Article
Chemistry, Multidisciplinary
Joshua D. Tibbetts, William B. Cunningham, Massimiliano Vezzoli, Pawel Plucinski, Steven D. Bull
Summary: The solvent-free continuous flow epoxidation of a range of biorenewable terpene substrates using a recyclable tungsten-based polyoxometalate phase transfer catalyst and aqueous H2O2 as an oxidant enables efficient and safe production of epoxides in commercial microreactors. These procedures are applicable for the safe production of multigram quantities of a wide range of epoxides from trisubstituted and disubstituted alkenes.
Article
Chemistry, Multidisciplinary
Yang Xi, Wenyi Huang, Chenchen Wang, Haojie Ding, Tingting Xia, Licheng Wu, Ke Fang, Jingping Qu, Yifeng Chen
Summary: This study reports a new catalyst system for the enantioselective transformation of internal acyclic alkenes. By applying different reaction types to two common acyclic alkenes, products with asymmetric centers were obtained. Moreover, the formation of incontiguous stereocenters was achieved through an interrupted chain-walking process.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Shobhon Aich, Rajesh Nandi, Nirbhik Chatterjee, Krishnanka S. S. Gayen, Subhasis Pal, Dilip K. K. Maiti
Summary: We developed an efficient I-2-catalyzed strategy for the synthesis of functionalized alpha-amidohydroxyketones and symmetrical and unsymmetrical bisamides using benzimidate scaffolds and moist-DMSO. The broad substrate scope and moderate yields are the key advantages of this approach. High-resolution mass spectrometry and labeling experiments provided evidence for the mechanism, and H-1 nuclear magnetic resonance titration revealed the recognition property of the synthesized compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yichen Sun, Zhibin Hu, Jing Peng, Qixue Qin, Ning Jiao
Summary: The Baeyer-Villiger oxidation is a valuable reaction for converting ketones into esters or lactones. In this study, a novel and efficient approach utilizing I-2 as a catalyst for the oxidative rearrangement of cyclobutenones was presented, resulting in the synthesis of furan-2(5H)-one. Dimethyl sulfoxide (DMSO) was used as a greener oxidant and source of oxygen. The reaction proceeded smoothly with catalytic amounts of iodine, yielding lactones in good yields. Compared to conventional Baeyer-Villiger oxidation reactions, the use of DMSO offers a safer and more versatile alternative.
Article
Chemistry, Organic
Subban Kathiravan, Prasad Anaspure
Summary: This paper reports an electrochemical intermolecular C-H/N-H oxidative annulation of 2-phenylpyrazoles with alkynes using a rhodium(iii) redox regime without external metal oxidants, in a water compatible solvent system. Both symmetrical and unsymmetrical alkynes were found to be compatible with the optimized conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jun Dong, Duo Fu, Dongning Sheng, Jiayi Wang, Jiaxi Xu
Summary: The study demonstrates that N-arylethynylsulfonamides can be efficiently oxidized into N-sulfonyl-2-aryloxoacetamides directly with dimethyl sulfoxide (DMSO) serving as both an oxidant and solvent, in the presence of microwave assistance. The reaction mechanism involves nucleophilic attack by DMSO on the ethylic triple bond, leading to the formation of zwitterionic anionic N-sulfonyliminiums that trigger the oxidation reaction. This method provides a straightforward and efficient strategy for the transformation of various N-arylethynylsulfonamides without the need for other electrophilic activators or oxidants.
Article
Chemistry, Organic
Swadhapriya Bhukta, Rana Chatterjee, Rambabu Dandela
Summary: A novel and efficient method for the synthesis of substituted imidazoles has been developed using the I-2-DMSO concerted system. The reactions proceed efficiently in solvent-free conditions, resulting in good yields of various substituted imidazoles. This method offers advantages such as metal- and solvent-free process, mild conditions, and easily accessible reactants.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Mingxia Zhang, Wenzuo Li, Ziyan Zhou, Shuping Zhuo, Zhongmin Su
Summary: This study investigates the hydrothiolation reactions of thiophenol and allylamine using an external electric field (EEF) as a catalyst. The calculation results show that the orientation of the EEF affects the reaction pathway and barrier. The study also considers the solvent effects.
Article
Chemistry, Organic
Kusum Ucheniya, Amreen Chouhan, Lalit Yadav, Pooja Kumari Jat, Satpal Singh Badsara
Summary: We report a mild, scalable, electricity-promoted protocol for the cross coupling of allylic iodides and disulfides/diselenides to form C-S/Se bonds without the need for transition metals, bases, or oxidants. Different stereochemically diverse allylic iodides gave regio- and stereoselective thioethers in good yields. This strategy provides a sustainable and promising approach for the synthesis of allylic thioethers with yields ranging from 38% to 80%. Additionally, this protocol serves as a synthetic platform for the synthesis of allylic selenoethers. The involvement of a single-electron transfer radical pathway was confirmed through radical scavenger experiments and cyclic voltammetry data.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Siliang Ming, Jian Yang, Shi Wu, Gang Yao, Hongwei Xiong, Yu Du, Jun Gong
Summary: An efficient asymmetric cyclopropanation reaction has been developed, which involves the reaction of sulfoxonium ylides with alpha,beta-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex. The enantioenriched cyclopropane derivatives, containing three contiguous tertiary stereocenters, were obtained with high yields and excellent stereoselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Ali Nakhaei Pour, Ali Mohammadi
Summary: This study investigated the effect of synthesis conditions on the crystal growth, structural features, acidity, and catalytic properties of hierarchical ZSM-5 zeolite in n-heptane cracking. The results showed that the crystallization rate of hierarchical ZSM-5 increased with the amount of SiO2 and Na2O in the initial gel, as well as the reaction temperature. Additionally, by adjusting the initial gel composition and reaction temperature, the porosity, acidity, and crystal size of hierarchical ZSM-5 could be controlled. The selectivity of ethylene and propylene in the heptane cracking reaction was found to be influenced by the acidity and micropore to mesopore ratio of the prepared zeolites, as predicted by both experimental and simulation results.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Xia Xiao, Zhongliang Xu, Peng Wang, Xinfei Liu, Xiaoqiang Fan, Lian Kong, Zean Xie, Zhen Zhao
Summary: The solvent-free synthesis methodology was used to prepare SAPO-34 zeolite with adjustable crystal size, texture properties, acidity, and Si coordination environment by tuning the SiO2/Al2O3 molar ratio. The resulting zeolite exhibited high conversion and yield in the catalytic cracking of 1-butene, attributed to the synergistic effect of large surface area and abundant acid sites. This work opens up a new opportunity for designing efficient zeolite catalysts for industrially important reactions.
Article
Chemistry, Organic
Sumedha Swarnkar, Mohd Yeshab Ansari, Atul Kumar
Summary: This study presents a novel visible-light-induced one-pot tertiary C(sp(3))-H sulfonylation reaction, providing a new strategy for late-stage functionalization of pharmaceutical compounds and their analogues.
Article
Materials Science, Multidisciplinary
Youhe Wang, Tingting Li, Chencan Li, Jinzhi Lu, Chang Dai, Fazle Subhan, Peng Bai, Hongman Sun, Rui Feng, Zifeng Yan
Summary: The development of a sustainable synthesis route for Fe-ZSM-5 zeolites is important for their diverse applications. A novel dry gel conversion method was reported for one-pot synthesis of Fe-ZSM-5 zeolites, which does not require adding templates or seed crystals, improving synthesis efficiency and reducing environmental pollution. Characterization results showed that Fe-ZSM-5-In has enhanced acid amount and better distribution of framework Fe3+ species compared to Fe/ZSM-5-Im.
JOURNAL OF MATERIALS SCIENCE
(2021)
Review
Biochemistry & Molecular Biology
Flavio A. R. Barbosa, Romulo F. S. Canto, Kerolain F. Teixeira, Anacleto S. de Souza, Aldo S. de Oliveira, Antonio L. Braga
Summary: Alzheimer's disease (AD) is a prevalent type of dementia that affects millions of older people worldwide. Selenium-containing compounds have shown potential as multi-targeted drugs for the treatment of AD due to their antioxidant and anticholinesterase properties. These compounds can decrease the aggregation of amyloid-beta (A beta), a key feature of AD. Some selenium-derived compounds have molecular features similar to FDA-approved drugs, suggesting that they may have optimized pharmacokinetic properties.
CURRENT MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Caroline S. B. Weber, Aline Tavares, Bruno Bercini de Araujo, Rebeca O. Costa, Taise M. Manhabosco, Bruna B. Postacchini, Andre A. Vieira, Thiago Cazati, Aloir A. Merlo
Summary: This study designed and synthesized two dyes with an alkoxy group as a donor connected to cyanoacrylic acid acceptor/anchoring group bridged by the phenylacetylene unit. The dyes were characterized and their properties were investigated. The results showed that the dyes exhibited thermal instability at high temperatures and fluorescence quenching in the solid state.
Article
Toxicology
Raffaella di Vito, Sara Levorato, Cristina Fatigoni, Mattia Acito, Luca Sancineto, Giovanna Traina, Milena Villarini, Claudio Santi, Massimo Moretti
Summary: PhSeZnCl has been shown to exhibit cytotoxic and apoptotic activities in preclinical hepatic cell models, with a stronger effect observed in HepG2 tumor cells. It can cause DNA damage, cell cycle arrest, mitochondrial membrane depolarization, and induction of apoptosis. These findings provide new insights into the biological activity of PhSeZnCl and its potential as a pharmaceutical compound.
TOXICOLOGICAL RESEARCH
(2023)
Review
Biochemistry & Molecular Biology
Davide Benedetto Tiz, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Luca Sancineto, Claudio Santi
Summary: This review discusses the top-selling small molecule orphan drugs based on their sales projections for 2026. Orphan drugs are designed to treat, prevent, or diagnose rare diseases or conditions. Most of these molecules target rare forms of cancer, with respiratory and central nervous systems being other commonly treated subcategories. The study highlights the significant growth of the orphan drugs market and its expected contribution to prescriptions by 2026.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Joyce C. Oliveira, Renato L. de Carvalho, Hugo G. S. Sampaio, Joao Honorato, Javier A. Ellena, Felipe T. Martins, Joao V. M. Pereira, Pedro M. S. Costa, Claudia Pessoa, Rafaela S. Ferreira, Maria H. Araujo, Claus Jacob, Eufranio N. da Silva Junior
Summary: Our research group successfully combined two redox centres (ortho-quinone/para-quinone or quinone/selenium-containing triazole) through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, leading to significant anticancer activity. We synthesized 15 new quinone-based derivatives and evaluated their efficacy in nine cancer cell lines and the fibroblast line L929. Our study confirmed the effectiveness of A-ring functionalized para-quinones coupled with ortho-quinones in obtaining diverse two redox centre compounds with potential applications against cancer.
Article
Biochemistry & Molecular Biology
Mauricio Tavares Jacques, Viviane de Souza, Flavio Augusto Rocha Barbosa, Romulo Faria Santos Canto, Samantha Cristiane Lopes, Rui Daniel Prediger, Antonio Luiz Braga, Michael Aschner, Marcelo Farina
Summary: Oxidative glutamate toxicity is a harmful mechanism in ischemic stroke. Two new probucol analogues (C1 and C2) were designed and synthesized, and their effects against glutamate-induced neuronal oxidative toxicity were investigated. C2 showed the lowest toxicity and provided significant protection against glutamate-induced cytotoxicity both in vitro and in vivo. This study presents a promising neuroprotective drug for ischemic stroke.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Biochemistry & Molecular Biology
Rama Alhasan, Guilherme M. Martins, Pedro P. de Castro, Rahman Shah Zaib Saleem, Ali Zaiter, Isabelle Fries-Raeth, Alexandra Kleinclauss, Caroline Perrin-Sarrado, Patrick Chaimbault, Eufranio N. da Silva Junior, Caroline Gaucher, Claus Jacob
Summary: Decreased selenium levels and increased oxidative stress have been linked to chronic diseases. This study synthesized and evaluated a series of organic selenium compounds for their antioxidant activities. The seleno-hydantoin derivatives exhibited glutathione peroxidase-like activity and show potential for treating chronic diseases.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Davide Zeppilli, Andrea Madabeni, Luca Sancineto, Luana Bagnoli, Claudio Santi, Laura Orian
Summary: This study investigates the reduction mechanism of H2O2 catalyzed by PhSeZnCl using density functional theory calculations. The impact of metal and halogen substitutions on catalytic activity is evaluated. It is found that Zn is a favorable catalytic metal, while halogen substitution has little effect. The overall mechanism of PhSeZnCl and PhSeZnBr is discussed.
INORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Martina Palomba, Italo Franco Coelho Dias, Michelangelo Cocchioni, Francesca Marini, Claudio Santi, Luana Bagnoli
Summary: A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed.
Article
Chemistry, Multidisciplinary
Carlos V. Doerner, Jose S. S. Neto, Climei R. Cabreira, Sumbal Saba, Louis P. Sandjo, Jamal Rafique, Antonio L. Braga, Francisco F. de Assis
Summary: Here, an original and sustainable synthetic methodology for the synthesis of 3-selanyl-isoflavones from 2-hydroxyphenyl enaminones and diorganoyl diselenides is presented. The reaction, promoted by trichloroisocyanuric acid and using ethanol as a solvent, proceeds in a one-pot manner under mild conditions. Using this protocol, 22 examples of 3-selanyl-isoflavones were prepared in yields ranging from 34% to 95%.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mateus P. Nunes, Dhanaji V. Jawale, Fabio G. Delolo, Maria H. Araujo, Edmond Gravel, Eric Doris, Eufranio N. da Silva Junior
Summary: A heterogeneous catalyst composed of rhodium-ruthenium particles immobilized on carbon nanotubes was used in hydroboration reaction and showed high effectiveness for various alkenes and alkynes. The reactions were conducted with low catalytic loadings (0.04 mol%), solvent-free conditions, and at room temperature. Additionally, the catalyst demonstrated recyclability by being recovered through a simple centrifugation process and reused for 5 consecutive cycles without any loss in activity.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Inorganic & Nuclear
Kamil Bugaj, Patrycja Pokora-Sobczak, Grazyna Mielniczak, Luca Sancineto, Claudio Santi, Jozef Drabowicz
Summary: This paper presents the use of ball milling in organic synthesis, focusing on the formation and transformation of sulfur-containing functional groups. The results of sulfenylation reactions, coupling reactions, redox reactions, and condensation reactions under mechanochemical conditions are summarized. This review aims to provide a useful addition to the existing literature on mechanochemistry and attract more researchers' attention to the attractive features of mechanochemical protocols.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2023)
Article
Optics
Weder Junior Elias de Paula, Gustavo de Almeida Magalhaes Safar, Eufranio N. da Silva Jr, Luiz A. Cury
Summary: This study investigates phosphorescent emissions at room temperature from a solid-state self sustained film fabricated using phenazine derivative molecules blended in a solution of poly(methyl methacrylate). The results show that the film exhibits relatively higher gain characteristics for triplet state excitons, enabling waveguided emission. The analysis of the emission spectra indicates a relatively higher contribution of the total integrated area for the phosphorescent part.
JOURNAL OF LUMINESCENCE
(2024)
Article
Chemistry, Multidisciplinary
Esther S. Areas, Bruno P. Rodrigues, Ana Carolina C. do Nascimento, Henrique C. Silva Junior, Glaucio B. Ferreira, Fabio S. Miranda, Flavio Garcia, Syed H. Safeer, Stephane Soriano, Guilherme P. Guedes
Summary: A series of mononuclear lanthanide-based coordination compounds were successfully synthesized and characterized. The compounds exhibited various luminescent and magnetic properties, suggesting potential applications.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Renato L. de Carvalho, Emilay B. T. Diogo, Simon L. Homoelle, Suman Dana, Eufranio N. da Silva Junior, Lutz Ackermann
Summary: Transition-metal catalyzed C-H activation reactions are effective methods for synthesizing important molecules. Understanding the role of silver salts as additives can help overcome the challenges associated with their use and shift towards silver-free systems.
CHEMICAL SOCIETY REVIEWS
(2023)
