Article
Biochemistry & Molecular Biology
Spyridon Mourtas, Vasileios Athanasopoulos, Dimitrios Gatos, Kleomenis Barlos
Summary: In this study, a facile and efficient method for the solid-phase synthesis of chiral-pure BTH and AP-BTH C-terminal modified amino acids and peptides was developed.
Article
Chemistry, Multidisciplinary
Hsing-Yu Chen, Chen-Chen Yao, Tzu-Yu Tseng, Yao-Chun Yeh, He-Shin Huang, Mei-Yu Yeh
Summary: This study synthesized benzoxazolyl-imidazole and benzothiazolyl-imidazole conjugates with aggregation-induced emission (AIE) features. Sulphur-nitrogen interactions contributed to the AIE phenomenon and resulted in different fluorescence emission properties in aqueous solution.
Article
Chemistry, Medicinal
Hanxi Yang, Mengyuan You, Xiaoyang Shu, Jingyao Zhen, Mengwei Zhu, Tiantian Fu, Yan Zhang, Xiangrui Jiang, Leike Zhang, Yechun Xu, Yumin Zhang, Haixia Su, Qiumeng Zhang, Jingshan Shen
Summary: A series of peptidomimetic compounds containing benzothiazolyl ketone and [2.2.1] azabicyclic ring were synthesized and evaluated for their inhibition of SARS-CoV-2 3CLpro. Compound 11j showed the best enzyme inhibition activity and exhibited significant anti-SARS-CoV-2 activity with low cytotoxicity. It displayed promising pharmacokinetic properties and could serve as a lead compound for further development of oral 3CLpro inhibitors.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Analytical
Aisha Hossan, Samar. Y. Y. Al-nami
Summary: The molecular structures of the synthesized benzothiazolyl-chromenone-based fluorophores were investigated using various spectral methods, and it was found that alkyl substituents on the benzothiazole bridge affected the maximum absorbance wavelength. The synthesized fluorophores exhibited significant absorption and emission effects, and showed antioxidant efficacy comparable to commonly used medications. Moreover, these synthesized fluorophores showed marked coordination with antioxidant efficacy in docking studies with the chosen 3NM8 protein.
Article
Chemistry, Organic
Maximilian Kaiser, David Schoenbauer, Katharina Schragl, Matthias Weil, Peter Gaertner, Valentin S. Enev
Summary: This paper describes our efforts towards the total synthesis of natural product elisabethin A. The first approach focuses on the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach involves a high yielding cyclization under Mitsunobu conditions as a key step, leading to the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an underdeveloped Claisen rearrangement of an aryl dienyl ether.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Changjiu Sun, Yuanzhi Jiang, Li Zhang, Keyu Wei, Mingjian Yuan
Summary: Lead halide perovskite nanocrystals (LHP NCs) have great potential in optical sources, photovoltaics, and sensor fields. This Perspective summarizes representative attempts to achieve controlled synthesis of LHP NCs. By changing the synthesis method, LHP NCs with kinetic dominance and size tunability can be obtained. Undesired ripening effects can be eliminated, and homogeneous size distribution can be achieved through rational ligand selection and solvent engineering.
Article
Chemistry, Organic
P. S. Bobrov, A. A. Kondrasenko, G. A. Suboch
Summary: The cyclocondensation reaction of 2-hydrazinylbenzothiazole with 2-(hydroxyimino)-1,3-diketones has been studied for the first time, yielding a series of previously unknown benzothiazolylnitrosopyrazoles. The synthesized compounds were characterized by various spectroscopic techniques and elemental analysis.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
HtooTint Wai, Thomas Koelblen, Matthew E. Hayes, Thomas P. Burris, Glenn C. Micalizio
Summary: Progress has been made in the asymmetric synthesis of euphanes, and a C14-desmethyl euphane system with five differentially substituted and electronically distinct alkenes has been successfully prepared. The route employed involves sequential metallacycle-mediated annulative cross-coupling, double asymmetric Bronsted acid mediated intramolecular Friedel-Crafts alkylation, and an oxidative rearrangement to establish the required C10 quaternary center. These studies have also led to the discovery of a novel euphane-based modulator of the Liver X Receptor.
Review
Chemistry, Multidisciplinary
Ramsha Munir, Ameer Fawad Zahoor, Usman Nazeer, Muhammad Athar Saeed, Asim Mansha, Ahmad Irfan, Muhammad Umair Tariq
Summary: This review examines the applications of Gilman reagent in the total synthesis of both abundant and scarce natural products, which provides important guidance for general organic synthesis and new drug development.
Review
Chemistry, Inorganic & Nuclear
Ricca Rahman Nasaruddin, Tiankai Chen, Qiaofeng Yao, Shuangquan Zang, Jianping Xie
Summary: The use of biomolecules from biological or biomimetic systems has emerged as a promising green approach to synthesize gold nanomaterials. Recent progress has been made in the biological and biomimetic syntheses of gold nanomaterials, focusing on selection principles of biomolecules, synthesis mechanisms, evolution from biological to biomimetic synthesis, and contributions to green production. This review aims to provide a guideline for the green synthesis of gold nanomaterials and other metal nanomaterials for practical applications in biomedicine.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Physical
Stefano Cestellos-Blanco, Sheena Louisia, Michael B. Ross, Yifan Li, Nathan E. Soland, Tyler C. Detomasi, Jessica N. Cestellos Spradlin, Daniel K. Nomura, Peidong Yang
Summary: This study provides a roadmap that evaluates the feasibility of using state-of-the-art electrochemical processes to convert CO2 into sugars, and identifies the crucial role of glycolaldehyde in sugar formation.
Article
Chemistry, Organic
Mengge Zhang, Yonggang Meng, Yangang Wu, Chuanjun Song
Summary: A novel solvent-free, TfOH-promoted decyanative cyclization method has been developed for the synthesis of 2,1-benzisoxazoles. The reactions are completed instantly at room temperature with yields ranging from 34-97%.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hannah M. S. Haley, Stefan E. Payer, Sven M. Papidocha, Simon Clemens, Jonathan Nyenhuis, Richmond Sarpong
Summary: By bioinspired late-stage diversification of a readily accessible common precursor, total syntheses of Lycopodium alkaloids can be achieved, including oxidative C-C bond cleavage of a piperidine ring in the core structure and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Materials Science, Multidisciplinary
Sylwia Glowniak, Barbara Szczesniak, Jerzy Choma, Mietek Jaroniec
Summary: Metal-organic frameworks (MOFs) are receiving special attention for their adjustable pore sizes and high potential in various applications, with mechanochemistry seen as an efficient and environmentally friendly synthesis method.
Article
Chemistry, Organic
Christian P. Bold, Cindy Klaus, Bernhard Pfeiffer, Jasmine Schurmann, Rafael Lombardi, Daniel Lucena-Agell, J. Fernando Diaz, Karl-Heinz Altmann
Summary: The synthesis of an oxazole-based analog of (-)-zampanolide was studied, with successful construction of (-)-dactylolide analog 22. However, attempts to attach (Z,E)-sorbamide failed, possibly due to the migration of the C(8)-C(9) double bond in the macrocycle. This limitation may affect the utility of zampanolide analogs with aromatic moieties as tetrahydropyran replacements.
Article
Chemistry, Organic
Cyril Lebargy, Coralie De Schutter, Remi Legay, Emmanuel Pfund, Thierry Lequeux
Article
Chemistry, Organic
Thibault Thierry, Cyril Lebargy, Emmanuel Pfund, Thierry Lequeux
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Infectious Diseases
Delphine Coupri, Aurelie Budin-Verneuil, Axel Hartke, Abdellah Benachour, Loic Leger, Thierry Lequeux, Emmanuel Pfund, Nicolas Verneuil
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY
(2019)
Article
Chemistry, Organic
Emmanuel Pfund, Christelle Dupouy, Sonia Rouanet, Remi Legay, Cyril Lebargy, Jean-Jacques Vasseur, Thierry Lequeux
Article
Chemistry, Organic
Clement Q. Fontenelle, Thibault Thierry, Romain Laporte, Emmanuel Pfund, Thierry Lequeux
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Thibault Thierry, Emmanuel Pfund, Thierry Lequeux
Summary: A metal-free alpha-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation was reported. Precursor of alpha-aminomethyl radical species, alpha-trimethylsilylamines, were used to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. Investigation of the mechanism suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle in this late-stage functionalization of aryls.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Infectious Diseases
Delphine Coupri, Nicolas Verneuil, Axel Hartke, Axelle Liebaut, Thierry Lequeux, Emmanuel Pfund, Aurelie Budin-Verneuil
Summary: The study investigates the potential of targeting D-alanylation of teichoic acids (TAs) mediated by the dlt operon gene products as a strategy to overcome beta-lactam resistance in MRSA. Results show that genetic or chemical inhibition of the Dlt system can resensitize MRSA to beta-lactam antibiotics, especially in combination with imipenem, offering a promising therapeutic approach for combating MRSA infections.
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY
(2021)
Article
Chemistry, Organic
Florent Larnaud, Charlene Calata, Anais Prunier, Clothilde Le Guen, Remi Legay, Emmanuel Pfund, Thierry Lequeux
Summary: This study describes the convergent and selective preparation of (Z)-monofluoroalkene-based dipeptide isosteres from functionalized fluorosulfones. The N-terminal amino group is introduced through a conjugate addition reaction of phthalimide onto fluorinated vinylsulfones containing alpha-amino-acid side chains, while the C-terminal motif is linked to the fluorovinylic peptide bond mimic via the Julia-Kocienski reaction between fluorosulfones and substituted aldehydes bearing alpha-amino-acid side chains.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Youssou Faye, Batoul Rkein, Antoine Bigot, Thierry Lequeux, Julien Legros, Isabelle Chataigner
Summary: The photocatalyzed dearomative reaction between various electron-deficient aromatic compounds and a non-stabilized azomethine ylide is successfully performed in a flow system using soluble Rose Bengal as the organic photocatalyst. This reaction provides a simple and efficient access to tridimensional pyrrolidino scaffolds with a tetrasubstituted carbon center at ring junction and can be performed in environmentally friendly conditions. Computational studies support the mechanism involving azomethine ylide as a reactive species toward the electron-poor arene.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
David Leparfait, Feng Xiao, Delphine Coupri, Sabrina Gueulle, Florie Desriac, Aurelie Budin-Verneuil, Nicolas Verneuil, Axel Hartke, Emmanuel Pfund, Thierry Lequeux
Summary: Tri- and tetra-substituted alkenes, including fluoroalkenes, were obtained via selective ring-opening reaction of functionalized oxetanes. By introducing adenine nucleic base, alkenyl and fluoroalkenyl derivatives were synthesized as potential nucleoside mimics and evaluated for their activity against DltA enzyme.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
