Article
Chemistry, Multidisciplinary
Aimin Xu, Xiaoyu Zhou, Rimei Zheng, Zhijing Zhang, Xinru Yin, Kemiao Hong, Zhuofeng Ke, Yu Qian, Wenhao Hu
Summary: In this study, a chiral dirhodium complex was used as a catalyst for asymmetric annulation reactions, leading to the synthesis of chiral 2,3-dihydropyrans with excellent diastereos-electivities and enantioselectivities. The high stereoselectivity of the products was elucidated through experimental and computational studies. Furthermore, these chiral products exhibited potent antiproliferation activity against three cancer cell lines.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Infectious Diseases
Arancha Lopez-Perez, Stefan Freischem, Immanuel Grimm, Oliver Weiergraeber, Andrew J. Dingley, Maria Pascual Lopez-Alberca, Herbert Waldmann, Waldemar Vollmer, Kamal Kumar, Cuong Vuong
Summary: The study identified a potential inhibitor of PBP3 through a fluorescence assay and chemical optimization, showing excellent target inhibition against P. aeruginosa and no apparent cytotoxicity. Further optimization is needed to improve antibacterial activity.
Article
Chemistry, Multidisciplinary
Dipika Narula, Shamsher S. Bari, Pooja Yadav, Sadhika Khullar, Sanjay K. Mandal, Gurpreet Kaur, Ganga Ram Chaudhary, Aman Bhalla
Summary: Monocyclic azetidin-2,3-diones can be easily extended to spiro-fused azetidin-2-ones through cyclocondensation reaction catalyzed by p-toluenesulfonic acid. The products were obtained in good yields within a short timeframe, and the stereochemical and spectroscopic studies confirmed the configuration of the spiro-fused products.
Article
Chemistry, Organic
O. A. Myshkina, S. S. Kharitonova, S. Y. Balandina, R. R. Makhmudov, N. Y. Lisovenko
Summary: The reaction between 5-substituted 4,4,4-trichloroacetylfuran-2,3-diones and aromatic amines led to the formation of 4-substituted 5-hydroxy-5-(trichloromethyl)dihydrofuran-2,3-diones, which exhibited antibacterial and antinociceptive activity.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Velmurugan Tamilselvi, Cinnathambi Subramani Maheswari, Appaswami Lalitha
Summary: A new, efficient one-pot three-component synthesis of oxindole derivatives has been developed, offering excellent yields, shorter reaction time, readily available starting materials, and mild reaction conditions. This method avoids the use of expensive catalysts and toxic solvents, making it a simple and effective synthetic approach.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Rayhaneh Alipoor, Mohammad Reza Mohammadizadeh, Dariush Saberi
Summary: This study reports the synthesis of two important families of organic compounds using one-pot three-component methods. The reactions were carried out using new starting materials and the products were identified using IR, H-1- and C-13-NMR spectra. The NMR spectra of some products showed asymmetric properties and the presence of diastereomers, as well as the formation of nonplanar eight-membered rings.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Multidisciplinary
V. L. Gein, D. A. Naif, E. Pastukhova, I. P. Yakovlev
Summary: The reaction in glacial acetic acid resulted in the synthesis of ethyl 4-[5-aryl-3-hydroxy-2-oxo-4-(4-chlorobenzoyl)-2,5-dihydro-1H-pyrrol-1-yl]benzoates.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
H. C. Yuan, L. X. Xu, N. H. Wang, H. B. Leng, S. W. Que
Summary: This study discovered a compound named SNA that has inhibitory effects on neuroglioma by increasing apoptosis to suppress cell proliferation and migration. This suggests that SNA has the potential to be a drug for treating neuroglioma.
PHARMACEUTICAL CHEMISTRY JOURNAL
(2022)
Article
Chemistry, Physical
Ram Naresh Yadav, Aarif Latif Shaikh, Aparna Das, Devalina Ray, Bimal Krishna Banik
Summary: The aim of this study is to investigate the p-toluene sulphonic acid (p-Ts.OH)-catalyzed reaction of racemic-azetidine-2,3-diones with enantiomerically pure cis and trans-4-hydroxy-L-proline in refluxing ethanol, resulting in the synthesis of substituted novel 3-(pyrrol-1-yl)-azetidin-2-ones at the C-3 position. An alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the beta-lactams ring, was described. All four diastereomers of 3-(pyrrol-1-yl)-azetidin-2-ones could be achieved in good to excellent yield with high diastereoselectivity in a single-pot operation. This method can be applied to other activated carbonyl compounds, and functionalized pyrroles can be obtained through an expeditious process.
CURRENT ORGANOCATALYSIS
(2022)
Article
Food Science & Technology
Kang Li, Dawei Yuan, Wei Chen, Rulan Ma, Yinsheng Xian
Summary: A new compound called (S)-(-)-N-[2-(3-Hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-ethyl]-acetamide (EA), isolated from Selaginella pulvinata, has been found to possess anti-proliferative effects against SK-mel-110 cells. In this study, EA was investigated for its potential antitumor effects against colon cancer. The results showed that EA could induce apoptosis of colon cancer cells and inhibit colon tumor growth in mouse models. Additionally, EA treatment also affected the tumor microenvironment by reducing suppressor cell accumulation and increasing tumor infiltrating lymphocytes.
FOOD SCIENCE AND TECHNOLOGY
(2022)
Article
Ophthalmology
Dawei Wang, Qing Li, Yue Wang, Yuanchun Jiang
Summary: SA significantly inhibited the proliferation of melanoma cells and induced apoptosis and autophagy, possibly through the PI3K/Akt and MAPK signaling pathways. Additionally, SA treatment effectively slowed melanoma tumor growth, as evidenced by decreased tumor volume and weight.
CUTANEOUS AND OCULAR TOXICOLOGY
(2021)
Article
Chemistry, Inorganic & Nuclear
N. colak, A. Karayel, K. Buldurun, N. Turan
Summary: In this study, a series of Schiff base compounds were synthesized and characterized using various spectroscopic methods, with the crystal and molecular structure of compound 2a determined by X-ray crystallographic analysis. Results showed the presence of two intramolecular hydrogen bonds in compound 2a, while compound 2b and 2c did not exhibit this type of interaction.
JOURNAL OF STRUCTURAL CHEMISTRY
(2021)
Article
Chemistry, Applied
Irene Martin, Cristina Aragoncillo, Pedro Almendros
Summary: This research has achieved a selective palladium-catalyzed reaction sequence, leading to the synthesis of novel 2-iodo-1-aryl-9H-carbazoles. The observed formation of 2-iodocarbazoles in contrast to gold catalysis suggests a metal-controlled cyclization through chemo- and regioselective alkyl migration and iodonium migration.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Jose M. Alonso, Pedro Almendros
Summary: The allene functionality, specifically the allenol, has evolved from a chemical curiosity to a common building block in modern organic chemistry, with unique reactivity and frequent occurrence in naturally systems. This Review highlights the significant contributions to the chemistry of allenols in the past decade, focusing on their synthesis, reactivity, and presence in natural products.
Article
Chemistry, Organic
Carlos Lazaro-Milla, Hikaru Yanai, Pedro Almendros
Summary: A new sequential cyclization cascade method has been successfully developed in this study for the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters.
Article
Chemistry, Applied
Fernando Herrera, Pablo Esteban, Amparo Luna, Pedro Almendros
Summary: The synergy between metal catalysis and radical chemistry has enabled researchers to overcome previous limitations in reactions between allenols and sulfonylating reagents, leading to successful copper-catalyzed cascade cycloetherification/sulfonylation for the controlled preparation of specific products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Shoki Hoshikawa, Hikaru Yanai, Irene Martin-Mejias, Carlos Lazaro-Milla, Cristina Aragoncillo, Pedro Almendros, Takashi Matsumoto
Summary: The carboarylation reaction of biphenyl-alkynes was successfully initiated by electrophilic attack of 1,1-bis(triflyl)ethylene on the alkyne moiety, resulting in polycyclic aromatic hydrocarbons decorated with superacidic carbon acid functionality. Neutralization of the obtained acids with NaHCO3 produced sodium salts with improved solubility in both aqueous and organic solvents.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Carlos Lazaro-Milla, Pedro Almendros
Summary: This study presents a sustainable and efficient synthesis of new quinoline derivatives with one or two SO2CF3 groups, without the need for metal, catalyst, or irradiation. The method uses readily available and stable precursors, avoiding the formation of side products, while being able to tolerate a wide range of functional groups under mild conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Irene Martin-Mejias, A. Sonia Petcu, Jose M. Alonso, Cristina Aragoncillo, Pedro Almendros
Summary: The controlled access to 1-aryl 2,3-diiodo-carbazoles involving iodine transposition has been achieved directly from acyclic precursors. The 2,3-diiodo-carbazole core is susceptible to further chemoselective decoration at C3-I or double difunctionalization.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Mireia Toledano-Pinedo, Teresa Martinez del Campo, Hikaru Yanai, Pedro Almendros
Summary: This study presents a gold-catalyzed bis[(trifluoromethyl)sulfonyl]ethylation of alpha-allenols, allowing the synthesis of sterically congested bis(triflyl)enals with quaternary carbon centers. The reaction pathway is different from the conventional approach, as Au(I) acts as a pi-Lewis base catalyst instead of a pi-Lewis acid, activating the allene and facilitating the unusual addition of a carbon nucleophile from the gold complex belonging to the allenol moiety. Density functional theory calculations were performed to understand this unique pathway.
Review
Chemistry, Applied
Jose M. Alonso, Pedro Almendros
Summary: Conjugated and non-conjugated allenones are widely used in organic synthesis, natural products, and mechanistic investigations due to their unique properties and applications. Their ability to form cycles allows for the preparation of strained systems, medium-sized rings, arenes, heterocycles, and complex polycycles. This comprehensive review provides an overview of the synthetic possibilities offered by allenones, inspiring the organic chemistry community in their search for more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and advancing theoretical organic chemistry knowledge. The review also discusses synthetic aspects, catalysis innovation, and mechanistic insights related to the allenone motif, as well as examples of total synthesis and pharmacologically active compounds. It aims to attract researchers from various fields including organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products, and medicinal chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
A. Sonia Petcu, Carlos Lazaro-Milla, F. Javier Rodriguez, Isabel Iriepa, Oscar M. Bautista-Aguilera, Cristina Aragoncillo, Jose M. Alonso, Pedro Almendros
Summary: Here, a convenient preparation method for isocoumarin and isoquinolone is described, which involves an initial bis(triflyl)ethylation reaction followed by heterocyclization. The efficiency of the reaction depends on the substituents' electronic nature in the precursors. Molecular docking of the obtained isocoumarins showed promising biological activities on human acetylcholinesterase.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Diego G. Matesanz, Laura Gamarra, Teresa Martinez del Campo, Pedro Almendros, Sara Cembellin
Summary: A highly selective Mn(I)-catalyzed dienylation of arenes and heteroarenes with acetylated allenes is reported. The method proceeds through a one-pot procedure and delivers linear 1,3-dienes as single products with high stereoselectivity and total regioselectivity. This strategy shows wide functional group tolerance and preparative scale utility, making it efficient for late-stage functionalization of complex valuable molecules. The synthetic importance is highlighted by different derivatizations of the final products, which can exhibit interesting fluorescence properties.
Article
Chemistry, Organic
Hikaru Yanai, M. Rosa Marquez, Sara Cembellin, Teresa Martinez del Campo, Pedro Almendros
Summary: An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, allowing the synthesis of substituted gamma-methylenebutenolides in water, has been achieved. This process differs from the established reactivity of unsaturated organic halides and carbonyls mediated by metals. The use of water as a medium and the ease of purification make this protocol a convenient and sustainable synthetic strategy. A plausible reaction pathway has been proposed with the aid of density functional theory calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Mireia Toledano-Pinedo, Teresa Martinez del Campo, Hikaru Yanai, Pedro Almendros
Summary: The gold-catalyzed bis[(trifluoromethyl)sulfonyl]ethylation of alpha-allenols, allowing the synthesis of sterically congested bis(triflyl)enals with quaternary carbon centers, is presented. In this reaction, a unique pathway is observed where Au(I) acts as a pi-Lewis base catalyst instead of a pi-Lewis acid to activate the allene, enabling the unusual addition of a carbon nucleophile. Density functional theory calculations were conducted to analyze this unconventional pathway.
Article
Chemistry, Multidisciplinary
Carlos Lazaro-Milla, M. Teresa Quiros, Diego J. Cardenas, Pedro Almendros
Summary: The synthesis of skipped 1,4-enynes through functionalization of the cyclobutene core with alkynes has been achieved, indicating an unusual pathway of oxidative addition in tertiary iodoalkanes.
CHEMICAL COMMUNICATIONS
(2021)