Article
Biochemistry & Molecular Biology
Joana L. C. Sousa, Helio M. T. Albuquerque, Armando J. D. Silvestre, Artur M. S. Silva
Summary: Betulinic acid was used as a starting material to synthesize a library of novel BA-derived compounds containing O- and N-heterocycles. Remarkably, the triterpene acts as a diastereoselective inducer in nitromethane conjugate addition reaction, and can also incorporate other heterocycles into its molecular structure using simple synthetic methods.
Article
Chemistry, Multidisciplinary
Joseph Benford-Ward, Sanaz Ahmadipour, Aliya Sembayeva, Louise Male, Richard S. Grainger
Summary: The synthesis of the naturally occurring (+)-dictyoxetane was achieved through catalytic asymmetric synthesis and the use of alternative methods. The study also investigated a range of related reactions to the synthesis target.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Wei Jie Teh, Oriol Pique, Qi Hang Low, Weihan Zhu, Federico Calle-Vallejo, Boon Siang Yeo
Summary: The study investigates the electroreduction of CO2 to synthesize methanol using renewable electricity. By developing catalysts with Ti3+ sites and oxygen vacancies, the reduction of formic acid to methanol was achieved with high efficiency and partial current density.
Article
Chemistry, Physical
Ryohei Doi, Koji Shimizu, Yuma Ikemoto, Masashi Uchiyama, Mikiko Koshiba, Atsushi Furukawa, Katsumi Maenaka, Satoshi Watanabe, Yoshihiro Sato
Summary: This study reports a nickel-catalyzed cascade reaction to construct a 3-acylbenzo[b]furan skeleton. Through reaction condition optimization, the catalyst loading could be reduced to 5-10 mol %, leading to the synthesis of various functionalized compounds. Stoichiometric study of nickel complexes and DFT calculations were conducted to support a possible reaction mechanism.
Article
Chemistry, Multidisciplinary
Jackson S. Henneveld, Farshad Shiri, Alireza Ariafard, Nigel T. Lucas, Alex C. Bissember, Bill C. Hawkins
Summary: The investigation and formalization of the distinctive dipole-transmissive dipolar cycloaddition (DTDC) methodology is reported. A DTDC procedure was developed by taking advantage of the structural complementarity of azide and diazoalkane 1,3-dipoles. This method allows for the rapid construction of functionalized polycyclic N-heterocycles through intramolecular azide-alkene 1,3-dipolar cycloadditions followed by N-derivatization and subsequent 1,3-dipolar cycloadditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Tobias Brueckner, Felipe Fantuzzi, Tom E. Stennett, Ivo Krummenacher, Rian D. Dewhurst, Bernd Engels, Holger Braunschweig
Summary: The study found that NHC-stabilised diboryne can undergo a high-yielding reaction with tetraethyldiphosphine at room temperature to form a B2P2 heterocycle, which can be oxidised to different ionic forms. With each oxidation step, the structure of the heterocycle changes, showing different forms.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Chenxiao Qi, Guillaume Force, Vincent Gandon, David Leboeuf
Summary: A novel method for haloamidation is introduced in this paper, providing new building blocks for drug discovery. This method overcomes some limitations of traditional reactions and the reaction mechanism is deeply studied, which is expected to promote the development of more complex transformations in this field.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jia-Yun Wang, He-Nan Shang, Di Liu, Si-Jia Li, Ya-Xuan Bai, Yu-Bo Liu, Jin-Sheng Liang
Summary: The paper investigates an efficient, low-cost, and high-stable heterogeneous catalyst for the dehydrogenation of formic acid. Through a co-reduction method, ultrafine nanoparticles of NiCoPd-CeOx supported on nitrogen phosphorus co-functionalized reduced graphene oxide (NPG) were synthesized and exhibited outstanding catalytic activity and stability. This catalyst shows potential for the practical application of formic acid in fuel cells.
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY
(2022)
Article
Chemistry, Multidisciplinary
Friedrich Wossidlo, Daniel S. Frost, Jinxiong Lin, Nathan T. Coles, Katrin Klimov, Manuela Weber, Tobias Boettcher, Christian Mueller
Summary: In this study, a novel phosphinine selenide was successfully synthesized and isolated for the first time, showing enhanced basicity and nucleophilicity compared to unsubstituted phosphinine. This compound exhibits distinct reactivity towards various reagents, paving the way for new perspectives in low coordination phosphorus chemistry.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Jinxiong Lin, Friedrich Wossidlo, T. Coles Nathan, Manuela Weber, Simon Steinhauer, Tobias Boettcher, Christian Mueller
Summary: In this study, a phosphinine-borane adduct was synthesized and characterized for the first time using crystallography. The reaction heavily depends on the substituents in the phosphorus heterocycle. In contrast, the reaction of B2H6 with different substituted phosphinines leads to an equilibrium between the starting materials and the adducts, determined by the Lewis basicity. The novel phosphinine-borane adduct exhibits rapid and facile reactivity towards phenylacetylene, forming a previously unknown dihydro-1-phosphabarrelene with styrene.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Jinxiong Lin, Friedrich Wossidlo, T. Coles Nathan, Manuela Weber, Simon Steinhauer, Tobias Boettcher, Christian Mueller
Summary: In this study, a phosphinine-borane adduct was synthesized and characterized for the first time. Additionally, a novel phosphabarrelenium salt was discovered.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Bo-Han Zhu, Yan-Xin Zheng, Wei Kang, Chao Deng, Jin-Mei Zhou, Long-Wu Ye
Summary: A non-noble metal catalyzed hydrative cyclization of aldehyde-ynamides has been developed for the efficient and practical synthesis of medium-sized lactams (7- to 9-membered rings), showing a totally inverse diastereoselectivity compared to traditional methods. The protocol delivers valuable medium-sized lactams in moderate to good yields with high diastereoselectivities. Additionally, a rational mechanism based on theoretical calculations has been proposed to explain the inversion of diastereoselectivity.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Akitoshi Shiotari, Septia Eka Marsha Putra, Yuichiro Shiozawa, Yuji Hamamoto, Kouji Inagaki, Yoshitada Morikawa, Yoshiaki Sugimoto, Jun Yoshinobu, Ikutaro Hamada
Summary: This study reveals the temperature-dependent adsorption structures of HCOOH on Cu(111) surface through experimental and theoretical simulations. Different adsorption states were observed at different temperatures, and the interactions between adsorbates play a crucial role in stability and catalytic activity.
Article
Chemistry, Physical
B. B. Xiao, L. Yang, H. Y. Liu, X. B. Jiang, B. Aleksandr, E. H. Song, Q. Jiang
Summary: The study systematically investigates the oxygen reduction reaction and oxygen evolution reaction of graphene materials embedded with TMN4 clusters (TM = Fe, Co, Ni) using density functional theory calculations. It demonstrates that the functionalization of graphene can dramatically alter the activity and stability of TMN4 clusters, offering new insights into the design of bifunctional oxygen electrodes.
APPLIED SURFACE SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Yan-Xin Duan, Yi-Tong Zhou, Zhen Yu, Dong-Xue Liu, Zi Wen, Jun-Min Yan, Qing Jiang
Summary: A Bi/CeOx catalyst with high current density, unprecedented production rate, and high Faradaic efficiency was developed for the generation of formic acid in aqueous media. The catalyst also exhibited favorable stability over 34 hours, offering a promising strategy for efficient CO2 electroreduction catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Paloma Narros-Fernandez, Mourad Chioua, Sonia A. Petcu, Daniel Diez-Iriepa, Laura Cerrada-Galvez, Celine Decouty-Perez, Alejandra Palomino-Antolin, Eva Ramos, Victor Farre-Alins, Ana Belen Lopez-Rodriguez, Alejandro Romero, Jose Marco-Contelles, Javier Egea
Summary: NLRP3 plays a role in various inflammatory diseases, making the development of NLRP3 inflammasome small inhibitors a current area of interest. New N-sulfonylureas were obtained by modifying a previously described NLRP3 inhibitor, MCC950, and these derivatives showed potent inhibitory effects on IL-1 beta release. Compound 4b exhibited the greatest effect, similar to MCC950, and also showed a reduction in caspase-1 activation and IL-1 beta processing. In silico predictions confirmed the safety profile of compound 4b, and in vitro and in vivo studies further supported its anti-inflammatory properties.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Daniel Diez-Iriepa, Isabel Iriepa, Francisco Lopez-Munoz, Jose Marco-Contelles, Dimitra Hadjipavlou-Litina
Summary: This study reports the synthesis and evaluation of nine novel heterobisnitrones as antioxidants, with hBN9 showing the highest activity. The results suggest that hBN9 may be a potent antioxidant with potential anti-inflammatory effects.
Review
Chemistry, Medicinal
Sylvain Grosjean, Irene Pachon-Angona, Michella Dawra, Bernard Refouvelet, Lhassane Ismaili
Summary: Alzheimer's disease is a common neurodegenerative disease in the older population, and the use of multitarget-directed ligand strategy can lead to the development of complex molecules with multiple pharmacophores as a treatment approach.
FUTURE MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Oscar M. Bautista-Aguilera, Jose M. Alonso, Marco Catto, Isabel Iriepa, Damijan Knez, Stanislav Gobec, Jose Marco-Contelles
Summary: Alzheimer's disease (AD) is a complex disorder characterized by impaired neurotransmission, protein misfolding, and oxidative stress. Compound 4, a N-hydroxy-N-propargylamide hybrid, shows potential as a multifunctional ligand for AD treatment with inhibitory activity, radical scavenging ability, and copper chelation.
Editorial Material
Chemistry, Multidisciplinary
Lhassane Ismaili
FRONTIERS IN CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Daniel Diez-Iriepa, Damijan Knez, Stanislav Gobec, Isabel Iriepa, Cristobal de los Rios, Isaac Bravo, Francisco Lopez-Munoz, Jose Marco-Contelles, Dimitra Hadjipavlou-Litina
Summary: Novel polyfunctionalized nitrones show potential antioxidant and neuroprotective properties in stroke treatment, with compound (Z)-N-benzyl-1-(2-(3-(piperidin-1-yl)propoxy)phenyl)methanimine oxide exhibiting significant antioxidant and neuroprotective activities.
Article
Biochemistry & Molecular Biology
Emna Choura, Fares Elghali, Paul J. Bernard, Dhouha Msalbi, Jose Marco-Contelles, Sami Aifa, Lhassane Ismaili, Fakher Chabchoub
Summary: Ten new compounds were synthesized using a simple and cost-efficient method. These compounds exhibited antiproliferative activity in two colorectal cancer cell lines.
Article
Multidisciplinary Sciences
Sebastien Pasquereau, Mathilde Galais, Maxime Bellefroid, Irene Pachon Angona, Stephanie Morot-Bizot, Lhassane Ismaili, Carine Van Lint, Georges Herbein
Summary: In this study, several compounds were tested for their antiviral activity against coronaviruses, and one compound, FAD LIJ2P40, showed low cytotoxicity and significant reduction in viral titer of SARS-CoV-2, which opens up the possibility for further evaluation as a potential treatment for Covid-19.
SCIENTIFIC REPORTS
(2022)
Article
Biochemistry & Molecular Biology
Imen Dakhlaoui, Paul J. Bernard, Diana Pietrzak, Alexey Simakov, Maciej Maj, Bernard Refouvelet, Arnaud Beduneau, Raphael Cornu, Krzysztof Jozwiak, Fakher Chabchoub, Isabel Iriepa, Helene Martin, Jose Marco-Contelles, Lhassane Ismaili
Summary: Alzheimer's disease (AD) is a complex neurodegenerative disease without a cure, causing significant social and economic impact. Multitarget-directed ligands (MTDLs) may provide a promising therapeutic strategy for AD treatment. In this study, novel MTDLs were designed and synthesized using simple and cost-efficient methods, targeting calcium channel blockade, cholinesterase inhibition, and antioxidant activity. Two sulfonamide-dihydropyridine hybrids were identified to possess cholinesterase inhibition, calcium channel blockade, antioxidant capacity, and Nrf2-ARE activating effect, suggesting their potential for further investigation in AD therapy.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Physical
Omar Portilla-Zuniga, Oscar M. Bautista-Aguilera, Jose J. Martinez, Hugo Rojas, Mario A. Macias, Isabel Iriepa, Adrian Perez-Redondo, Angel Sathicq, Juan-Carlos Castillo, Gustavo P. Romanelli
Summary: The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 degrees C for 45 min resulted in N-substituted pyrroles in yields of 68-97%. CATAPAL 200, with its high percentage of Bronsted-Lewis acid sites (23%) and pore diameter (37.8 nm), promotes the formation of pyrrole ring by facilitating condensation and dehydration processes. This protocol offers simplicity, high yields, reduced reaction time, solvent-free conditions, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. Furthermore, CATAPAL 200 is inexpensive and readily available, making it a cost-effective option for chemical transformations. The catalyst can be reused for up to five cycles without significant loss of catalytic activity, making this protocol sustainable and advantageous compared to conventional methods.
Article
Pharmacology & Pharmacy
Paul J. Bernard, Djamila Bellili, Lhassane Ismaili
Summary: This article introduces the characteristics of Alzheimer's disease and the challenges in the development of therapeutic drugs, and proposes a polypharmacological approach based on calcium channel blockers as a feasible option.
EXPERT OPINION ON DRUG DISCOVERY
(2023)
Article
Biochemistry & Molecular Biology
Emelina R. Rodriguez-Ruiz, Raquel Herrero-Labrador, Ana P. Fernandez-Fernandez, Julia Serrano-Masa, Jose A. Martinez-Montero, Daniel Gonzalez-Nieto, Mayuri Hana-Vaish, Mohamed Benchekroun, Lhassane Ismaili, Jose Marco-Contelles, Ricardo Martinez-Murillo
Summary: We describe a compound called MBA121, which is a tacrine-ferulic acid hybrid designed for the treatment of Alzheimer's disease (AD). MBA121 shows good anti-aggregation properties, selective inhibition of butyrylcholinesterase, neuroprotection against toxic insults, and promising ADMET properties. In animal experiments, MBA121 significantly reduced learning deficits and Aβ plaque burden, demonstrating its potential as a therapeutic agent for AD.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Medicinal
Tim Keuler, Carina Lemke, Paul W. Elsinghorst, Isabel Iriepa, Mourad Chioua, Maria Angeles Martinez-Grau, Christopher D. Beadle, Tatiana Vetman, Francisco Lopez-Munoz, Timo Wille, Ulrike Bartz, Winnie Deuther-Conrad, Jose Marco-Contelles, Michael Guetschow
Summary: The multifactorial nature of Alzheimer's disease requires the development of drugs that can target different relevant pathways. In this study, we synthesized a series of tailored chromanones and identified compound 19 as a representative compound with balanced pharmacological properties. Compound 19 showed inhibitory activities against human acetyl- and butyrylcholinesterase, monoamine oxidase-B, and high affinity to sigma 1 and sigma 2 receptors.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Chemistry, Medicinal
Tim Keuler, Carina Lemke, Paul W. Elsinghorst, Isabel Iriepa, Mourad Chioua, Maria Angeles Martinez-Grau, Christopher D. Beadle, Tatiana Vetman, Francisco Lopez-Munoz, Timo Wille, Ulrike Bartz, Winnie Deuther-Conrad, Jose Marco-Contelles, Michael Gutschow
Summary: The multifactorial nature of Alzheimer's disease necessitates the development of agents that can target multiple relevant pathways. In this study, we synthesized a series of tailored chromanones and evaluated their biological activities. One representative compound (compound 19) was identified, which exhibited balanced pharmacological properties and showed inhibitory activities against acetylcholinesterase, butyrylcholinesterase, monoamine oxidase-B, and high affinity to sigma 1 and sigma 2 receptors. Our findings provide a framework for the development of chromanone-based multineurotarget agents.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
