Pub Date : 2024-05-13DOI: 10.2174/0113852728304647240426201554
Sajad Safarzadeh, M. R. Mozafari, S. M. Naghib
The usage of nanoparticles in tissue engineering applications has increased significantly in the last several years. Functional tissues are developed by regulating cell proliferation, differentiation, and migration on nanostructured scaffolds containing cells. These scaffolds provide an environment that is more structurally supportive than the microarchitecture of natural bone. Given its exceptional properties, such as its osteogenic potential, biocompatibility, and biodegradability, chitosan is a good and promising biomaterial. Unfortunately, chitosan's low mechanical strength makes it unsuitable for load-bearing applications. By mixing chitosan with other biomaterials, this drawback might be mitigated. Bone tissue engineering uses both bioresorbable materials like tricalcium phosphate and bioactive materials like hydroxyapatite and bioglass. Alumina and titanium are examples of bioinert materials that are part of these bioceramics. When produced at nanoscale scales, these materials have a larger surface area and better cell adhesion. This review paper will go into great detail on the bioinert, bioresorbable, and bioactive nanoceramics-reinforced chitosan scaffolds for bone tissue engineering.
{"title":"Chitosan-incorporated Bioceramic-based Nanomaterials for Localized Release of Therapeutics and Bone Regeneration: An Overview of Recent Advances and Progresses","authors":"Sajad Safarzadeh, M. R. Mozafari, S. M. Naghib","doi":"10.2174/0113852728304647240426201554","DOIUrl":"https://doi.org/10.2174/0113852728304647240426201554","url":null,"abstract":"\u0000\u0000The usage of nanoparticles in tissue engineering applications has increased significantly in the last\u0000several years. Functional tissues are developed by regulating cell proliferation, differentiation, and migration on\u0000nanostructured scaffolds containing cells. These scaffolds provide an environment that is more structurally supportive\u0000than the microarchitecture of natural bone. Given its exceptional properties, such as its osteogenic potential,\u0000biocompatibility, and biodegradability, chitosan is a good and promising biomaterial. Unfortunately,\u0000chitosan's low mechanical strength makes it unsuitable for load-bearing applications. By mixing chitosan with\u0000other biomaterials, this drawback might be mitigated. Bone tissue engineering uses both bioresorbable materials\u0000like tricalcium phosphate and bioactive materials like hydroxyapatite and bioglass. Alumina and titanium are\u0000examples of bioinert materials that are part of these bioceramics. When produced at nanoscale scales, these\u0000materials have a larger surface area and better cell adhesion. This review paper will go into great detail on the\u0000bioinert, bioresorbable, and bioactive nanoceramics-reinforced chitosan scaffolds for bone tissue engineering.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140984069","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 : 2024-05-13DOI: 10.2174/0113852728294270240425093501
Debora Inacio Leite, Luiz Claudio Ferreira Pimentel, Maria da Conceição Avelino Dias, Monica Macedo Bastos, N. Boechat
Friedel-Crafts acylation (FCAcyl) is the most widespread method used to prepare aryl ketones and aldehydes. However, depending on the type of group attached to the benzene, their derivatives influence the electronic characteristics and structural orientations of the compounds during acylation; thus, the groups are very important for the success of the reaction. The existence of strong electron-donating groups, such as polyhydroxy/ polyalkoxyphenols and anilines on the aromatic ring, makes this reaction difficult. To overcome these problems and with the aim of obtaining aromatic ketones from benzene compounds, appropriate methodologies were described. Therefore, this review consists of showing the importance and applicability of the Houben- Hoesch and Sugasawa reactions as alternatives for the Friedel-Crafts acylation of polyhydroxy/ polyalkoxyphenols and anilines, respectively. The main advances used in the original methodologies were also described. The use of these reactions as an alternative to the renowned Friedel-Crafts acylation reactions should be taken into consideration as an important synthetic tool because there is the possibility of reducing steps, with consequent improvement of yield, in addition to optimizing reaction performance.
{"title":"Alternative Reactions to Friedel-crafts Acylation on Highly Activated Substrates","authors":"Debora Inacio Leite, Luiz Claudio Ferreira Pimentel, Maria da Conceição Avelino Dias, Monica Macedo Bastos, N. Boechat","doi":"10.2174/0113852728294270240425093501","DOIUrl":"https://doi.org/10.2174/0113852728294270240425093501","url":null,"abstract":"\u0000\u0000Friedel-Crafts acylation (FCAcyl) is the most widespread method used to prepare aryl ketones and\u0000aldehydes. However, depending on the type of group attached to the benzene, their derivatives influence the\u0000electronic characteristics and structural orientations of the compounds during acylation; thus, the groups are\u0000very important for the success of the reaction. The existence of strong electron-donating groups, such as polyhydroxy/\u0000polyalkoxyphenols and anilines on the aromatic ring, makes this reaction difficult. To overcome these\u0000problems and with the aim of obtaining aromatic ketones from benzene compounds, appropriate methodologies\u0000were described. Therefore, this review consists of showing the importance and applicability of the Houben-\u0000Hoesch and Sugasawa reactions as alternatives for the Friedel-Crafts acylation of polyhydroxy/\u0000polyalkoxyphenols and anilines, respectively. The main advances used in the original methodologies\u0000were also described. The use of these reactions as an alternative to the renowned Friedel-Crafts acylation reactions\u0000should be taken into consideration as an important synthetic tool because there is the possibility of reducing\u0000steps, with consequent improvement of yield, in addition to optimizing reaction performance.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140982924","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 : 2024-05-13DOI: 10.2174/0113852728310974240424080252
Bubun Banerjee, Arvind Singh, A. Priya, M. Kaur, Aditi Sharma
Nowadays, polyheterocyclic moieties are playing an important role in drug discovery. Many natural products contain a wide variety of polyheterocycles. Very recently among many other polyheterocycles, benzo[a]phenazine skeleton has gained huge attention due to their broad range of pharmacological efficacies which include anti-plasmodial, antitumor, antimalarial, anticancer, etc. activities. Interestingly, benzo[a]phenazin-5-ol derivatives have been used further as a template for the synthesis of structurally diverse biologically promising polyheterocycles under various reaction conditions. In this review, we have summarized all the recent developments related to the synthesis of structurally diverse biologically promising polyheterocycles involving benzo[a]phenazin-5-ol as a starting reagent or as an intermediate.
{"title":"Synthesis of Structurally Diverse and Biologically Promising Polyheterocycles Involving Benzo[a]phenazin-5-ols","authors":"Bubun Banerjee, Arvind Singh, A. Priya, M. Kaur, Aditi Sharma","doi":"10.2174/0113852728310974240424080252","DOIUrl":"https://doi.org/10.2174/0113852728310974240424080252","url":null,"abstract":"\u0000\u0000Nowadays, polyheterocyclic moieties are playing an important role in drug discovery.\u0000Many natural products contain a wide variety of polyheterocycles. Very recently\u0000among many other polyheterocycles, benzo[a]phenazine skeleton has gained huge attention\u0000due to their broad range of pharmacological efficacies which include anti-plasmodial, antitumor,\u0000antimalarial, anticancer, etc. activities. Interestingly, benzo[a]phenazin-5-ol derivatives\u0000have been used further as a template for the synthesis of structurally diverse biologically\u0000promising polyheterocycles under various reaction conditions. In this review, we have\u0000summarized all the recent developments related to the synthesis of structurally diverse biologically\u0000promising polyheterocycles involving benzo[a]phenazin-5-ol as a starting reagent\u0000or as an intermediate.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140984242","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 : 2024-05-09DOI: 10.2174/0113852728297985240408062346
Zahra Movahed, Hassan Valizadeh, Farzaneh Mirzaei
: Polysubstituted pyridine derivatives were producedwith high to excellent yields in the presence of nitrogen-doped graphene (NDG) as a dual acid–based catalyst. NDG efficiently catalyzes the multicomponent reaction between arylaldehydes, diethyl-acetylene dicarboxylates, malononitrile, and ammonium acetate under solvent-free conditions at 80°C to afford the polysubstituted pyridines in short reaction times. The structures of the synthesized pyridines were established by Ft-IR, 1H, and 13C NMR spectroscopic analysis. The advantages of this method include the in-situ oxidation of prepared 1,4-dihydropyridines, one-pot procedure, solventless system, operational simplicity, and no column chromatography. Additionally, neither toxic solvents nor catalysts are needed, and the procedure can be very reliable among the reported methodologies. The yields and reaction times in the presence of four times recycled catalyst are in comparable to the fresh catalyst. background: Graphene quantum dots have attracted considerable attention of chemists because of their unique properties such as: stability, non-toxicity, good water solubility, biocompatibility. In continuation of our interest in using ionic liquids, water or solvent-free systems as green reaction media in organic reactions for the synthesis of important compounds , we wish to report here efficient synthesis of polysubstituted pyridine derivatives in high to excellent yields using Nitrogen-doped graphene as efficient catalyst.
{"title":"Synthesis of Polysubstituted Pyridines via Nitrogen-doped Graphene Catalyzed One-Pot Multicomponent Reaction under Solvent-Free Conditions","authors":"Zahra Movahed, Hassan Valizadeh, Farzaneh Mirzaei","doi":"10.2174/0113852728297985240408062346","DOIUrl":"https://doi.org/10.2174/0113852728297985240408062346","url":null,"abstract":": Polysubstituted pyridine derivatives were producedwith high to excellent yields in the presence of nitrogen-doped graphene (NDG) as a dual acid–based catalyst. NDG efficiently catalyzes the multicomponent reaction between arylaldehydes, diethyl-acetylene dicarboxylates, malononitrile, and ammonium acetate under solvent-free conditions at 80°C to afford the polysubstituted pyridines in short reaction times. The structures of the synthesized pyridines were established by Ft-IR, 1H, and 13C NMR spectroscopic analysis. The advantages of this method include the in-situ oxidation of prepared 1,4-dihydropyridines, one-pot procedure, solventless system, operational simplicity, and no column chromatography. Additionally, neither toxic solvents nor catalysts are needed, and the procedure can be very reliable among the reported methodologies. The yields and reaction times in the presence of four times recycled catalyst are in comparable to the fresh catalyst. background: Graphene quantum dots have attracted considerable attention of chemists because of their unique properties such as: stability, non-toxicity, good water solubility, biocompatibility. In continuation of our interest in using ionic liquids, water or solvent-free systems as green reaction media in organic reactions for the synthesis of important compounds , we wish to report here efficient synthesis of polysubstituted pyridine derivatives in high to excellent yields using Nitrogen-doped graphene as efficient catalyst.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140937423","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 : 2024-05-06DOI: 10.2174/0113852728306541240409034052
Shan Jiang, Miao Wang
: Recently, the concept of mechanoredox chemistry has been proposed and well-developed in organic synthesis. Mechanoredox chemistry is conceptually similar to a photocatalyst reaction system, where piezoelectric materials are introduced to the reaction system in a manner analogous to photoredox catalysis. These reactions feature the ability to generate high-value radicals that do not require harsh reaction conditions of anhydrous and anaerobic conditions, an expensive photocatalyst, and the use of solvents, which renders these transformations highly industrially applicable. In addition, mechanoredox chemistry is also an emerging interdisciplinary research field that combines material chemistry with synthetic chemistry to create more useful reactions. This review provides a comprehensive summary of progress to date in the specific transformation and related mechanisms of piezoelectric-mediated mechanoredox reactions by ball milling in organic synthesis.
{"title":"A Review on Piezoelectric-Mediated Mechanoredox Reactions by Ball Milling in Organic Synthesis","authors":"Shan Jiang, Miao Wang","doi":"10.2174/0113852728306541240409034052","DOIUrl":"https://doi.org/10.2174/0113852728306541240409034052","url":null,"abstract":": Recently, the concept of mechanoredox chemistry has been proposed and well-developed in organic synthesis. Mechanoredox chemistry is conceptually similar to a photocatalyst reaction system, where piezoelectric materials are introduced to the reaction system in a manner analogous to photoredox catalysis. These reactions feature the ability to generate high-value radicals that do not require harsh reaction conditions of anhydrous and anaerobic conditions, an expensive photocatalyst, and the use of solvents, which renders these transformations highly industrially applicable. In addition, mechanoredox chemistry is also an emerging interdisciplinary research field that combines material chemistry with synthetic chemistry to create more useful reactions. This review provides a comprehensive summary of progress to date in the specific transformation and related mechanisms of piezoelectric-mediated mechanoredox reactions by ball milling in organic synthesis.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884953","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}
: Azepine is a privileged nitrogen-containing ring that has been found to display a wide range of biological activities. Azepine is a valuable skeleton in designing novel compounds in medicinal chemistry due to its interesting chemical and biological properties. The study on the synthesis of this ring system engenders a fascinating area of research owing to its potential to form an active pharmacophore for De Novo exploration. In this study, conventional and domino results were compared to access the diverse set of azepines in high yield. The domino approach has revolutionized the way through which the previously impossible yet significant transformations could be conceptualized, allowing the construction of difficult materials in one step. The aim of the present mini-review is to highlight the importance of the one-pot domino reaction for the synthesis of condensed azepines. This review also presents research on this subject from the past two decades.
{"title":"One-Pot Synthesis of Condensed Azepines","authors":"Khushboo Bhardwaj, Shivangi Jaiswal, Annu Bhardwaj, Dharma Kishore, Jaya Dwivedi, Swapnil Sharma","doi":"10.2174/0113852728300551240408054904","DOIUrl":"https://doi.org/10.2174/0113852728300551240408054904","url":null,"abstract":": Azepine is a privileged nitrogen-containing ring that has been found to display a wide range of biological activities. Azepine is a valuable skeleton in designing novel compounds in medicinal chemistry due to its interesting chemical and biological properties. The study on the synthesis of this ring system engenders a fascinating area of research owing to its potential to form an active pharmacophore for De Novo exploration. In this study, conventional and domino results were compared to access the diverse set of azepines in high yield. The domino approach has revolutionized the way through which the previously impossible yet significant transformations could be conceptualized, allowing the construction of difficult materials in one step. The aim of the present mini-review is to highlight the importance of the one-pot domino reaction for the synthesis of condensed azepines. This review also presents research on this subject from the past two decades.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884871","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 : 2024-05-06DOI: 10.2174/0113852728304619240408045311
Marcio C. S. de Mattos
: Trihaloisocyanuric acids [1,3,5-trihalo-1,3,5-triazine-2,4,6-(1H,3H,5H)-triones] are commercially available or easily prepared solids. They are highly reactive, stable, easily handled, and have an excellent atom economy, transferring up to three halogen atoms to organic substrates. In these regards, the present review summarizes their synthetic applications as safe and convenient reagents. Therefore, electrophilic halogenation reactions of alkenes, alkynes, arenes, heteroarenes, carbonyl compounds, and heteroatoms, as well as radical halogenation involving saturated substrates and in situ halogenated intermediates for Appel-type reactions are presented and discussed. Remarkably, applications of trihaloisocyanuric acids in processes for the construction of heteroarene scaffolds based on electrophilic halo- and oxidative cyclization, multicomponent reactions, and telescopic reactions are also given.
{"title":"Trihaloisocyanuric Acids: Useful Reagents for Halogenation Reactions and Heterocyclic Scaffold Construction","authors":"Marcio C. S. de Mattos","doi":"10.2174/0113852728304619240408045311","DOIUrl":"https://doi.org/10.2174/0113852728304619240408045311","url":null,"abstract":": Trihaloisocyanuric acids [1,3,5-trihalo-1,3,5-triazine-2,4,6-(1H,3H,5H)-triones] are commercially available or easily prepared solids. They are highly reactive, stable, easily handled, and have an excellent atom economy, transferring up to three halogen atoms to organic substrates. In these regards, the present review summarizes their synthetic applications as safe and convenient reagents. Therefore, electrophilic halogenation reactions of alkenes, alkynes, arenes, heteroarenes, carbonyl compounds, and heteroatoms, as well as radical halogenation involving saturated substrates and in situ halogenated intermediates for Appel-type reactions are presented and discussed. Remarkably, applications of trihaloisocyanuric acids in processes for the construction of heteroarene scaffolds based on electrophilic halo- and oxidative cyclization, multicomponent reactions, and telescopic reactions are also given.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884951","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 : 2024-05-06DOI: 10.2174/0113852728304549240328064426
Radell Echemendía, Kauê C. Capellaro, Antonio C. B. Burtoloso
: Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical reactions have become indispensable tools for accessing complex molecular structures, such as pharmaceuticals and natural products. The ability of sulfur ylides to participate in these diverse processes has made them indispensable tools in the synthetic chemist's toolbox. The use of sulfur ylides in photochemical transformations has garnered significant attention in the synthetic organic chemistry community, and they serve as powerful intermediates in several chemical transformations. This review article presents a comprehensive overview of the photochemical reactions mediated by sulfur ylides. Herein, we describe the key aspects of the reactivity of sulfur ylides in the presence of light. The reactivity of these compounds can be classified into three categories: sulfur ylides as energy acceptors, as electron donors, and as trapping reagents.
{"title":"Photochemical Reactions of Sulfur Ylides#","authors":"Radell Echemendía, Kauê C. Capellaro, Antonio C. B. Burtoloso","doi":"10.2174/0113852728304549240328064426","DOIUrl":"https://doi.org/10.2174/0113852728304549240328064426","url":null,"abstract":": Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical reactions have become indispensable tools for accessing complex molecular structures, such as pharmaceuticals and natural products. The ability of sulfur ylides to participate in these diverse processes has made them indispensable tools in the synthetic chemist's toolbox. The use of sulfur ylides in photochemical transformations has garnered significant attention in the synthetic organic chemistry community, and they serve as powerful intermediates in several chemical transformations. This review article presents a comprehensive overview of the photochemical reactions mediated by sulfur ylides. Herein, we describe the key aspects of the reactivity of sulfur ylides in the presence of light. The reactivity of these compounds can be classified into three categories: sulfur ylides as energy acceptors, as electron donors, and as trapping reagents.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140884874","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 : 2024-05-03DOI: 10.2174/0113852728239522231006064747
Stanisław Ostrowski, Sebastian Grzyb, Bartosz Godlewski
:: The synthesis of meso-tetraphenylporphyrin derivatives, double functionalized in one of the phenyl rings (with a nitro group and carbon substituents), is described. 5-(4- Nitroaryl)-10,15,20-triarylporphyrinates react, in the presence of a base (t-BuOK), with carbanions containing a leaving group at the carbanionic center to give products of substitution of hydrogen at ortho-position to the nitro group via vicarious nucleophilic substitution scheme. Their alkylation with allyl bromide or 4-bromobut-1-en (t-BuOK/DMF, at 0-5°C) leads to porphyrins bearing side alkyl chain with a terminal double bond in yields of up to 82%. The double-substituted intermediates are very convenient substrates for Heck cross-coupling reactions. In this study, the synthesis of porphyrin–azulene dyads is reported. In some cases, the formation of highly conjugated systems is observed, with moderate yield. Their structures are interesting from both the porphyrin and azulene point of view.
{"title":"Some Terminally Alkenyl-substituted Porphyrins: Synthesis and Attempts of Heck Reaction Leading to Porphyrin-Azulene Dyads","authors":"Stanisław Ostrowski, Sebastian Grzyb, Bartosz Godlewski","doi":"10.2174/0113852728239522231006064747","DOIUrl":"https://doi.org/10.2174/0113852728239522231006064747","url":null,"abstract":":: The synthesis of meso-tetraphenylporphyrin derivatives, double functionalized in one of the phenyl rings (with a nitro group and carbon substituents), is described. 5-(4- Nitroaryl)-10,15,20-triarylporphyrinates react, in the presence of a base (t-BuOK), with carbanions containing a leaving group at the carbanionic center to give products of substitution of hydrogen at ortho-position to the nitro group via vicarious nucleophilic substitution scheme. Their alkylation with allyl bromide or 4-bromobut-1-en (t-BuOK/DMF, at 0-5°C) leads to porphyrins bearing side alkyl chain with a terminal double bond in yields of up to 82%. The double-substituted intermediates are very convenient substrates for Heck cross-coupling reactions. In this study, the synthesis of porphyrin–azulene dyads is reported. In some cases, the formation of highly conjugated systems is observed, with moderate yield. Their structures are interesting from both the porphyrin and azulene point of view.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840104","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 : 2024-05-03DOI: 10.2174/0113852728299375240405053207
Silvia E. Loredo-Carrillo, Elisa Leyva, Lluvia Itzel López-López, Gabriela Navarro-Tovar, Denisse de Loera, Sarai Vega-Rodríguez
: An alternative to finding new drugs for the treatment of various diseases is the chemical modification of the structure of compounds of natural origin. Among them, naphthoquinones are very interesting candidates, as they are antibacterial, antifungal, antiparasitic, and anticancer agents. Naphthoquinones are redox compounds that can accept one or two electrons, generating reactive oxygen species in the cell and producing cell apoptosis. Naphthoquinones are unsaturated compounds containing a dicarbonyl sequence in the para position, which is highly reactive. Several studies of the chemical modification of naphthoquinones, either of natural origin (such as lapachol or juglone) or synthetic origin, have demonstrated the great importance and versatility of this type of compound. Polyhydroxylated derivatives, amino, thioethers, and conjugated heterosystems (indole or pyrrole groups) have been synthesized. Depending on the type of derivative, their specific use against certain types of microorganisms or cancer cell lines has been demonstrated.
{"title":"Description of Some Methodologies for the Synthesis of 1,4-Naphthoquinone Derivatives and Examples of their Biological Activity: A Review","authors":"Silvia E. Loredo-Carrillo, Elisa Leyva, Lluvia Itzel López-López, Gabriela Navarro-Tovar, Denisse de Loera, Sarai Vega-Rodríguez","doi":"10.2174/0113852728299375240405053207","DOIUrl":"https://doi.org/10.2174/0113852728299375240405053207","url":null,"abstract":": An alternative to finding new drugs for the treatment of various diseases is the chemical modification of the structure of compounds of natural origin. Among them, naphthoquinones are very interesting candidates, as they are antibacterial, antifungal, antiparasitic, and anticancer agents. Naphthoquinones are redox compounds that can accept one or two electrons, generating reactive oxygen species in the cell and producing cell apoptosis. Naphthoquinones are unsaturated compounds containing a dicarbonyl sequence in the para position, which is highly reactive. Several studies of the chemical modification of naphthoquinones, either of natural origin (such as lapachol or juglone) or synthetic origin, have demonstrated the great importance and versatility of this type of compound. Polyhydroxylated derivatives, amino, thioethers, and conjugated heterosystems (indole or pyrrole groups) have been synthesized. Depending on the type of derivative, their specific use against certain types of microorganisms or cancer cell lines has been demonstrated.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840113","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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