Pub Date : 2024-05-02DOI: 10.2174/0113852728304402240403052919
Claudio J.A. Mota
: This mini-review reports the current routes used for the production of dimethyl carbonate (DMC), a green and versatile methylating reactant widely used in organic synthesis. The use of DMC in methylation processes is also discussed. The main routes of DMC production, encompassing the reaction between phosgene and methanol and the oxidative carbonylation of methanol with CO and urea methanolysis, are summarised. However, none of them can be considered entirely green, and the drawbacks in terms of green chemistry principles are addressed. The present commercial route to DMC, which involves the initial reaction of CO2 with ethylene oxide to produce ethylene carbonate that further reacts with excess methanol, is also explored regarding the green chemistry principles. Moreover, this review focuses on the direct DMC production from the reaction of methanol and CO2, discussing catalysts and strategies to shift equilibrium. An emphasis is given to heterogeneous catalysts, especially those based on CeO2. A final remark on the production of DMC through the capture of CO2 using chitosan-derived adsorbents and renewable methanol is addressed.
{"title":"Green Routes to Dimethyl Carbonate: A Green and Versatile Methylating Reactant","authors":"Claudio J.A. Mota","doi":"10.2174/0113852728304402240403052919","DOIUrl":"https://doi.org/10.2174/0113852728304402240403052919","url":null,"abstract":": This mini-review reports the current routes used for the production of dimethyl carbonate (DMC), a green and versatile methylating reactant widely used in organic synthesis. The use of DMC in methylation processes is also discussed. The main routes of DMC production, encompassing the reaction between phosgene and methanol and the oxidative carbonylation of methanol with CO and urea methanolysis, are summarised. However, none of them can be considered entirely green, and the drawbacks in terms of green chemistry principles are addressed. The present commercial route to DMC, which involves the initial reaction of CO2 with ethylene oxide to produce ethylene carbonate that further reacts with excess methanol, is also explored regarding the green chemistry principles. Moreover, this review focuses on the direct DMC production from the reaction of methanol and CO2, discussing catalysts and strategies to shift equilibrium. An emphasis is given to heterogeneous catalysts, especially those based on CeO2. A final remark on the production of DMC through the capture of CO2 using chitosan-derived adsorbents and renewable methanol is addressed.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840353","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 : 2024-04-30DOI: 10.2174/0113852728300401240404063340
Pooja Daga, Nilanjan Dey
: Organomercuric species pose significant environmental and health risks, requiring precise detection methods for effective monitoring and risk assessment. Current approaches in multiple material-based sensing of organomercuric species and their discrimination over inorganic Hg2+ ions are reviewed in this paper. These approaches include the use of diverse sensing materials, such as small-molecule-based optical probes, nanoparticles or nanocomposite-based optical probes, electrochemical-based probes, fluorescent probes, colorimetric indicators, and some other probes. The significance and application of these materials, along with the sensing strategy of organomercury species and their mechanism, were also interpreted. This review article presents a comprehensive overview of recent advancements in optoelectronic sensing techniques for the discrimination of organomercuric species from inorganic mercury compounds. Optoelectronic sensors, leveraging the principles of optics and electronics, offer enhanced sensitivity, selectivity, and real-time monitoring capabilities. The paper discusses the advantages and limitations of each sensing technique and highlights the recent advancements in material synthesis and design, which have led to the development of highly sensitive and selective sensors for organomercury compounds. Furthermore, the discrimination of organomercuric species from inorganic Hg2+ ions is emphasized, which is a challenging task due to their similar chemical properties. Overall, this review article provides an overview of the current state-of-the-art in multiple material-based sensing of organomercuric species and its discrimination from inorganic Hg2+ ions, which can aid in the development of novel sensing strategies for environmental and biomedical applications.
{"title":"Recent Development in Optoelectronic Sensing of Organomercuric Species and its Discrimination Over Inorganic Mercury","authors":"Pooja Daga, Nilanjan Dey","doi":"10.2174/0113852728300401240404063340","DOIUrl":"https://doi.org/10.2174/0113852728300401240404063340","url":null,"abstract":": Organomercuric species pose significant environmental and health risks, requiring precise detection methods for effective monitoring and risk assessment. Current approaches in multiple material-based sensing of organomercuric species and their discrimination over inorganic Hg2+ ions are reviewed in this paper. These approaches include the use of diverse sensing materials, such as small-molecule-based optical probes, nanoparticles or nanocomposite-based optical probes, electrochemical-based probes, fluorescent probes, colorimetric indicators, and some other probes. The significance and application of these materials, along with the sensing strategy of organomercury species and their mechanism, were also interpreted. This review article presents a comprehensive overview of recent advancements in optoelectronic sensing techniques for the discrimination of organomercuric species from inorganic mercury compounds. Optoelectronic sensors, leveraging the principles of optics and electronics, offer enhanced sensitivity, selectivity, and real-time monitoring capabilities. The paper discusses the advantages and limitations of each sensing technique and highlights the recent advancements in material synthesis and design, which have led to the development of highly sensitive and selective sensors for organomercury compounds. Furthermore, the discrimination of organomercuric species from inorganic Hg2+ ions is emphasized, which is a challenging task due to their similar chemical properties. Overall, this review article provides an overview of the current state-of-the-art in multiple material-based sensing of organomercuric species and its discrimination from inorganic Hg2+ ions, which can aid in the development of novel sensing strategies for environmental and biomedical applications.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140840110","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 : 2024-04-27DOI: 10.2174/0113852728313247240417080211
Tapas Ghosh
: Research on novel discotic molecules, which consist of a rigid core with flexible peripheral chains, has gained much attention due to their crucial role as organic photovoltaic materials, organic field-effect transistors, and semiconductors for photocurrent generation, as well as the possibility of their other optoelectronic applications. This review article describes the developments in fundamental design ideas and synthetic approaches of porphyrin-based meso and beta-substituted liquid crystals. In addition, the current review highlights the various structural alterations made by the researchers in the field of porphyrin-based mesogens and changes in properties, both for materials intended for commercially successful liquid crystal displays, including other applications, and for more basic purposes of demonstrating structure-property relationships.
{"title":"Synthesis, Thermotropic Properties, and Applications of Porphyrin-based Liquid Crystals: A Comprehensive Review","authors":"Tapas Ghosh","doi":"10.2174/0113852728313247240417080211","DOIUrl":"https://doi.org/10.2174/0113852728313247240417080211","url":null,"abstract":": Research on novel discotic molecules, which consist of a rigid core with flexible peripheral chains, has gained much attention due to their crucial role as organic photovoltaic materials, organic field-effect transistors, and semiconductors for photocurrent generation, as well as the possibility of their other optoelectronic applications. This review article describes the developments in fundamental design ideas and synthetic approaches of porphyrin-based meso and beta-substituted liquid crystals. In addition, the current review highlights the various structural alterations made by the researchers in the field of porphyrin-based mesogens and changes in properties, both for materials intended for commercially successful liquid crystal displays, including other applications, and for more basic purposes of demonstrating structure-property relationships.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140812415","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 : 2024-04-24DOI: 10.2174/0113852728296687240328080900
Neetu Rajpoot, Dinesh Puri
A natural and renewable substrate for the synthesis of high-performance macromolecules is polysaccharides. Grafting with the use of microwaves of synthetic polymers onto natural polysaccharides is a common, adaptable, and practical method of creating materials based on polysaccharides. It eliminates all drawbacks of the traditional grafting technique, including the need for hazardous solvents and longer reaction times. Grafting yield is also increased by microwave irradiation. In fact, the employment of microwaves in polysaccharide grafting modification for diverse applications has been prompted by the growing interest in clean and environment- friendly chemistry. Furthermore, compared with their traditionally synthesized counterparts, microwavesynthesized polysaccharide copolymers frequently have greater characteristics for commercial exploitation. Moreover, for many traditional grafting processes, the necessity for an inert environment is an additional drawback, which can be overcome by microwave grafting techniques. This study focuses on the current use of microwave heating in polysaccharide grafting modifications and its further use in pharmaceutical formulations.
{"title":"Microwave Assisted Grafting Technique for Modification of Polysaccharides","authors":"Neetu Rajpoot, Dinesh Puri","doi":"10.2174/0113852728296687240328080900","DOIUrl":"https://doi.org/10.2174/0113852728296687240328080900","url":null,"abstract":"\u0000\u0000A natural and renewable substrate for the synthesis of high-performance macromolecules is polysaccharides.\u0000Grafting with the use of microwaves of synthetic polymers onto natural polysaccharides is a common,\u0000adaptable, and practical method of creating materials based on polysaccharides. It eliminates all drawbacks of\u0000the traditional grafting technique, including the need for hazardous solvents and longer reaction times. Grafting\u0000yield is also increased by microwave irradiation. In fact, the employment of microwaves in polysaccharide\u0000grafting modification for diverse applications has been prompted by the growing interest in clean and environment-\u0000friendly chemistry. Furthermore, compared with their traditionally synthesized counterparts, microwavesynthesized\u0000polysaccharide copolymers frequently have greater characteristics for commercial exploitation.\u0000Moreover, for many traditional grafting processes, the necessity for an inert environment is an additional drawback,\u0000which can be overcome by microwave grafting techniques. This study focuses on the current use of microwave\u0000heating in polysaccharide grafting modifications and its further use in pharmaceutical formulations.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140661918","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 : 2024-04-24DOI: 10.2174/0113852728252737240327041634
Ting-Ting Wu, Wengui Wang
2,3-Dihydrobenzofuran and coumaranone are readily available in numerous naturally occurring compounds. They mostly exist in plenty of food plants and medicinal plants. Such compounds constitute a series of flavor components and bioactive molecules. Their preparation has been an attractive field of research. In the past few decades, great efforts have been made in the preparation of the 2,3-dihydrobenzofuran structure through both metal-catalyzed and organocatalyzed ways. Visible light-promoted reactions sprang up in the early 21st century and represent a green manner of transformations. Under the irradiation of visible light, radicals could be generated under milder conditions. Thus, visible light-promoted reactions spread widely in the field of chemical synthesis. In recent years, visible light-promoted preparation of 2,3-dihydrobenzofuran and coumaranone has been developed by different groups, including both intramolecular and intermolecular reactions. The benign reaction conditions allow better functional group-tolerance and lead to diverse structures. Several reviews on the synthesis of 2,3-dihydrobenzofuran have been reported. However, visible light-promoted approaches to such structures have not been well reviewed. Our review will cover the literature that has been reported on the discovery of 2,3-dihydrobenzofuran in food and visible light-promoted preparation of 2,3- dihydrobenzofuran, attempting to summarize the existing methods and provide guidance to the chemists on the present challenges.
{"title":"Visible Light-Promoted Preparation of 2,3-Dihydrobenzofurans and Coumaranones","authors":"Ting-Ting Wu, Wengui Wang","doi":"10.2174/0113852728252737240327041634","DOIUrl":"https://doi.org/10.2174/0113852728252737240327041634","url":null,"abstract":"\u0000\u00002,3-Dihydrobenzofuran and coumaranone are readily available in numerous naturally occurring\u0000compounds. They mostly exist in plenty of food plants and medicinal plants. Such compounds constitute a series\u0000of flavor components and bioactive molecules. Their preparation has been an attractive field of research. In\u0000the past few decades, great efforts have been made in the preparation of the 2,3-dihydrobenzofuran structure\u0000through both metal-catalyzed and organocatalyzed ways. Visible light-promoted reactions sprang up in the early\u000021st century and represent a green manner of transformations. Under the irradiation of visible light, radicals\u0000could be generated under milder conditions. Thus, visible light-promoted reactions spread widely in the field of\u0000chemical synthesis. In recent years, visible light-promoted preparation of 2,3-dihydrobenzofuran and coumaranone\u0000has been developed by different groups, including both intramolecular and intermolecular reactions. The\u0000benign reaction conditions allow better functional group-tolerance and lead to diverse structures. Several reviews\u0000on the synthesis of 2,3-dihydrobenzofuran have been reported. However, visible light-promoted approaches\u0000to such structures have not been well reviewed. Our review will cover the literature that has been reported\u0000on the discovery of 2,3-dihydrobenzofuran in food and visible light-promoted preparation of 2,3-\u0000dihydrobenzofuran, attempting to summarize the existing methods and provide guidance to the chemists on the\u0000present challenges.\u0000","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140663653","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 : 2024-04-17DOI: 10.2174/0113852728303189240321084818
Dileep Kumar Singh, Haider Iqbal, Mohd Ayub Ansari
:: In recent times, many research groups have focused their attention on nitrogen-containing heterocyclic compounds with the aim of gaining a deeper understanding of their biological characteristics. Among them, molecules based on 1,2,3-triazole and benzimidazole have exhibited diverse biological applications and are present in many drug molecules. The purpose of this review is to describe various benzimidazole-1,2,3-triazole hybrids and to provide a comprehensive evaluation of their biological properties. The compounds discussed in this study have been synthesized through a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction between diverse azides and alkynes, utilizing a 1,2,3-triazole scaffold as a linkage between two connecting groups. The synthesis of several benzimidazole-1,2,3-triazole hybrids is covered in this review, along with a biological assessment of their anticancer, antiproliferative, antitubercular, antibacterial, antidepressant, and other activities. Moreover, in our opinion, this review may be useful for the development of various medicinally significant molecules.
{"title":"Recent Progress in the Synthesis and Biological Assessment of Benzimidazole-1,2,3- Triazole Hybrids","authors":"Dileep Kumar Singh, Haider Iqbal, Mohd Ayub Ansari","doi":"10.2174/0113852728303189240321084818","DOIUrl":"https://doi.org/10.2174/0113852728303189240321084818","url":null,"abstract":":: In recent times, many research groups have focused their attention on nitrogen-containing heterocyclic compounds with the aim of gaining a deeper understanding of their biological characteristics. Among them, molecules based on 1,2,3-triazole and benzimidazole have exhibited diverse biological applications and are present in many drug molecules. The purpose of this review is to describe various benzimidazole-1,2,3-triazole hybrids and to provide a comprehensive evaluation of their biological properties. The compounds discussed in this study have been synthesized through a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction between diverse azides and alkynes, utilizing a 1,2,3-triazole scaffold as a linkage between two connecting groups. The synthesis of several benzimidazole-1,2,3-triazole hybrids is covered in this review, along with a biological assessment of their anticancer, antiproliferative, antitubercular, antibacterial, antidepressant, and other activities. Moreover, in our opinion, this review may be useful for the development of various medicinally significant molecules.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140612264","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}
: Organocatalyst 1,4-diazabicyclo [2.2.2]octane (DABCO) has proven to be an efficient and environmentally friendly catalyst in the multicomponent reaction involving aldehydes, ethylenediamine, and thioglycolic acid under microwave conditions. DABCO stands out among other organic catalysts due to its costeffectiveness, non-toxic nature, and environmentally conscious profile. The method employed in this study exhibited exceptional attributes, such as high yields, swift reaction times, atom economy, catalyst reusability, and minimal catalyst loading. Additionally, there were excellent yields of products (90-94%). The melting points, UV-Vis, IR, 1HNMR, 13CNMR, were used to analyze the produced compounds. The in-vitro antibacterial activity of the synthesized compounds was investigated against pathogenic strains E. coli and Bacillus supstalis, and the results obtained were further explained with the help of DFT and molecular orbital calculations. Moreover, the compound 4b was found to be the most potent antibacterial agent amongst all tested compounds. result: Bis-thiazolidinones derivatives have been synthesized in excellent yields (90–94%) by mixing of aldehydes (2 mmol), ethylenediamine (1 mmol), thioglycolic acid (2 mmol), using DABCO (0.5 mmol), in 8 to 10 minutes under microwave irradiation.
{"title":"Organocatalyst 1,4-diazabicyclo [2.2.2]Octane (DABCO)-Catalyzed Sustainable Synthesis of Bis-Thiazolidinones Derivatives and their Spectral and DFT Analysis","authors":"Saloni Sahal, Mamta Chahar, Har Lal Singh, Renu Bishnoi, Sarita Khaturia","doi":"10.2174/0113852728304587240319061348","DOIUrl":"https://doi.org/10.2174/0113852728304587240319061348","url":null,"abstract":": Organocatalyst 1,4-diazabicyclo [2.2.2]octane (DABCO) has proven to be an efficient and environmentally friendly catalyst in the multicomponent reaction involving aldehydes, ethylenediamine, and thioglycolic acid under microwave conditions. DABCO stands out among other organic catalysts due to its costeffectiveness, non-toxic nature, and environmentally conscious profile. The method employed in this study exhibited exceptional attributes, such as high yields, swift reaction times, atom economy, catalyst reusability, and minimal catalyst loading. Additionally, there were excellent yields of products (90-94%). The melting points, UV-Vis, IR, 1HNMR, 13CNMR, were used to analyze the produced compounds. The in-vitro antibacterial activity of the synthesized compounds was investigated against pathogenic strains E. coli and Bacillus supstalis, and the results obtained were further explained with the help of DFT and molecular orbital calculations. Moreover, the compound 4b was found to be the most potent antibacterial agent amongst all tested compounds. result: Bis-thiazolidinones derivatives have been synthesized in excellent yields (90–94%) by mixing of aldehydes (2 mmol), ethylenediamine (1 mmol), thioglycolic acid (2 mmol), using DABCO (0.5 mmol), in 8 to 10 minutes under microwave irradiation.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140612351","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 : 2024-04-17DOI: 10.2174/0113852728294047240315063815
Muhammad Solehin Abd Ghani, Nur Ain Latifhaa Abu Bakar, Arba Pramundita Ramadani, Arde Toga Nugraha, Khalijah Awang, Mohammad Tasyriq Che Omar, Unang Supratman, Ezatul Ezleen Kamarulzaman, Mohamad Nurul Azmi Mohamad Taib
: A total of twelve pentacyclic triterpenoid derivatives based on betulin (1) and lupeol (2) scaffolds isolated from Diospyros foxworthyi were hemisynthesized by acylation or acetylation reactions with appropriate acid chloride or acetic anhydride. The structures of the hemisynthesised compounds were characterised by means of FT-IR, 1D- and 2D-NMR, as well as HRMS analysis. These compounds were assayed for in vitro anti-malarial studies by inhibition of β-hematin formation assay with chloroquine as a positive control. Compounds 1d and 2f showed the strongest potential as β-hematin formation inhibitors with IC50 values of 6.66 ± 1.36 and 11.89 ± 0.15 µM, respectively, compared with the positive control (chloroquine; IC50 = 37.50 ± 0.60 µM). In silico molecular docking simulations were performed using AutoDock Vina for compounds 1d and 2f to investigate the binding interactions and free energy of binding (FEB) with the hemozoin supercell crystal structure (CCDC number: XETXUP01). The findings revealed several hydrophobic interaction modes between the 1d, 2f and hemozoin, with calculated FEBs of -8.4 ± 0.2 and -8.9 ± 0.0 kcal mol-1 , indicating strong and favourable interactions.
{"title":"Hemisynthesis of Pentacyclic Triterpenoids from Diospyros foxworthyi with in vitro and in silico Anti-malarial Evaluation","authors":"Muhammad Solehin Abd Ghani, Nur Ain Latifhaa Abu Bakar, Arba Pramundita Ramadani, Arde Toga Nugraha, Khalijah Awang, Mohammad Tasyriq Che Omar, Unang Supratman, Ezatul Ezleen Kamarulzaman, Mohamad Nurul Azmi Mohamad Taib","doi":"10.2174/0113852728294047240315063815","DOIUrl":"https://doi.org/10.2174/0113852728294047240315063815","url":null,"abstract":": A total of twelve pentacyclic triterpenoid derivatives based on betulin (1) and lupeol (2) scaffolds isolated from Diospyros foxworthyi were hemisynthesized by acylation or acetylation reactions with appropriate acid chloride or acetic anhydride. The structures of the hemisynthesised compounds were characterised by means of FT-IR, 1D- and 2D-NMR, as well as HRMS analysis. These compounds were assayed for in vitro anti-malarial studies by inhibition of β-hematin formation assay with chloroquine as a positive control. Compounds 1d and 2f showed the strongest potential as β-hematin formation inhibitors with IC50 values of 6.66 ± 1.36 and 11.89 ± 0.15 µM, respectively, compared with the positive control (chloroquine; IC50 = 37.50 ± 0.60 µM). In silico molecular docking simulations were performed using AutoDock Vina for compounds 1d and 2f to investigate the binding interactions and free energy of binding (FEB) with the hemozoin supercell crystal structure (CCDC number: XETXUP01). The findings revealed several hydrophobic interaction modes between the 1d, 2f and hemozoin, with calculated FEBs of -8.4 ± 0.2 and -8.9 ± 0.0 kcal mol-1 , indicating strong and favourable interactions.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140612219","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 : 2024-04-17DOI: 10.2174/0113852728296619240321060646
Hélène Pellissier
:: The Nazarov reaction involves the cyclization of divinyl ketones into cyclopentenones under the influence of strong acids. The prevalence of five-membered carbocycles in a multitude of natural and bioactive products has triggered an intense development of efficient methods for their construction. In particular, asymmetric versions of the Nazarov reaction are achieved by using either a chiral auxiliary or a chiral catalyst, which can be an organocatalyst, a metal catalyst, or a multicatalytic system. This review aims to update the field of asymmetric Nazarov reactions published in 2017. It is divided into four sections, dealing successively with Nazarov reactions of chiral auxiliaries, organocatalytic enantioselective Nazarov reactions, metal/boron-catalyzed enantioselective Nazarov reactions, and multicatalytic enantioselective Nazarov reactions. Each section of the review is subdivided into simple asymmetric Nazarov reactions and Nazarovbased domino/tandem reactions, which have allowed numerous more complex functionalized chiral molecules to be synthesized in one-pot procedures.
{"title":"Recent Developments in Asymmetric Nazarov Reactions","authors":"Hélène Pellissier","doi":"10.2174/0113852728296619240321060646","DOIUrl":"https://doi.org/10.2174/0113852728296619240321060646","url":null,"abstract":":: The Nazarov reaction involves the cyclization of divinyl ketones into cyclopentenones under the influence of strong acids. The prevalence of five-membered carbocycles in a multitude of natural and bioactive products has triggered an intense development of efficient methods for their construction. In particular, asymmetric versions of the Nazarov reaction are achieved by using either a chiral auxiliary or a chiral catalyst, which can be an organocatalyst, a metal catalyst, or a multicatalytic system. This review aims to update the field of asymmetric Nazarov reactions published in 2017. It is divided into four sections, dealing successively with Nazarov reactions of chiral auxiliaries, organocatalytic enantioselective Nazarov reactions, metal/boron-catalyzed enantioselective Nazarov reactions, and multicatalytic enantioselective Nazarov reactions. Each section of the review is subdivided into simple asymmetric Nazarov reactions and Nazarovbased domino/tandem reactions, which have allowed numerous more complex functionalized chiral molecules to be synthesized in one-pot procedures.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140612263","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 : 2024-04-16DOI: 10.2174/0113852728295316240325041145
Hany M. Abd El-Lateef, Thomas Nady A. Eskander, Mohammad Saleh Hussein Alzubi, Mai M Khalaf, Mahmoud Abd El Aleem Ali Ali El-Remaily
: In the current study, a zinc-linked amino acid complex was successfully synthesized as an efficient and recoverable catalyst for the synthesis of dihydro pyrano thiazole derivatives via the reaction of an aromatic aldehyde with malononitrile and rhodanine in one-pot, three-component reaction under green conditions. The structures of the new compounds were elucidated by elemental and spectral analyses. Environmental friendliness, low cost, operational simplicity, extensive reusability and applicability, and easy recovery of the catalyst using simple methods are the critical features of this methodology. Moreover, a series of dihydro pyrano thiazole derivatives were synthesized. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, short reaction time, excellent yields, and high purity without using any hazardous solvents.
{"title":"Zn[L-proline]2 as an Efficient Catalyst for the Synthesis of Dihydro Pyrano Thiazole Derivatives via Cycloaddition Reaction in Aqueous Medium","authors":"Hany M. Abd El-Lateef, Thomas Nady A. Eskander, Mohammad Saleh Hussein Alzubi, Mai M Khalaf, Mahmoud Abd El Aleem Ali Ali El-Remaily","doi":"10.2174/0113852728295316240325041145","DOIUrl":"https://doi.org/10.2174/0113852728295316240325041145","url":null,"abstract":": In the current study, a zinc-linked amino acid complex was successfully synthesized as an efficient and recoverable catalyst for the synthesis of dihydro pyrano thiazole derivatives via the reaction of an aromatic aldehyde with malononitrile and rhodanine in one-pot, three-component reaction under green conditions. The structures of the new compounds were elucidated by elemental and spectral analyses. Environmental friendliness, low cost, operational simplicity, extensive reusability and applicability, and easy recovery of the catalyst using simple methods are the critical features of this methodology. Moreover, a series of dihydro pyrano thiazole derivatives were synthesized. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, short reaction time, excellent yields, and high purity without using any hazardous solvents.","PeriodicalId":10926,"journal":{"name":"Current Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-04-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140581410","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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