lyudmila V. Parfenova","doi":"10.2174/0113852728283109240216051223","DOIUrl":"https://doi.org/10.2174/0113852728283109240216051223","url":null,"abstract":": Camphor and carvone exhibit a broad spectrum of biological activity, which determines the prospect of their use as a platform for functionalization to obtain the analogues as potential drugs. The functionalization of camphor and carvone often involves changes to the skeleton of the molecules or their fragmentation. Therefore, in modern medicinal chemistry, research aimed at the development of effective approaches to the synthesis of semi-synthetic derivatives of camphor and carvone with preservation of the native framework, demonstrating high biological activity, is in demand. The present work is aimed at the synthesis of new propynyl analogues of camphor and carvone, as well as their conjugates with mono- and disaccharides via Cu-catalyzed cycloaddition of acetylenes and azides (CuAAC). Alkylation of camphor and carvone with propargyl bromide in the presence of the base KN(SiMe3)2–Et3B in 1,2-dimethoxyethane (DME) at room temperature provides the target products with yields of 69% and 47%, respectively. Glycosyl azides were obtained by the reaction of peracetylated sugars with trimethylsilyl azide in the presence of SnCl4.The synthesis of 1,2,3-triazolyl glycoconjugates of camphor and carvone with mono- and disaccharides was carried out through Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides to acetylenes (CuAAC) in the presence of Cu and CuSO4·5H2O. The structures of the synthesized compounds were determined by NMR. The new propynyl-substituted camphor and carvone, as well as their 1,2,3-triazolylglycoconjugates, can be used as promising building blocks for medicine chemistry.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"290 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140115340","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Heterocyclic compounds containing nitrogen and their derivatives have been a rich source of medicines. Pyrazole, a five-membered ring structure, offers a variety of functionalities as well as stereo-chemical complexity. Studies conducted over the past 10 years revealed that an increasing amount of research has been performed on different pyrazole derivatives and their physiological and pharmacological activities. The objective of these studies is to uncover the full potential of pyrazole derivatives by elucidating the many drug-like properties and their link between the structure and mode of action. Here, we discuss different ways of synthesizing pyrazole derivatives. Due to recent advances in synthetic medicinal chemistry, this class of compounds can be readily developed and becomes a viable target for the discovery of novel drugs.
{"title":"Synthetic Update on Antimicrobial Potential of Novel Pyrazole Derivatives: A Review","authors":"Sucheta Singh, Sumit Tahlan, Kuldeep singh, Prabhakar Kumar Verma","doi":"10.2174/0113852728292094240216045039","DOIUrl":"https://doi.org/10.2174/0113852728292094240216045039","url":null,"abstract":": Heterocyclic compounds containing nitrogen and their derivatives have been a rich source of medicines. Pyrazole, a five-membered ring structure, offers a variety of functionalities as well as stereo-chemical complexity. Studies conducted over the past 10 years revealed that an increasing amount of research has been performed on different pyrazole derivatives and their physiological and pharmacological activities. The objective of these studies is to uncover the full potential of pyrazole derivatives by elucidating the many drug-like properties and their link between the structure and mode of action. Here, we discuss different ways of synthesizing pyrazole derivatives. Due to recent advances in synthetic medicinal chemistry, this class of compounds can be readily developed and becomes a viable target for the discovery of novel drugs.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140115393","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-03-12DOI: 10.2174/0113852728295463240216074814
Hena Khatoon, Emilia Abdul Malek
: Cyclodextrins (CDs), which are a type of cyclic oligosaccharides, are widely used in supramolecular chemistry. For example, they can be used to encapsulate volatile compounds, such as drugs, within their hydrophobic cavity. This encapsulation reduces the volatility of the compounds and helps to retain their desired properties. Due to its extraordinary properties, cyclodextrins have been utilized as catalysts in numerous organic synthesis processes. An intrinsic objective of organic chemists is to optimize the efficacy of organic synthesis through the mitigation of chemical waste and energy expenditure. Utilizing water as a green solvent is, therefore, economical, environmentally sustainable, and secure. It appears that employing water in conjunction with a recyclable catalyst is the most effective method for supramolecular catalysis. As a consequence, we focused this review on the use of water as a solvent and cyclodextrin as a polymer catalyst to produce quinoxaline derivatives in an environmentally friendly and sustainable manner
{"title":"A Focussed Analysis of Β-cyclodextrins for Quinoxaline Derivatives Synthesis","authors":"Hena Khatoon, Emilia Abdul Malek","doi":"10.2174/0113852728295463240216074814","DOIUrl":"https://doi.org/10.2174/0113852728295463240216074814","url":null,"abstract":": Cyclodextrins (CDs), which are a type of cyclic oligosaccharides, are widely used in supramolecular chemistry. For example, they can be used to encapsulate volatile compounds, such as drugs, within their hydrophobic cavity. This encapsulation reduces the volatility of the compounds and helps to retain their desired properties. Due to its extraordinary properties, cyclodextrins have been utilized as catalysts in numerous organic synthesis processes. An intrinsic objective of organic chemists is to optimize the efficacy of organic synthesis through the mitigation of chemical waste and energy expenditure. Utilizing water as a green solvent is, therefore, economical, environmentally sustainable, and secure. It appears that employing water in conjunction with a recyclable catalyst is the most effective method for supramolecular catalysis. As a consequence, we focused this review on the use of water as a solvent and cyclodextrin as a polymer catalyst to produce quinoxaline derivatives in an environmentally friendly and sustainable manner","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"160 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140115187","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-03-06DOI: 10.2174/0113852728293307240208160333
Helene Pellissier
: The cheaper and less-toxic metals of Group 4 compared with common metals used in catalysis are increasingly applied in catalysis, resulting in the development of many novel greener transformations. Zirconium is abundant, non-toxic, and exhibits a remarkably diversified chemical reactivity among these metals. Since the first asymmetric zirconium-catalyzed reaction disclosed by Nugent in 1992, a wide variety of chiral zirconium catalysts have been proven to be capable of promoting many types of highly enantioselective transformations, spanning from standard reactions, such as Friedel‒Crafts reactions, cycloadditions, aldol reactions, Mannich reactions, epoxidations, nucleophilic additions to carbonyl compounds and derivatives, cyanations, ring-opening reactions, hydroxylations, hydroformylations, carboaluminations among others, to more modern and complex domino and tandem processes. This review aims to collect the major progress achieved in the field of enantioselective transformations of all types promoted by chiral zirconium catalysts, covering the literature since the beginning of 2003 and illustrating the power of these non-toxic catalysts to provide high enantioselectivity in almost all kinds of asymmetric organic reactions. It is divided into ten parts, focussing consecutively on enantioselective Friedel‒Crafts reactions, cycloadditions, aldol reactions, Mannich reactions, epoxidations, additions of alkylzinc reagents to imines, cyanations, ring-opening reactions, hydroxylations, and domino/ tandem reactions. The diversity of these transformations well reflects that of the products synthesized. For example, chiral indole and pyrrole derivatives were prepared from Friedel‒Crafts reactions; pyranones, pyridones and pyrazolidines from cycloadditions; β-hydroxy α-diazo carbonyl compounds, βhydroxy (thio)esters and β-hydroxy-α-amino acid derivatives from aldol reactions; β-amino (thio)esters from Mannich reactions; functionalized epoxides from epoxidations; amines from additions of alkylzinc reagents to imines; amino nitriles from cyanations; 1,2-diamines and β-vinyloxy alcohols from ring-opening processes; 2- hydroxy 1-indanones from hydroxylations; various amines, 1,3-anti-diol monoesters, β-amino esters, α,βdihydroxy acid derivatives, α-amino ketones, indoles, cyclopentane and aryl α-aminophosphonates from domino/ tandem reactions. Furthermore, the utility of these novel methodologies was demonstrated in the total synthesis of numerous essential bioactive products, such as (+)-prelactone C, (+)-9-deoxygoniopypyrone, (+)- coniine, vancomycin, (+)-fusarisetin A, mycolipenic acid, onchidin, indoxacarb, tachykinin receptor antagonists, cerebroprotecting agent MS-153, and L-erythro-sphingosine. The advances achieved in the last three decades demonstrate that the non-toxicity, abundance, and efficiency of zirconium make its application in catalysis suiting the growing demand for more environmentally benign processes, offering the real opportunity t
{"title":"Enantioselective Zirconium-catalyzed Transformations","authors":"Helene Pellissier","doi":"10.2174/0113852728293307240208160333","DOIUrl":"https://doi.org/10.2174/0113852728293307240208160333","url":null,"abstract":": The cheaper and less-toxic metals of Group 4 compared with common metals used in catalysis are increasingly applied in catalysis, resulting in the development of many novel greener transformations. Zirconium is abundant, non-toxic, and exhibits a remarkably diversified chemical reactivity among these metals. Since the first asymmetric zirconium-catalyzed reaction disclosed by Nugent in 1992, a wide variety of chiral zirconium catalysts have been proven to be capable of promoting many types of highly enantioselective transformations, spanning from standard reactions, such as Friedel‒Crafts reactions, cycloadditions, aldol reactions, Mannich reactions, epoxidations, nucleophilic additions to carbonyl compounds and derivatives, cyanations, ring-opening reactions, hydroxylations, hydroformylations, carboaluminations among others, to more modern and complex domino and tandem processes. This review aims to collect the major progress achieved in the field of enantioselective transformations of all types promoted by chiral zirconium catalysts, covering the literature since the beginning of 2003 and illustrating the power of these non-toxic catalysts to provide high enantioselectivity in almost all kinds of asymmetric organic reactions. It is divided into ten parts, focussing consecutively on enantioselective Friedel‒Crafts reactions, cycloadditions, aldol reactions, Mannich reactions, epoxidations, additions of alkylzinc reagents to imines, cyanations, ring-opening reactions, hydroxylations, and domino/ tandem reactions. The diversity of these transformations well reflects that of the products synthesized. For example, chiral indole and pyrrole derivatives were prepared from Friedel‒Crafts reactions; pyranones, pyridones and pyrazolidines from cycloadditions; β-hydroxy α-diazo carbonyl compounds, βhydroxy (thio)esters and β-hydroxy-α-amino acid derivatives from aldol reactions; β-amino (thio)esters from Mannich reactions; functionalized epoxides from epoxidations; amines from additions of alkylzinc reagents to imines; amino nitriles from cyanations; 1,2-diamines and β-vinyloxy alcohols from ring-opening processes; 2- hydroxy 1-indanones from hydroxylations; various amines, 1,3-anti-diol monoesters, β-amino esters, α,βdihydroxy acid derivatives, α-amino ketones, indoles, cyclopentane and aryl α-aminophosphonates from domino/ tandem reactions. Furthermore, the utility of these novel methodologies was demonstrated in the total synthesis of numerous essential bioactive products, such as (+)-prelactone C, (+)-9-deoxygoniopypyrone, (+)- coniine, vancomycin, (+)-fusarisetin A, mycolipenic acid, onchidin, indoxacarb, tachykinin receptor antagonists, cerebroprotecting agent MS-153, and L-erythro-sphingosine. The advances achieved in the last three decades demonstrate that the non-toxicity, abundance, and efficiency of zirconium make its application in catalysis suiting the growing demand for more environmentally benign processes, offering the real opportunity t","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140053868","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Naturally and synthetically obtained lipophilic α-amino acids exhibit diverse properties and applications in academia and industry. Unnatural hydrophobic/lipophilic amino acids lacking polarity in their side chains manifest the biologically significant structure of peptides and proteins. The hydrophobic effect of lipophilic amino acids stabilizes the structure of proteins, peptides, and enzymes during their indigenous folding-unfolding phenomena. The presence of these amino acids in the backbone of protein and peptide-derived drug delivery systems such as lysine-derived surfactants and glycodendrimers can also enhance the cell penetration of drugs of interest. Cationic poly-l-lysine dendrimers, α-amino oleic acid, and a naturally occurring cyclic heptadepsipeptide HUN7293 are recognized as promising biomaterials for developing prodrugs and also serve as biocompatible surfactants in the food and pharmaceutical industries. The synthesis of unnatural lipophilic amino acids, N-lauroyl sarcosine, N-lauroyl glutamic acid, N-octylglycine, N-myristoyl glycine etc. has gained attention for preparing novel compounds for advanced academic, industrial, and societal applications. This review article discusses the applications and synthesis of hydrophobic/lipophilic α-amino acids using ester enolate Claisen rearrangement, chiral auxiliary, chiral pool, chiral catalysts, and many more relevant methodologies.
{"title":"Overview of Synthesis and Applications of Unnatural Lipophilic α-Amino Acids","authors":"Prateek Bhamboo, Smritilekha Bera, Dhananjoy Mondal","doi":"10.2174/0113852728297799240206084937","DOIUrl":"https://doi.org/10.2174/0113852728297799240206084937","url":null,"abstract":": Naturally and synthetically obtained lipophilic α-amino acids exhibit diverse properties and applications in academia and industry. Unnatural hydrophobic/lipophilic amino acids lacking polarity in their side chains manifest the biologically significant structure of peptides and proteins. The hydrophobic effect of lipophilic amino acids stabilizes the structure of proteins, peptides, and enzymes during their indigenous folding-unfolding phenomena. The presence of these amino acids in the backbone of protein and peptide-derived drug delivery systems such as lysine-derived surfactants and glycodendrimers can also enhance the cell penetration of drugs of interest. Cationic poly-l-lysine dendrimers, α-amino oleic acid, and a naturally occurring cyclic heptadepsipeptide HUN7293 are recognized as promising biomaterials for developing prodrugs and also serve as biocompatible surfactants in the food and pharmaceutical industries. The synthesis of unnatural lipophilic amino acids, N-lauroyl sarcosine, N-lauroyl glutamic acid, N-octylglycine, N-myristoyl glycine etc. has gained attention for preparing novel compounds for advanced academic, industrial, and societal applications. This review article discusses the applications and synthesis of hydrophobic/lipophilic α-amino acids using ester enolate Claisen rearrangement, chiral auxiliary, chiral pool, chiral catalysts, and many more relevant methodologies.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140053637","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-03-01DOI: 10.2174/0113852728284871240215103216
Zeynep Özsırkıntı, Abdul Hakim Hakimi, Mehmet Erşatır, Murat Türk, Onur Demirkol, Elife Sultan Giray
aims: Using supercrticial diethylether as a reaction solvent Abstract: Due to very good biological activity and use as fluorescent probes, coumarin synthesis and developing new synthesis methods are still an attractive area for many research groups. In this work, for the first time, a novel, mild, and green method has been developed for coumarin synthesis by using supercritical diethyl ether as a reaction medium. The optimum conditions for the synthesis of 3-acetylcoumarins and 4-methylcoumarins have been explored. These newly established techniques could be a favourable approach against two traditional synthetic routes in terms of green chemistry criteria for the synthesis of important intermediates, 3-acetyl coumarins and 4-methyl coumarins. 4-Methyl coumarins have been obtained in good-to-excellent yields (63-87%); for example, b-methylumbelliferone, a naturally bioactive coumarin compound, was synthesised in 30 min at 200°C, resulting in 87% yield, while several 3-acetyl coumarins were synthesized in very good yields (28-96%).
{"title":"Using Supercritical Diethyl Ether as the Reaction Medium for the Synthesis of 3-Acetyl and 4-Methyl Substituted Coumarins","authors":"Zeynep Özsırkıntı, Abdul Hakim Hakimi, Mehmet Erşatır, Murat Türk, Onur Demirkol, Elife Sultan Giray","doi":"10.2174/0113852728284871240215103216","DOIUrl":"https://doi.org/10.2174/0113852728284871240215103216","url":null,"abstract":"aims: Using supercrticial diethylether as a reaction solvent Abstract: Due to very good biological activity and use as fluorescent probes, coumarin synthesis and developing new synthesis methods are still an attractive area for many research groups. In this work, for the first time, a novel, mild, and green method has been developed for coumarin synthesis by using supercritical diethyl ether as a reaction medium. The optimum conditions for the synthesis of 3-acetylcoumarins and 4-methylcoumarins have been explored. These newly established techniques could be a favourable approach against two traditional synthetic routes in terms of green chemistry criteria for the synthesis of important intermediates, 3-acetyl coumarins and 4-methyl coumarins. 4-Methyl coumarins have been obtained in good-to-excellent yields (63-87%); for example, b-methylumbelliferone, a naturally bioactive coumarin compound, was synthesised in 30 min at 200°C, resulting in 87% yield, while several 3-acetyl coumarins were synthesized in very good yields (28-96%).","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140018130","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-02-27DOI: 10.2174/0113852728288581240125112724
Angie D. Arboleda, Leydi M. Moreno, Rodrigo Abonia
: The pyranoquinoline frameworks have a wide distribution in natural products and have displayed a great amplitude of biological activities, attracting the attention of synthetic and medicinal chemists due to their usefulness in agrochemical and pharmaceutical industries. Among the twenty possible isomeric pyranoquinoline frameworks, research reports for only six of them that were found during the period of time covered in this review article (i.e. 2000 to 2023). According to the literature reports during this frame of time, the synthesis of pyranoquinoline derivatives was achieved by following three general synthetic approaches [i.e. (i) via multicomponent cyclizations (MCC), (ii) via bimolecular cyclizations (BMC) and via intramolecular cyclizations (IMC)], mediated by catalyst-free conditions or by diverse environmentally friendly catalysts, in which mechanistic proposal was discussed for several of such processes. Additionally, various obtained pyranoquinoline derivatives reported in this review were subjected to diverse biological evaluations, such as Parkinson´s and Alzheimer´s diseases, as antibacterials, antifungals, and anticancer drugs, among others, indicating the promising biological potential of this class of heterocyclic structure.
{"title":"Synthetic Approaches for Pyranoquinolines: A Concise Review","authors":"Angie D. Arboleda, Leydi M. Moreno, Rodrigo Abonia","doi":"10.2174/0113852728288581240125112724","DOIUrl":"https://doi.org/10.2174/0113852728288581240125112724","url":null,"abstract":": The pyranoquinoline frameworks have a wide distribution in natural products and have displayed a great amplitude of biological activities, attracting the attention of synthetic and medicinal chemists due to their usefulness in agrochemical and pharmaceutical industries. Among the twenty possible isomeric pyranoquinoline frameworks, research reports for only six of them that were found during the period of time covered in this review article (i.e. 2000 to 2023). According to the literature reports during this frame of time, the synthesis of pyranoquinoline derivatives was achieved by following three general synthetic approaches [i.e. (i) via multicomponent cyclizations (MCC), (ii) via bimolecular cyclizations (BMC) and via intramolecular cyclizations (IMC)], mediated by catalyst-free conditions or by diverse environmentally friendly catalysts, in which mechanistic proposal was discussed for several of such processes. Additionally, various obtained pyranoquinoline derivatives reported in this review were subjected to diverse biological evaluations, such as Parkinson´s and Alzheimer´s diseases, as antibacterials, antifungals, and anticancer drugs, among others, indicating the promising biological potential of this class of heterocyclic structure.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"76 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140005304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-02-27DOI: 10.2174/0113852728284846240124052127
Dhananjay N. Gaikwad, Suresh T. Gaikwad, Rajesh K. Manjul, Anjali S. Rajbhoj, Dayanand M. Suryavanshi
: This article highlights current developments in iron-doped nanocatalyst-based solvent-free organic reactions. These catalysts have the potential to speed up processes under safe environmental settings and eliminate the need for hazardous organic solvents. Its application in a variety of fields is mostly due to its superparamagnetic nano diameters, which are affordable, easily separable, reusable, and eco-friendly. Thus, the present review article focuses on the compendious account of various doped iron nanocatalysts reported catalyzing organic transformation, including synthesis of bioactive compounds, condensation, multicomponent, annulation, esterification, coupling, alkylation, acylation reactions. The development of innovative, highly active, and reusable magnetic iron nanocomposite catalysts is crucial for the future of catalysis as it will pave the way for the creation of environmentally friendly and sustainable technology. The review will provide valuable insights for researchers who are designing new functionalized doped iron catalysts or utilizing these catalysts for various organic transformations that promote sustainable development. The development of new precursors and synthesis techniques, as well as recent improvements in the synthesis of these catalysts, are described. The article also emphasizes the significance of comprehending the underlying processes of these catalytic events, as well as the difficulties and possibilities for further study in this field. The potential of iron-doped nanocatalysts as an environmentally friendly and long-lasting method of organic synthesis is emphasized throughout this review.
{"title":"Recent Advances in Solvent-free Organic Transformation Via Iron-doped Nanocatalyst","authors":"Dhananjay N. Gaikwad, Suresh T. Gaikwad, Rajesh K. Manjul, Anjali S. Rajbhoj, Dayanand M. Suryavanshi","doi":"10.2174/0113852728284846240124052127","DOIUrl":"https://doi.org/10.2174/0113852728284846240124052127","url":null,"abstract":": This article highlights current developments in iron-doped nanocatalyst-based solvent-free organic reactions. These catalysts have the potential to speed up processes under safe environmental settings and eliminate the need for hazardous organic solvents. Its application in a variety of fields is mostly due to its superparamagnetic nano diameters, which are affordable, easily separable, reusable, and eco-friendly. Thus, the present review article focuses on the compendious account of various doped iron nanocatalysts reported catalyzing organic transformation, including synthesis of bioactive compounds, condensation, multicomponent, annulation, esterification, coupling, alkylation, acylation reactions. The development of innovative, highly active, and reusable magnetic iron nanocomposite catalysts is crucial for the future of catalysis as it will pave the way for the creation of environmentally friendly and sustainable technology. The review will provide valuable insights for researchers who are designing new functionalized doped iron catalysts or utilizing these catalysts for various organic transformations that promote sustainable development. The development of new precursors and synthesis techniques, as well as recent improvements in the synthesis of these catalysts, are described. The article also emphasizes the significance of comprehending the underlying processes of these catalytic events, as well as the difficulties and possibilities for further study in this field. The potential of iron-doped nanocatalysts as an environmentally friendly and long-lasting method of organic synthesis is emphasized throughout this review.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140005296","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: An efficient transition metal catalyst-free protocol for the synthesis of unsymmetrical diaryl tellurides has been developed by the reaction of diaryl tellurides and aryl diazonium tetrafluoroborates under mechanical ball milling in the absence of any solvent and base under room temperature. InBr (Indium Bromide) plays an important role in generating the organotelluride nucleophile via the Te-Te bond cleavage of ditelluride. A library of diaryl tellurides bearing both electron-donating and withdrawing groups in the aromatic ring has been synthesized in good to excellent yields by this protocol. Despite very high synthetic importance of diaryl tellurides in the field of organic synthesis, very few protocols have been reported to date for their synthesis. The reactions were also performed on a gram scale without any considerable change in the yields, which surely broadened the applicability of this methodology in the industrial field.
{"title":"Synthesis of Unsymmetrical Diaryl Tellurides Under Mechanical Ball Milling in Room Temperature","authors":"Anup Roy, Subir Panja, Pradipta Kumar Basu, Debasish Kundu","doi":"10.2174/0113852728291474240123065931","DOIUrl":"https://doi.org/10.2174/0113852728291474240123065931","url":null,"abstract":": An efficient transition metal catalyst-free protocol for the synthesis of unsymmetrical diaryl tellurides has been developed by the reaction of diaryl tellurides and aryl diazonium tetrafluoroborates under mechanical ball milling in the absence of any solvent and base under room temperature. InBr (Indium Bromide) plays an important role in generating the organotelluride nucleophile via the Te-Te bond cleavage of ditelluride. A library of diaryl tellurides bearing both electron-donating and withdrawing groups in the aromatic ring has been synthesized in good to excellent yields by this protocol. Despite very high synthetic importance of diaryl tellurides in the field of organic synthesis, very few protocols have been reported to date for their synthesis. The reactions were also performed on a gram scale without any considerable change in the yields, which surely broadened the applicability of this methodology in the industrial field.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140005302","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
: Genus berberis, an evergreen shrub of about 500 plant species found in subtropical and temperate regions but only some of them are investigated and evaluated for their phytochemistry and bioactivity. These plants are spread worldwide and help in the nourishment of humans and animals. Almost all parts of the plant are investigated for pharmacological and phytochemical purposes, including, roots, fruits, stems, buds, seeds, branches, flowers, leaves, and whole plant. Rasaut, an extract of either the stem or root of Berberis aristata is mentioned in the ancient Ayurvedic literature of India for treating indolent ulcers and eye disorders, and B. vulgaris is still used to treat malaria in North America. They have many medicinal properties and compounds that are bioactive like berberine. Berberine possesses anticancer, antimicrobial, and other activities. The plants contain a number of alkaloids, tannins, flavonoids, carotenoids, terpenoids, and other categories of chemical constituents. The alkaloidal compounds are isolated and evaluated for various activities and are found to be active. The researchers are continuously working to get novel exploration regarding the Genus Berberis . Here in the review, traditional and folkloric uses of the genus were also described. Apart from this, they possess numerous activities like anticancer, antimicrobial, antioxidant, anti-inflammatory, antidiabetic, antiulcer, antiviral and, wound healing and many more. These activities were authenticated by in-vitro and in-vivo methods. The aim of this review is to update and systematically arrange information in one platform. In this review, we extracted the current information from Pubmed, Googlescolar, Scifinder and many more databases.
{"title":"A Review on Folklore Uses, Phytoconstituents and Pharmacological Activities of the Genus Berberis","authors":"Zulfa Nooreen, Awani Kumar Rai, Poonam Jaisal, Fariha Summayya, Ankita Wal, Nasir A Siddique","doi":"10.2174/0113852728277490231211045732","DOIUrl":"https://doi.org/10.2174/0113852728277490231211045732","url":null,"abstract":": Genus berberis, an evergreen shrub of about 500 plant species found in subtropical and temperate regions but only some of them are investigated and evaluated for their phytochemistry and bioactivity. These plants are spread worldwide and help in the nourishment of humans and animals. Almost all parts of the plant are investigated for pharmacological and phytochemical purposes, including, roots, fruits, stems, buds, seeds, branches, flowers, leaves, and whole plant. Rasaut, an extract of either the stem or root of Berberis aristata is mentioned in the ancient Ayurvedic literature of India for treating indolent ulcers and eye disorders, and B. vulgaris is still used to treat malaria in North America. They have many medicinal properties and compounds that are bioactive like berberine. Berberine possesses anticancer, antimicrobial, and other activities. The plants contain a number of alkaloids, tannins, flavonoids, carotenoids, terpenoids, and other categories of chemical constituents. The alkaloidal compounds are isolated and evaluated for various activities and are found to be active. The researchers are continuously working to get novel exploration regarding the Genus Berberis . Here in the review, traditional and folkloric uses of the genus were also described. Apart from this, they possess numerous activities like anticancer, antimicrobial, antioxidant, anti-inflammatory, antidiabetic, antiulcer, antiviral and, wound healing and many more. These activities were authenticated by in-vitro and in-vivo methods. The aim of this review is to update and systematically arrange information in one platform. In this review, we extracted the current information from Pubmed, Googlescolar, Scifinder and many more databases.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2024-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139950918","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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