Pub Date : 2023-01-02DOI: 10.1080/17518253.2022.2153628
Courtney Carson, Joshua Hassing, Trinity Olguin, Karl P. Peterson, Rebecca A. Haley
ABSTRACT Reductive coupling reactions are a facile and versatile way to make carbon – carbon bonds. However, most methods within this class of reactions makes use of reprotoxic, amide-based solvents. Mechanochemistry, a method that does not always require solvent, has been used for reductive coupling methods but still reports the use of at least some amide-based solvent for productive outcomes. This work presents the reactivity trends for the reductive homocoupling of aryl iodides when using various amounts of N,N-dimethylformamide (a commonly used amide-based solvent) and dimethyl carbonate (a greener alternative). The results of these experiments show that dimethyl carbonate may be used in sub-stoichiometric amounts with equal or greater efficiency to N,N-dimethyl formamide. Further, cross-electrophile coupling (XEC) is explored with various solvents, showing that N-butyl pyrrolidinone is efficient as a liquid assisted grinding solvent. These experiments show that under mechanochemical conditions, safer solvents are able to be used with no loss of efficacy for reductive coupling reactions. GRAPHICAL ABSTRACT
{"title":"Reactivity trends for mechanochemical reductive coupling of aryl iodides","authors":"Courtney Carson, Joshua Hassing, Trinity Olguin, Karl P. Peterson, Rebecca A. Haley","doi":"10.1080/17518253.2022.2153628","DOIUrl":"https://doi.org/10.1080/17518253.2022.2153628","url":null,"abstract":"ABSTRACT Reductive coupling reactions are a facile and versatile way to make carbon – carbon bonds. However, most methods within this class of reactions makes use of reprotoxic, amide-based solvents. Mechanochemistry, a method that does not always require solvent, has been used for reductive coupling methods but still reports the use of at least some amide-based solvent for productive outcomes. This work presents the reactivity trends for the reductive homocoupling of aryl iodides when using various amounts of N,N-dimethylformamide (a commonly used amide-based solvent) and dimethyl carbonate (a greener alternative). The results of these experiments show that dimethyl carbonate may be used in sub-stoichiometric amounts with equal or greater efficiency to N,N-dimethyl formamide. Further, cross-electrophile coupling (XEC) is explored with various solvents, showing that N-butyl pyrrolidinone is efficient as a liquid assisted grinding solvent. These experiments show that under mechanochemical conditions, safer solvents are able to be used with no loss of efficacy for reductive coupling reactions. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"144 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2023-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88567337","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 : 2023-01-01Epub Date: 2022-12-22DOI: 10.1080/17518253.2022.2149280
Hua Zhao, Gary A Baker
Ionic liquids (ILs) have been widely explored as alternative solvents for carbon dioxide (CO2) capture and utilization. However, most of these processes are under pressures significantly higher than atmospheric level, which not only levies additional equipment and operation costs, but also makes the large-scale CO2 capture and conversion less practical. In this study, we rationally designed glycol ether-functionalized imidazolium, phosphonium and ammonium ILs containing acetate (OAc-) or Tf2N- anions, and found these task-specific ILs could solubilize up to 0.55 mol CO2 per mole of IL (or 5.9 wt% CO2) at room temperature and atmospheric pressure. Although acetate anions enabled a better capture of CO2, Tf2N- anions are more compatible with alcohol dehydrogenase (ADH), which is a key enzyme involved in the cascade enzymatic conversion of CO2 to methanol. Our promising results indicate the possibility of CO2 capture under ambient pressure and its enzymatic conversion to valuable commodity.
{"title":"Functionalized Ionic Liquids for CO<sub>2</sub> Capture under Ambient Pressure.","authors":"Hua Zhao, Gary A Baker","doi":"10.1080/17518253.2022.2149280","DOIUrl":"10.1080/17518253.2022.2149280","url":null,"abstract":"<p><p>Ionic liquids (ILs) have been widely explored as alternative solvents for carbon dioxide (CO<sub>2</sub>) capture and utilization. However, most of these processes are under pressures significantly higher than atmospheric level, which not only levies additional equipment and operation costs, but also makes the large-scale CO<sub>2</sub> capture and conversion less practical. In this study, we rationally designed glycol ether-functionalized imidazolium, phosphonium and ammonium ILs containing acetate (OAc<sup>-</sup>) or Tf<sub>2</sub>N<sup>-</sup> anions, and found these task-specific ILs could solubilize up to 0.55 mol CO<sub>2</sub> per mole of IL (or 5.9 wt% CO<sub>2</sub>) at room temperature and atmospheric pressure. Although acetate anions enabled a better capture of CO<sub>2</sub>, Tf<sub>2</sub>N<sup>-</sup> anions are more compatible with alcohol dehydrogenase (ADH), which is a key enzyme involved in the cascade enzymatic conversion of CO<sub>2</sub> to methanol. Our promising results indicate the possibility of CO<sub>2</sub> capture under ambient pressure and its enzymatic conversion to valuable commodity.</p>","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"16 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254919/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9629314","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2022-12-30DOI: 10.1080/17518253.2022.2158690
Ashleigh Naysmith, N. S. Mian, S. Rana
ABSTRACT Electronic textiles (e-textiles) are undergoing rapid technological advancements to attain e-textiles that look and feel like conventional textile fabrics. Research seeks to develop highly functionalized textile-based sensors, actuators, and energy storage devices that integrate seamlessly with current textile technologies. Presently, developments are limited by either low electrical performance, or high cost and complex construction. Additionally, negotiating the balance between high performing e-textiles and environmentally benign production is a challenge. In this report, green synthesized silver nanoparticles (AgNPs) are composited with the conjugated polymer, polypyrrole (Ppy), to create a low-cost conductive textile fabric. A Plackett–Burman design of experiment was used to optimize lime peel extract (LPE) mediated reduction for the synthesis of AgNPs. The results of this optimization process revealed silver nitrate concentration to be a significant factor in both size and UV-vis absorption maxima of the LPE-synthesized AgNPs, and reaction temperature also affecting UV-vis absorption maxima. The resultant optimized AgNPs were consistent in size (40–80 nm) and dispersity (PDI = 0.250). The LPE-synthesized AgNPs are used to form a AgNP-Ppy nanocomposite with a linen textile to produce an e-textile with low electrical resistance (37 Ω). GRAPHICAL ABSTRACT
{"title":"Development of conductive textile fabric using Plackett–Burman optimized green synthesized silver nanoparticles and in situ polymerized polypyrrole","authors":"Ashleigh Naysmith, N. S. Mian, S. Rana","doi":"10.1080/17518253.2022.2158690","DOIUrl":"https://doi.org/10.1080/17518253.2022.2158690","url":null,"abstract":"ABSTRACT Electronic textiles (e-textiles) are undergoing rapid technological advancements to attain e-textiles that look and feel like conventional textile fabrics. Research seeks to develop highly functionalized textile-based sensors, actuators, and energy storage devices that integrate seamlessly with current textile technologies. Presently, developments are limited by either low electrical performance, or high cost and complex construction. Additionally, negotiating the balance between high performing e-textiles and environmentally benign production is a challenge. In this report, green synthesized silver nanoparticles (AgNPs) are composited with the conjugated polymer, polypyrrole (Ppy), to create a low-cost conductive textile fabric. A Plackett–Burman design of experiment was used to optimize lime peel extract (LPE) mediated reduction for the synthesis of AgNPs. The results of this optimization process revealed silver nitrate concentration to be a significant factor in both size and UV-vis absorption maxima of the LPE-synthesized AgNPs, and reaction temperature also affecting UV-vis absorption maxima. The resultant optimized AgNPs were consistent in size (40–80 nm) and dispersity (PDI = 0.250). The LPE-synthesized AgNPs are used to form a AgNP-Ppy nanocomposite with a linen textile to produce an e-textile with low electrical resistance (37 Ω). GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"8 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84148078","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 : 2022-12-30DOI: 10.1080/17518253.2022.2154573
Cicely M. Warne, S. Fadlallah, A. Whitwood, James Sherwood, Louis M. M. Mouterde, F. Allais, G. Guebitz, C. McElroy, A. Pellis
ABSTRACT Polyesters are important materials with a wide range of applications, but there has been increasing concern over their sustainability. One example is the need for safer, bio-derived solvents to replace those currently in use for the polymer’s synthesis and processing. In this work, several variants of the bio-based cellulose/levoglucosenone derived solvent Cyrene, namely the ketal derivatives dioxolane Cygnet, dioxane Cygnet and dioxepane Cygnet were synthesized and tested as media for enzymatic polycondensation reactions using bio-based building blocks. Dioxolane Cygnet and dioxepane Cygnet were found to be suitable solvents for enzymatic polycondensation reactions, with dioxolane Cygnet being the preferred solvent, yielding polymers with a Mn >22 kDa. In addition, these solvents were tested in the biocatalyzed synthesis of levoglucosenone-based polyesters. The alternative solvents gave superior yields to those previously observed, demonstrating the versatility of these solvents in enzymatic polycondensation reactions, representing the first synthetic polymer-solvent system fully derived from cellulose. GRAPHICAL ABSTRACT
{"title":"Levoglucosenone-derived synthesis of bio-based solvents and polyesters","authors":"Cicely M. Warne, S. Fadlallah, A. Whitwood, James Sherwood, Louis M. M. Mouterde, F. Allais, G. Guebitz, C. McElroy, A. Pellis","doi":"10.1080/17518253.2022.2154573","DOIUrl":"https://doi.org/10.1080/17518253.2022.2154573","url":null,"abstract":"ABSTRACT Polyesters are important materials with a wide range of applications, but there has been increasing concern over their sustainability. One example is the need for safer, bio-derived solvents to replace those currently in use for the polymer’s synthesis and processing. In this work, several variants of the bio-based cellulose/levoglucosenone derived solvent Cyrene, namely the ketal derivatives dioxolane Cygnet, dioxane Cygnet and dioxepane Cygnet were synthesized and tested as media for enzymatic polycondensation reactions using bio-based building blocks. Dioxolane Cygnet and dioxepane Cygnet were found to be suitable solvents for enzymatic polycondensation reactions, with dioxolane Cygnet being the preferred solvent, yielding polymers with a Mn >22 kDa. In addition, these solvents were tested in the biocatalyzed synthesis of levoglucosenone-based polyesters. The alternative solvents gave superior yields to those previously observed, demonstrating the versatility of these solvents in enzymatic polycondensation reactions, representing the first synthetic polymer-solvent system fully derived from cellulose. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"276 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77058921","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 : 2022-12-29DOI: 10.1080/17518253.2022.2153087
Rachele N. Carafa, D. Foucher, G. Sacripante
ABSTRACT The ongoing threat of global warming has resulted in numerous attempts to reduce greenhouse gas emissions and impede its ramifications. Replacing fossil fuels in products with renewable biobased materials is currently one approach to tackle the climate change crisis. Lignocellulose is the most abundant natural biomass source and is a potential candidate to replace the non-renewable resources currently made with petroleum-based products. Cellulose, hemicellulose, and lignin, which together make up lignocellulose, are all suitable choices for the creation of biobased materials. This review aims to highlight some of the recent efforts towards synthesizing renewable biobased polymers from raw lignocellulose, as well as refined cellulose, hemicellulose, and lignin sources while identifying some of the current applications to which they are suited. GRAPHICAL ABSTRACT
{"title":"Biobased polymers from lignocellulosic sources","authors":"Rachele N. Carafa, D. Foucher, G. Sacripante","doi":"10.1080/17518253.2022.2153087","DOIUrl":"https://doi.org/10.1080/17518253.2022.2153087","url":null,"abstract":"ABSTRACT The ongoing threat of global warming has resulted in numerous attempts to reduce greenhouse gas emissions and impede its ramifications. Replacing fossil fuels in products with renewable biobased materials is currently one approach to tackle the climate change crisis. Lignocellulose is the most abundant natural biomass source and is a potential candidate to replace the non-renewable resources currently made with petroleum-based products. Cellulose, hemicellulose, and lignin, which together make up lignocellulose, are all suitable choices for the creation of biobased materials. This review aims to highlight some of the recent efforts towards synthesizing renewable biobased polymers from raw lignocellulose, as well as refined cellulose, hemicellulose, and lignin sources while identifying some of the current applications to which they are suited. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"115 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88434460","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 : 2022-12-29DOI: 10.1080/17518253.2022.2150394
Aboubakr Haredi Abdelmonsef, A. El-Saghier, A. Kadry
ABSTRACT The overexpression of Rab proteins was linked to cancer development, making this family of proteins an attractive drug target for the identification of novel inhibitors against tumor diseases. In this study, novel triazole-based azomethine/thiazolidin-4-one hybrid analogs were designed, prepared and structurally confirmed by using elemental and spectral techniques, these include FT-IR, MS, and NMR spectra. In addition, in vitro cytotoxic activity was assessed against NCI-60 cancer cell lines. To understand the possible mode of action and drugability, molecular docking studies and drug-likeness were achieved. The docking simulations were performed against various Rab family proteins Rab2a, Rab25, Rab5, and Rab35; promising targets for cancer medication to support the cytotoxicity findings and to further validate the action of new molecules. Furthermore, in silico ADMET screening of the molecules was within the recommended values stated by Lipinski's rule of five (Ro5), indicating their oral bioavailability and therapeutic potentials. Among the newly prepared analogs tested, compounds 4d and 3d exhibited significant antitumor activity against breast, ovarian, lung, and leukemia cancer cell lines. Our findings suggested that azomethine/thiazolidin-4-one moieties incorporated triazole analogs are a promising class of molecular entities for the development of new anticancer therapies, through targeting of some Rab proteins. GRAPHICAL ABSTRACT
{"title":"Ultrasound-assisted green synthesis of triazole-based azomethine/thiazolidin-4-one hybrid inhibitors for cancer therapy through targeting dysregulation signatures of some Rab proteins","authors":"Aboubakr Haredi Abdelmonsef, A. El-Saghier, A. Kadry","doi":"10.1080/17518253.2022.2150394","DOIUrl":"https://doi.org/10.1080/17518253.2022.2150394","url":null,"abstract":"ABSTRACT The overexpression of Rab proteins was linked to cancer development, making this family of proteins an attractive drug target for the identification of novel inhibitors against tumor diseases. In this study, novel triazole-based azomethine/thiazolidin-4-one hybrid analogs were designed, prepared and structurally confirmed by using elemental and spectral techniques, these include FT-IR, MS, and NMR spectra. In addition, in vitro cytotoxic activity was assessed against NCI-60 cancer cell lines. To understand the possible mode of action and drugability, molecular docking studies and drug-likeness were achieved. The docking simulations were performed against various Rab family proteins Rab2a, Rab25, Rab5, and Rab35; promising targets for cancer medication to support the cytotoxicity findings and to further validate the action of new molecules. Furthermore, in silico ADMET screening of the molecules was within the recommended values stated by Lipinski's rule of five (Ro5), indicating their oral bioavailability and therapeutic potentials. Among the newly prepared analogs tested, compounds 4d and 3d exhibited significant antitumor activity against breast, ovarian, lung, and leukemia cancer cell lines. Our findings suggested that azomethine/thiazolidin-4-one moieties incorporated triazole analogs are a promising class of molecular entities for the development of new anticancer therapies, through targeting of some Rab proteins. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"67 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73746383","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 : 2022-12-29DOI: 10.1080/17518253.2022.2134740
Xiaolong Ma, Jinfeng Wei, Xu Yang, Hua-Jin Xu, Yiyong Hu
ABSTRACT Direct C–H bond functionalization is the most effective technique to construct C–X (X = C, N, O, S, etc.), which could simplify the conventional synthesis methods. Transition-metal-catalyzed C–H bond functionalization needs metal catalysts such as palladium, rhodium, iridium, cobalt, copper, etc., which is not conducive to its sustainable development. In recent years, C(sp3)-H bond functionalization without transition metal catalyst has been studied increasingly. In the meantime, electrochemistry has become one of the most dynamic research fields in organic synthesis for the reason that it can substitute the traditional expensive and polluting metal salt oxidants (e.g. Cu2+, Ag+ salt) with current/electrons to act as a redox agent. So the applications of electrochemistry combined with transition-metal-free C(sp3)-H bond functionalization to solve some long-standing challenges have gradually gotten more and more attention in recent years. In this review, the researches on transition-metal-free electrochemical-induced C(sp3)-H bond functionalization from 2016 to now will be systematically presented and the future research hotspots and difficulties in this field will also be prospected. GRAPHICAL ABSTRACT
{"title":"Transition-metal-free electrochemical-induced active C(sp3)-H functionalization","authors":"Xiaolong Ma, Jinfeng Wei, Xu Yang, Hua-Jin Xu, Yiyong Hu","doi":"10.1080/17518253.2022.2134740","DOIUrl":"https://doi.org/10.1080/17518253.2022.2134740","url":null,"abstract":"ABSTRACT Direct C–H bond functionalization is the most effective technique to construct C–X (X = C, N, O, S, etc.), which could simplify the conventional synthesis methods. Transition-metal-catalyzed C–H bond functionalization needs metal catalysts such as palladium, rhodium, iridium, cobalt, copper, etc., which is not conducive to its sustainable development. In recent years, C(sp3)-H bond functionalization without transition metal catalyst has been studied increasingly. In the meantime, electrochemistry has become one of the most dynamic research fields in organic synthesis for the reason that it can substitute the traditional expensive and polluting metal salt oxidants (e.g. Cu2+, Ag+ salt) with current/electrons to act as a redox agent. So the applications of electrochemistry combined with transition-metal-free C(sp3)-H bond functionalization to solve some long-standing challenges have gradually gotten more and more attention in recent years. In this review, the researches on transition-metal-free electrochemical-induced C(sp3)-H bond functionalization from 2016 to now will be systematically presented and the future research hotspots and difficulties in this field will also be prospected. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"406 2","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72457636","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 : 2022-12-22DOI: 10.1080/17518253.2022.2151323
Sadeq M. Al-Hazmy, D. Bensalah, N. A. Dlala, Younes Bouazizi, H. Ghalla, N. Hamdi
ABSTRACT New Dicoumarols 2a-g efficiently synthesized employing p-TSA as a catalyst from the reaction of 4-hydroxycoumarin with aryl aldehydes in water. This method offers direct access to structurally diverse Dicoumarols derivatives in a good yields (65-94%). Upon heating 3,3' -arylidenebis-4-hydroxycoumarins derivative in acetic anhydride, the epoxydicoumarins were formed. 1H, 13C{1H}-NMR, elemental analysis, and infrared spectroscopic techniques were used for the characterization of the obtained compounds. A possible relationship between such hydrogen-bonded structures and the antimicrobial and the antioxidant activities of compounds is suggested. The synthetized compounds 2a-g and 3a-g were subjected to in vitro antimicrobial and antifungal activities against DNA gyrase and Mycobacterium tuberculosis-CYP51 target proteins at the active sites. Compound 3d shows effective inhibitory effect in terms of MIC = 15 µg mL-1. against Salmonella typhimuriumATCC 14028. Compounds 2b, 2c, 3b, 3c, 3e and 3g have recorded an important scavenging activity against the radical DPPH. The EC50 of these compounds was 47.17, 46.90, 50.55,48.27 , 46.55 and 47.54 µg mL-1 respectively. Investigation of the anti-inflammatory activity of the synthesized compounds showed that compounds 2b,2c, 3f, 3b and 3c are the most potent inflammatory activities. GRAPHICAL ABSTRACT
{"title":"A facile and practical p-toluenesulfonic acid catalyzed route to dicoumarols and their biological evaluation","authors":"Sadeq M. Al-Hazmy, D. Bensalah, N. A. Dlala, Younes Bouazizi, H. Ghalla, N. Hamdi","doi":"10.1080/17518253.2022.2151323","DOIUrl":"https://doi.org/10.1080/17518253.2022.2151323","url":null,"abstract":"ABSTRACT New Dicoumarols 2a-g efficiently synthesized employing p-TSA as a catalyst from the reaction of 4-hydroxycoumarin with aryl aldehydes in water. This method offers direct access to structurally diverse Dicoumarols derivatives in a good yields (65-94%). Upon heating 3,3' -arylidenebis-4-hydroxycoumarins derivative in acetic anhydride, the epoxydicoumarins were formed. 1H, 13C{1H}-NMR, elemental analysis, and infrared spectroscopic techniques were used for the characterization of the obtained compounds. A possible relationship between such hydrogen-bonded structures and the antimicrobial and the antioxidant activities of compounds is suggested. The synthetized compounds 2a-g and 3a-g were subjected to in vitro antimicrobial and antifungal activities against DNA gyrase and Mycobacterium tuberculosis-CYP51 target proteins at the active sites. Compound 3d shows effective inhibitory effect in terms of MIC = 15 µg mL-1. against Salmonella typhimuriumATCC 14028. Compounds 2b, 2c, 3b, 3c, 3e and 3g have recorded an important scavenging activity against the radical DPPH. The EC50 of these compounds was 47.17, 46.90, 50.55,48.27 , 46.55 and 47.54 µg mL-1 respectively. Investigation of the anti-inflammatory activity of the synthesized compounds showed that compounds 2b,2c, 3f, 3b and 3c are the most potent inflammatory activities. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"18 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84817982","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 : 2022-12-22DOI: 10.1080/17518253.2022.2147027
Lifang Wang, Xinhai Zhu, Zexuan Liang, Manna Huang, Y. Wan
ABSTRACT An effective ligand for the Ullmann-type C–N coupling reaction in water has been obtained using a novel tactic, namely, introducing a third group into the ligand to both improve the ligand’s water solubility and enhance the ligand’s coordinating ability. Applying this method, we have developed an effective ligand for the Cu-catalyzed amination of aryl halides, in particular, for aryl chlorides in water. The substrate diversity of the catalyst system, relatively less time required (6–12 h), and water as the reaction solvent make it attractive in both academia and industry. GRAPHICAL ABSTRACT
{"title":"Design and application of a novel and effective ligand for the Cu-catalyzed amination of aryl halides in water","authors":"Lifang Wang, Xinhai Zhu, Zexuan Liang, Manna Huang, Y. Wan","doi":"10.1080/17518253.2022.2147027","DOIUrl":"https://doi.org/10.1080/17518253.2022.2147027","url":null,"abstract":"ABSTRACT An effective ligand for the Ullmann-type C–N coupling reaction in water has been obtained using a novel tactic, namely, introducing a third group into the ligand to both improve the ligand’s water solubility and enhance the ligand’s coordinating ability. Applying this method, we have developed an effective ligand for the Cu-catalyzed amination of aryl halides, in particular, for aryl chlorides in water. The substrate diversity of the catalyst system, relatively less time required (6–12 h), and water as the reaction solvent make it attractive in both academia and industry. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"1 1","pages":""},"PeriodicalIF":6.6,"publicationDate":"2022-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79686688","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 : 2022-10-02DOI: 10.1080/17518253.2022.2129464
C. Blázquez-Barbadillo, Juan F González, A. Porcheddu, D. Virieux, J. Menéndez, E. Colacino
ABSTRACT The solvent-free preparation of unsymmetrical N-aryl-5,6-unsubstituted-1,4-dihydropyridines (DHPs) by ball-milling was investigated. Three different mechanochemical domino reactions (one-pot/one step or stepwise) were studied, the process parameters underlying any mechanochemical process were modulated and the differences with solution-based mechanistic pathways were disclosed. The selection of the most suitable method was driven by the physical state of both the reactants and the intermediates, while the physical state of the final 1,4-DHP directed the choice of the catalyst (Lewis vs Brønsted) and the type of work-up to recover the final products (by column chromatography vs precipitation in water). The results herein described are unprecedented in the arena of synthetic methods to access diversely substituted 1,4-DHPs, an N-heterocyclic scaffold relevant to both synthetic and medicinal purposes. GRAPHICAL ABSTRACT
研究了球磨法制备不对称n -芳基-5,6-未取代-1,4-二氢吡啶(DHPs)的方法。研究了三种不同的机械化学多米诺骨牌反应(一锅/一步或逐步)，对任何机械化学过程的工艺参数进行了调节，并揭示了与基于溶液的机械化学途径的差异。选择最合适的方法是由反应物和中间体的物理状态驱动的，而最终的1,4- dhp的物理状态指导催化剂的选择(Lewis vs Brønsted)和回收最终产物的后处理类型(柱层析vs水中沉淀)。本文所描述的结果在合成方法领域是前所未有的，以获得不同取代的1,4- dhps，这是一种与合成和药用用途相关的n -杂环支架。图形抽象
{"title":"Benign synthesis of therapeutic agents: domino synthesis of unsymmetrical 1,4-diaryl-1,4-dihydropyridines in the ball-mill","authors":"C. Blázquez-Barbadillo, Juan F González, A. Porcheddu, D. Virieux, J. Menéndez, E. Colacino","doi":"10.1080/17518253.2022.2129464","DOIUrl":"https://doi.org/10.1080/17518253.2022.2129464","url":null,"abstract":"ABSTRACT The solvent-free preparation of unsymmetrical N-aryl-5,6-unsubstituted-1,4-dihydropyridines (DHPs) by ball-milling was investigated. Three different mechanochemical domino reactions (one-pot/one step or stepwise) were studied, the process parameters underlying any mechanochemical process were modulated and the differences with solution-based mechanistic pathways were disclosed. The selection of the most suitable method was driven by the physical state of both the reactants and the intermediates, while the physical state of the final 1,4-DHP directed the choice of the catalyst (Lewis vs Brønsted) and the type of work-up to recover the final products (by column chromatography vs precipitation in water). The results herein described are unprecedented in the arena of synthetic methods to access diversely substituted 1,4-DHPs, an N-heterocyclic scaffold relevant to both synthetic and medicinal purposes. GRAPHICAL ABSTRACT","PeriodicalId":12768,"journal":{"name":"Green Chemistry Letters and Reviews","volume":"43 1","pages":"881 - 892"},"PeriodicalIF":6.6,"publicationDate":"2022-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76408189","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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