Article
Chemistry, Medicinal
Petra R. Varga, Rita Olahne Szabo, Gyorgy Dorman, Szilvia Bosze, Gyorgy Keglevich
Summary: Motivated by the cytotoxicity of a-aminophosphonates, a library of various derivatives was established and evaluated on tumor cells of different tissue origins. Some derivatives showed selective cytostatic effects, with phosphinoylmethyl-aminophosphonate derivative 2e exhibiting significant activity against breast and prostate cancer cells. These new compounds hold promise as alternative chemotherapeutic agents against different tumor types.
Article
Chemistry, Organic
Shogo Nakamura, Soshi Nishino, Koji Hirano
Summary: A copper-catalyzed regioselective hydroamination method was developed to synthesize alpha-aminophosphonates from alpha,beta-unsaturated phosphonates, which are of interest in medicinal chemistry. The use of an umpolung, electrophilic amination strategy with a hydroxylamine derivative is key to achieving the desired regioselectivity, as compared to the conventional nucleophilic hydroamination conditions with the parent amine. The article also discusses the asymmetric synthesis using a chiral bisphosphine ligand and its application in a related silylamination reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yijing Dai, Li Zheng, Debarshi Chakraborty, Babak Borhan, William D. Wulff
Summary: An effective catalyst has been developed for the three-component reaction of aldehydes, anilines and phosphites in an asymmetric catalytic Kabachnik-Fields reaction to give alpha-aminophosphonates. The optimal catalyst is prepared from specific ligands and zirconium tetraisopropoxide, and in the presence of benzoic acid. The best conditions for aryl aldehydes and aliphatic aldehydes were identified, with comparable asymmetric inductions achieved for both types of aldehydes.
Article
Chemistry, Multidisciplinary
Vipin K. Pandey, Chandra Shekhar Tiwari, Arnab Rit
Summary: A silver salt-catalyzed aminophosphonylation and Strecker reaction were developed, and mechanistic studies revealed a radical pathway. This reaction system can effectively operate at room temperature without the need for solvents, ligands, or bases, and it can produce diverse products.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Yan-Long Zheng, Pei-Pei Xie, Omid Daneshfar, Kendall N. Houk, Xin Hong, Stephen G. Newman
Summary: A new method has been developed to convert alkyl esters into alkyl ketones, resulting in the synthesis of 65 different alkyl ketones with various functional groups and heterocyclic structures. The study found that catalyst-controlled chemoselectivity could activate the C(acyl)-O bond in the substrate, while density functional theory calculations supported the mechanism of the nickel catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xianyuan Wu, Mario De Bruyn, Katalin Barta
Summary: Primary amines are important for the synthesis of various industrial products. A comprehensive catalytic strategy allows for the direct sourcing of diverse primary amines from lignocellulosic biomass with minimal purification effort. The core of the methodology is the efficient RANEY (R) Ni-catalyzed hydrogen-borrowing amination of alcohol intermediates.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Food Science & Technology
Wei Xia, Yifan Wang, Ran Bi, Jing Wu
Summary: This study aimed to investigate the transglycosylation property of the GH31 alpha-glucosidase from Thermoplasma acidophilum and evaluate its application performance in the preparation of Nigerooligosaccharides (NOS). The results showed that the enzyme exhibited selectivity for different linkages during hydrolysis and transglycosylation. Using glucose and maltose as substrates, the enzyme yielded high levels of NOS with good purity. These findings provide a new candidate for large-scale enzymatic synthesis of NOS and have important theoretical significance for the study of GH31 alpha-glucosidase.
Article
Chemistry, Organic
Jiawei Guo, Song Liu, Qinjiao Pang, Hongyun Zhang, Lu Gao, Li Chen, Zhenlei Song
Summary: An efficient synthesis of silacyclohexanones with different silyl substituents has been developed using a [Rh(coe)(2)Cl](2)/PCy3 catalyst, which can be further oxidized to form silacyclohexadienones and transformed into silicon analogs of 2-deoxystreptamine or exo-alkylidenesilacyclohexadienes.
Article
Chemistry, Multidisciplinary
Jianwang Xu, Xinge Miao, Lei Liu, Yantao Wang, Weiran Yang
Summary: A robust catalytic system has been developed for the green synthesis of 5-methylfurfural using iodide-mediated transfer hydrogenation. The system allows for efficient synthesis of 5-MF from d-fructose and can be used for six consecutive cycles without any decrease in yield. Additionally, the co-production of 5-MF and furfural from raw biomass makes this methodology more competitive than other routes.
Article
Biochemistry & Molecular Biology
Ichrak Souii, Med Abderrahmane Sanhoury, Javier Vicario, Xabier Jimenez-Aberasturi, Mohamed L. Efrit, Hedi M'rabet, Jesus M. de los Santos
Summary: In this study, several bis(a-aminophosphonates) were efficiently prepared using a catalyst-free multicomponent Kabachnik-Fields reaction, achieving high yields. Furthermore, the nucleophilic substitution reaction between the synthesized bis(a-aminophosphonates) and ethyl (2-bromomethyl)acrylate under mild conditions led to a novel synthetic approach to a new series of bis(allylic-a-aminophosphonates).
Article
Chemistry, Physical
Dominik Koszelewski, Pawel Kowalczyk, Pawel Smigielski, Jan Samsonowicz-Gorski, Karol Kramkowski, Aleksandra Wypych, Mateusz Szymczak, Ryszard Ostaszewski
Summary: We reported a novel method for the synthesis of pharmacologically relevant alpha-aminophosphonate derivatives via a lipase-catalyzed Kabachnik-Fields reaction, achieving yields of up to 93%. This method offers advantages such as high yields, mild reaction conditions, low costs, and sustainability. Additionally, a new class of alpha-aminophosphonate analogues with P-chiral centers was synthesized. The presence of different alkoxy groups on antimicrobial activity was demonstrated, highlighting the importance of substituents on the aromatic rings.
Article
Biochemistry & Molecular Biology
Zhong-Lei Meng, Ru-Si Wen, Xiao-Rui Huang, Rong-Xiu Qin, Yi-Ming Hu, Yong-Hong Zhou
Summary: This study utilizes five alpha-hydroxy acids as catalysts for synthesizing terpineol from alpha-pinene. The use of ternary composite catalysts showed significant improvement in the catalytic performance. The optimal reaction conditions were identified, and the conversion of alpha-pinene, content and selectivity of alpha-terpineol were measured. Furthermore, the study also examined the catalytic performance of monolayer graphene oxide and its composite catalyst with citric acid.
Article
Chemistry, Multidisciplinary
Foad Kazemi, Yadollah Shariati, Babak Kaboudin
Summary: This paper reports a simple, metal-free, and homogeneous two-step one-pot method for the synthesis of α-aminophosphonate using alcohol as a starting material and tetrabutylammonium tribromide (TBATB) as a catalyst. The reaction shows efficient catalytic effects for both photo tunable aerobic oxidation of alcohol and synthesis of α-aminophosphonate from in situ prepared aldehyde.
Review
Biochemistry & Molecular Biology
Aitor Maestro, Xabier del Corte, Adrian Lopez-Frances, Edorta Martinez de Marigorta, Francisco Palacios, Javier Vicario
Summary: Alpha-aminophosphonic acid derivatives are biologically active molecules due to their structural similarity to natural alpha-amino acids. The synthesis of alpha-aminophosphonates with tetrasubstituted carbons in an asymmetric manner has gained interest in recent decades, given the importance of tetrasubstituted carbons in nature and medicine and the biological activity dependence on absolute configuration of chiral molecules. Existing literature on the synthesis of optically active tetrasubstituted alpha-aminophosphonates, involving diastereoselective and enantioselective approaches, is summarized.
Article
Chemistry, Applied
Swetha Jos, Webster L. Santos
Summary: The synthesis of alpha-trifluoromethylacrylates from alpha-trifluoroborylacrylates via stereoretentive radical trifluoromethylation at room temperature using inexpensive reagents NaSO(2)CF(3) and TBHP resulted in the exclusive formation of the (E)-diastereomer in moderate to good yield. The reaction products were demonstrated to be useful in the synthesis of phenyl-4H-pyran, a potent and selective class of IKCa channel blockers.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Pharmacology & Pharmacy
Epolc N. Ntungwe, Eva M. Dominguez-Martin, Amilcar Roberto, Joana Tavares, Vera M. S. Isca, Paula Pereira, Maria-Joao Cebola, Patricia Rijo
CURRENT PHARMACEUTICAL DESIGN
(2020)
Article
Biochemistry & Molecular Biology
Vera M. S. Isca, Milan Sencanski, Nenad Filipovic, Daniel J. V. A. Dos Santos, Ana Cipak Gasparovic, Lucilia Saraiva, Carlos A. M. Afonso, Patricia Rijo, Alfonso T. Garcia-Sosa
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Medicinal
Vera M. S. Isca, Ricardo J. Ferreira, Catarina Garcia, Carlos M. Monteiro, Jelena Dinic, Suvi Holmstedt, Vania Andre, Milica Pesic, Daniel J. V. A. dos Santos, Nuno R. Candeias, Carlos A. M. Afonso, Patricia Rijo
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Medicinal
Tomasz Sliwinski, Przemyslaw Sitarek, Ewa Skala, Vera M. S. Isca, Ewelina Synowiec, Tomasz Kowalczyk, Michal Bijak, Patricia Rijo
Article
Chemistry, Multidisciplinary
Ana C. Fernandes
Summary: The study focuses on the reductive depolymerization of plastic waste into value-added compounds using a zinc catalyst, which shows good yields and effectiveness. The catalytic system is also able to selectively depolymerize plastic mixtures, and the catalyst can be reused for multiple cycles with good yields.
Article
Cell Biology
Tomasz Kowalczyk, Anna Merecz-Sadowska, Patricia Rijo, Vera M. S. Isca, Laurent Picot, Marzena Wielanek, Tomasz Sliwinski, Przemyslaw Sitarek
Summary: This study is the first to establish transformed root cultures of Leonotis nepetifolia, and reveals differences in compound content between transformed and nontransformed roots. Biological studies show that LNTR4 root extract exhibits cytotoxic effects on multiple cancer cell lines, indicating its potential as an effective and affordable source of bioactive secondary metabolites for further exploration.
Article
Chemistry, Medicinal
Rafael F. A. Gomes, Vera M. S. Isca, Kessia Andrade, Patricia Rijo, Carlos A. M. Afonso
Summary: Naturally occurring cyclopentenones, such as palmenones and nigrosporiones, show antimicrobial activity, and derivatives accessible from biomass derivatives furfural and 5-hydroxymethylfurfural were found to exhibit significant antimicrobial activity against Gram-positive bacteria, including resistant strains like MRSA and VRE.
Article
Biochemistry & Molecular Biology
Nuray Erin, Esra Tavsan, Ozlem Akdeniz, Vera M. S. Isca, Patricia Rijo
Summary: Activation of CXCR2 by chemokines promotes breast cancer aggressiveness and chemoresistance, but CXCR2 antagonists are being tested in clinical trials. Inhibition of CXCR2 may lead to increased secretion of MIP-2 and KC, which can be prevented by PKC activators. Different PKC activators have varying effects on chemokine secretion and cell proliferation, with PKC delta and PKC epsilon activators showing the most effectiveness in preventing chemoresistance.
Article
Chemistry, Physical
Daniel L. Lourenco, Ana C. Fernandes
Summary: The sustainable synthesis of pharmaceuticals from plastic waste presents an innovative and eco-friendly approach for the pharmaceutical industry. This study reports the use of catalyst systems for the reductive depolymerization of plastic waste, as well as the development of a synthetic strategy for the production of an anticancer drug from plastic waste.
Article
Biochemistry & Molecular Biology
Claudia Bessa, Joana B. Loureiro, Matilde Barros, Vera M. S. Isca, Vilma A. Sardao, Paulo J. Oliveira, Raquel L. Bernardino, Carina Herman-de-Sousa, Maria Adelina Costa, Paulo Correia-de-Sa, Marco G. Alves, Patricia Rijo, Lucilia Saraiva
Summary: This study identified a compound called Roy-Bz, which activates PKC delta and inhibits both mitochondrial respiration and glycolysis in colon cancer cells. These findings suggest a potential dual role of PKC delta in tumor cell metabolism and highlight the therapeutic potential of Roy-Bz in targeting glucose metabolism.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Physical
Daniel L. Lourenco, Ana C. Fernandes
Summary: In this work, we present an efficient protocol for reducing esters and lactones, as well as depolymerizing various polyester plastic waste using the catalytic system HBpin/MoO2Cl2(H2O)2. The reactions occur under mild conditions and exhibit excellent yields. The inexpensive and environmentally friendly MoO2Cl2(H2O)2 catalyst is capable of catalyzing at least 8 consecutive reductions of PCL with good yields.
MOLECULAR CATALYSIS
(2023)
Article
Green & Sustainable Science & Technology
Daniel L. Lourenco, Daniela F. Oliveira, Ana C. Fernandes
Summary: This work presents the depolymerization of polyester and polycarbonate plastic waste into valuable compounds using manganese compounds as catalysts and boranes and silanes as reducing agents. The results showed good to excellent yields, and a commercially available manganese catalyst called Si-Mn was proven to be highly efficient. The study also investigated the consecutive depolymerization of polyesters using different manganese catalysts, which showed excellent catalytic activity.
ADVANCED SUSTAINABLE SYSTEMS
(2023)
Article
Green & Sustainable Science & Technology
Tamara A. H. Branco, Ana C. Fernandes
Summary: This work presents a new method for efficiently breaking down polyester and polycarbonate plastic waste using pinacolborane (HBpin) catalyzed by Zn(OAc)2.2H2O and Zn(OTf)2. The method combines non-toxic, inexpensive zinc catalysts with a mild reducing agent, resulting in excellent yields under mild reaction conditions.
ADVANCED SUSTAINABLE SYSTEMS
(2023)
Review
Chemistry, Multidisciplinary
Ana C. Fernandes
Summary: Recent studies have shown that reductive depolymerization is an excellent method for converting plastic waste into value-added products, thus addressing the negative impact of plastic on the environment and human health. Catalysts play a crucial role in this process.
Article
Chemistry, Multidisciplinary
Beatriz F. S. Nunes, M. Conceicao Oliveira, Ana C. Fernandes
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
