Article
Biochemistry & Molecular Biology
Yueteng Zhang, Peng Ji, Xiang Meng, Feng Gao, Fanxun Zeng, Wei Wang
Summary: A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes, which involved the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.
Article
Chemistry, Organic
Meng-Hao Yi, Hai-Shan Jin, Ru-Bing Wang, Li-Ming Zhao
Summary: An efficient copper-catalyzed cascade annulation of o-hydroxyphenyl propargylamines and pyrazolin-5-ones is described, leading to the rapid assembly of a series of valuable pyrano[2,3-c]pyrazoles with good yields across a wide range of substrates in a simple fashion. The mechanistic elucidation is well supported by control experiment and literature precedents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Huaibin Yu, Shuangshuang Wang, Jianjian Huang, Yu Fu, Manfred Wagner, Tanja Weil, Fangrui Zhong, Weining Zhao, Yuzhou Wu
Summary: This article reports the molecular design of a novel multifunctional reagent for light-controlled selective protein labeling. The molecule combines the functionalities of protein-ligand recognition, bioconjugation, ligand cleavage, and photoactivation. By releasing a highly electrophilic o-naphthoquinone methide, the reagent achieves proximity-driven selective labeling with the protein of interest while retaining its native function.
Article
Biochemistry & Molecular Biology
Shosuke Ito, Hitomi Tanaka, Makoto Ojika, Kazumasa Wakamatsu, Manickam Sugumaran
Summary: DOPAL, formed by the oxidation of dopamine, is a toxic metabolite associated with neurogenerative diseases such as Parkinson's. Its oxidation product, DOPAL-quinone, generates various toxic compounds that contribute to its neurotoxicity.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Guangming Nan, Jingbo Zhan, Chunming Yuan, Lirong Wen, Ming Li
Summary: This novel method involves the synthesis of highly substituted 4H-chromene derivatives through NEt3-promoted annulation of beta-ketothioamides and ortho-quinone methides. The method exhibits good functional group tolerance, simple operation, and scalability.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Waldemar Iwanek
Summary: This paper describes the reaction pathways and activation energies of alkoxybenzyl derivatives of resorcin[4]arene leading to the formation of o-quinomethide derivatives of resorcin[4]arene. The reaction mechanisms of o-QMR[4]A formation were proposed based on the calculated pathways. The energies of reactants, transition states, and products were calculated using different density-functional theory methods, and the theoretical reaction mechanisms were discussed in relation to experimental data.
ROYAL SOCIETY OPEN SCIENCE
(2022)
Review
Chemistry, Multidisciplinary
Zaozao Qiu, Zuowei Xie
Summary: Carborynes, three-dimensional analogues of benzyne, can be generated in situ from specific precursors. They are useful for synthesizing various functionalized carborane derivatives and exhibit unique properties. Carborynes exhibit pericyclic reaction modes similar to benzyne, but also have their own distinctive features. Previous research has explored the unique reaction modes and mechanisms of carborynes.
CHEMICAL SOCIETY REVIEWS
(2022)
Review
Chemistry, Multidisciplinary
Maria Tereza M. Martins, Flaviana Rodrigues F. Dias, Raphael Silva M. de Moraes, Marcos Felipe da Silva, Kaio R. Lucio, Karin D'Oliveira Goes, Patrick A. do Nascimento, Andre S. S. da Silva, Vitor F. Ferreira, Anna C. Cunha
Summary: This article provides an overview of multicomponent reactions (MCRs) that involve ortho-quinone methide intermediates (o-QM) and discusses their applications in organic synthesis and biological processes. QMs are generated through eliminative processes or photochemical reactions and can undergo various types of reactions.
Article
Chemistry, Organic
Diksha Rajput, Gowsia Jan, Muthu Karuppasamy, Nattamai Bhuvanesh, Subbiah Nagarajan, C. Uma Maheswari, J. Carlos Menendez, Vellaisamy Sridharan
Summary: An efficient cascade annulation reaction using secondary amine catalyst was developed for the synthesis of functionalized 2H-chromenes and 1,2-dihydroquinolines with a p-quinone methide scaffold. The microwave-assisted strategy achieved high yields and completion of reactions in just 15 min. The synthesized products were further transformed into valuable compounds via a palladium-catalyzed double C-H bond activation process and epoxidation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Mingyu Zhang, Yaodong Hu, Wei Li, Chen Sun, Chunjing Guan, Ying Peng, Jiang Zheng
Summary: 2,6-Dimethylphenol (2,6-DMP) is an environmental pollutant that can be metabolized into a reactive compound, leading to liver toxicity. This study found that the reactive metabolite of 2,6-DMP can react with certain molecules in the liver, resulting in the formation of protein adducts. The liver toxicity and protein adduct formation were dependent on the dose of 2,6-DMP.
CHEMICAL RESEARCH IN TOXICOLOGY
(2022)
Article
Chemistry, Organic
Kohsuke Kato, Daisuke Uraguchi, Takashi Ooi
Summary: A new o-QM catalyst was developed for the dehydridative oxidation of benzylic alcohols. The introduction of an overcrowded olefinic component into o-QM induced structural distortion, beneficial for imparting triarylmethylium character and regenerability. The zwitterionic resonance form of o-QM generated through photoexcitation and relaxation exhibited dehydridation activity.
Article
Chemistry, Applied
Santosh J. Gharpure, Santosh K. Nanda, Dipak J. Fartade
Summary: This study demonstrates a facile synthesis of 1,4-heterocycle-fused quinoline motifs through intramolecular formal [4+2]-cycloaddition, involving tandem bond formation reactions and showing excellent functional group tolerance, leading to the synthesis of enantiomerically enriched compounds. Additionally, sulfoxide embedded quinolines were successfully transformed into pentacyclic 1,4-thiepino tethered indeno-quinoline scaffolds via Pummerer cyclization.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Min Yang, Huiqi Han, Hui Jiang, Shengqing Ye, Xiaona Fan, Jie Wu
Summary: A photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide, and para-quinone methides under visible light irradiation at room temperature is developed to give diarylmethyl alkylsulfones in moderate to good yields. The transformation is initiated by alkyl radicals generated in situ from potassium alkyltrifluoroborates, and subsequent steps involve the insertion of sulfur dioxide and radical 1,6-addition of para-quinone methides with alkylsulfonyl radical intermediates.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Xiaodong Gu, Ling Meng, Mingliang Li, Jun (Joelle) Wang
Summary: A Cu(I)/(R,R)-Ph-BPE-catalyzed enantioselective hydroamination of 2H-chromenes and 2H-thiochromenes with anthranils has been developed, allowing for efficient and atom-economical asymmetric access to a series of 4-arylamino chromanes and thiochromanes with high yields (up to 96%) and excellent enantioselectivities (up to 99% ee). These valuable chiral chromane and thiochromane products serve as key intermediates for accessing nitrogen-, oxygen- and sulfur-containing bioactive compounds with increased molecular complexity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Yvette M. C. A. Luijkx, Anniek J. Henselijn, Gerlof P. Bosman, Dario A. T. Cramer, Koen C. A. P. Giesbers, Esther M. van't Veld, Geert-Jan Boons, Albert J. R. Heck, Karli R. Reiding, Karin Strijbis, Tom Wennekes
Summary: Fucosidases are important in various pathological conditions and the health of the human gut. A new probe has been developed that can selectively label bacterial fucosidases and detect extracellular enzyme activity on live bacteria surfaces.
Article
Biochemistry & Molecular Biology
Amanda A. Borges, Michele P. de Souza, Anna Carolina C. da Fonseca, Guilherme F. Wermelinger, Ruan C. B. Ribeiro, Adriane A. P. Amaral, Claudio Jose C. de Carvalho, Lucas S. Abreu, Lucas Nicolau de Queiroz, Elan C. P. de Almeida, Vitor W. Rabelo, Paula A. Abreu, Bruno Pontes, Vitor F. Ferreira, Fernando de C. da Silva, Luana da S. M. Forezi, Bruno K. Robbs
Summary: This study synthesized 16 chemoselectively derivated Mannich adducts of 1,4-naphthoquinones through a multiple component reaction. These new compounds exhibited good antitumor activity in oral squamous cell carcinoma models with higher selectivity and fewer side effects compared to other chemotherapy drugs. This finding provides important references and guidance for the development of new anticancer candidates.
Editorial Material
Chemistry, Medicinal
Vitor Francisco Ferreira, Fernando de Carvalho da Silva, Luana da Silva Magalhaes Forezi
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Medicinal
Luana da S. M. Forezi, Patricia G. Ferreira, Alcione Silva de Carvalho, Fernando de C. da Silva, Vitor F. Ferreira
Summary: Pharmaceutical chemistry needs to adapt to a new reality where environmental focus is crucial. New technologies that use cleaner and renewable raw materials are needed to reduce harm to the environment. This is especially important in the pharmaceutical industry, as chemical products are used in medicine production and everyday life, and are part of the United Nations' Sustainable Development Goals.
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Juliana Figueiredo Peixoto, Luiz Filipe Goncalves-Oliveira, Franklin Souza-Silva, Luzia Monteiro de Castro Cortes, Geovane Dias-Lopes, Flavia de Oliveira Cardoso, Rafael de Oliveira Santos, Beatriz Ferreira de Carvalho Patricio, Caroline Deckmann Nicoletti, Carolina Guimaraes de Souza Lima, Katia da Silva Calabrese, Davyson de Lima Moreira, Helvecio Vinicius Antunes Rocha, Fernando de Carvalho da Silva, Vitor Francisco Ferreira, Carlos Roberto Alves
Summary: Oil-in-water microemulsions loaded with epoxy-alpha-lapachone (ELAP-ME) were successfully developed and showed good stability. ELAP-ME demonstrated promising activity against murine infection with Leishmania (Leishmania) amazonensis.
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2023)
Article
Polymer Science
Fernanda Petzold Pauli, Cyntia Silva Freitas, Patricia Ribeiro Pereira, Alvicler Magalhaes, Fernando de Carvalho da Silva, Vania M. F. Paschoalin, Vitor Francisco Ferreira
Summary: In this study, chemically-modified chitosan (CS), namely 1,4-NQ-CS and 1,2-NQ-CS, were synthesized using 2,3-dichloro-1,4-naphthoquinone and the sodium salt of 1,2-naphthoquinone-4-sulfonic acid. The synthesized compounds exhibited excellent antimicrobial activities and cytotoxicity, making them suitable for safe application to human tissue. However, caution should be exercised due to the cytotoxicity of 1,4-NQ-CS against breast cancer cells.
Article
Food Science & Technology
Lucileno Rodrigues da Trindade, Diego dos Santos Baiao, Davi Vieira Teixeira da Silva, Cristine Couto Almeida, Fernanda Petzold Pauli, Vitor Francisco Ferreira, Carlos Adam Conte-Junior, Vania Margaret Flosi Paschoalin
Summary: By using different encapsulating agents such as starch and maltodextrin, ready-to-eat beetroot soup can be lyophilized to retain its rich antioxidant compounds and dietary nitrate. Microencapsulated beetroot soup complied with microbiological quality guidelines for consumption and showed good acceptance and purchase intention throughout 90 days of storage.
Editorial Material
Chemistry, Organic
Gabriel A. S. Aquino, Floriano P. P. Silva-Jr, Sabrina B. B. Ferreira
Article
Biophysics
Caroline Deckmann Nicoletti, Raissa Maria dos Santos Galvao, Marcella de Sa Haddad Queiroz, Lais Barboclher, Ana Flavia Martins Faria, Guilherme Pegas Teixeira, Andre Luis Ameida Souza, Fernando de Carvalho da Silva, Vitor Francisco Ferreira, Camilo Henrique da Silva Lima, Luana P. Borba-Santos, Sonia Rozental, Debora Omena Futuro, Robson Xavier Faria
Summary: The subclass naphthoquinone includes several compounds that are effective against various pathogenic microorganisms. In this study, the antiparasitic and antifungal activities of O-allyl-lawsone (OAL) and OAL encapsulated in 2-hydroxypropyl-β-cyclodextrin (OAL MKN) were evaluated. The results showed that OAL MKN exhibited higher selectivity and lower cytotoxicity compared to the free form, making it a potential agent for treating neglected diseases.
JOURNAL OF BIOENERGETICS AND BIOMEMBRANES
(2023)
Review
Biochemistry & Molecular Biology
Mario M. Q. Simoes, Jose A. S. Cavaleiro, Vitor F. Ferreira
Summary: Diazo compounds are widely used in organic synthesis, catalyzed by transition metals with various ligands to modulate the selectivity and capacity of the catalyst. Porphyrins have been found to be efficient catalysts for diazo compound reactions, especially when complexed with low-cost metals. Recent research has focused on metalloporphyrin-catalyzed reactions and the potential applications of artificial metalloenzymes and hemoproteins.
Article
Chemistry, Multidisciplinary
Cristina Moll Huether, Wilson C. Santos, Fernando de Carvalho da Silva, Luana da Silva Magalhaes Forezi, Patricia Garcia Ferreira, Vitor Francisco Ferreira
Summary: This article aims to demonstrate the diversity of natural alkaloids and their applications in treating diseases from a didactic, historical, and biological perspective. It highlights the importance of conserving forests as many drugs are derived from them. The article also emphasizes the consequences of forest destruction, including the extinction of biodiversity and the loss of potential new bioactive substances, impacting communities dependent on forests.
REVISTA VIRTUAL DE QUIMICA
(2023)
Article
Chemistry, Multidisciplinary
Luana S. Gomes, Erica O. Costa, Thuany G. Duarte, Mateus H. Kohler, Bruna M. Rodrigues, Vitor F. Ferreira, Fernando de C. da Silva, Bernardo A. Iglesias, Vanessa Nascimento
Summary: This study presents a comprehensive analysis of a novel series of chalcogen-naphthoquinone-1,2,3-triazole hybrids, including their synthesis, structural elucidation, photophysical behavior, and electrochemical properties. These hybrids were synthesized with remarkable efficiency and exhibit exceptional photophysical and electrochemical properties, promising potential applications in biological assays.
Article
Chemistry, Multidisciplinary
Patricia G. Ferreira, Cristina M. Huther, Wilson C. Santos, Luana da Silva Magalhaes Forezi, Fernando de Carvalho da Silva, Vitor Francisco Ferreira
Summary: Forests represent the continuity of life and are essential for social and economic development. However, their existence is threatened by human greed and irresponsibility, leading to climate change and devastating events. Forests also serve as valuable resources for non-timber forest products, which can bring economic benefits.
REVISTA VIRTUAL DE QUIMICA
(2023)
Article
Chemistry, Multidisciplinary
Patricia Garcia Ferreira, Debora O. Futuro, Luana da Silva Magalhaes Forezi, Fernando de Carvalho da Silva, Vitor Francisco Ferreira
Summary: Surfactants, organic substances with amphiphilic behavior, are widely used in commercial products. Their hydrophobic and hydrophilic properties are crucial for formulation stability. Finding sustainable alternatives to petroleum-based surfactants remains a challenge.
REVISTA VIRTUAL DE QUIMICA
(2023)
