Review
Chemistry, Organic
Quan Liu, Wenquan Wang, Meng Liu
Summary: This review discusses the single metal catalysis and synergistic catalysis of various catalyst systems for the synthesis of pyrrolo[1,2-a]quinoxaline. The catalytic mechanisms in different systems are thoroughly introduced and analyzed. The advantages and disadvantages of existing catalyst systems are evaluated, and the prospects of new catalysts and synthesis methods are presented.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Jimin Xu, Shuizhen Shi, Gang Liu, Xuping Xie, Jun Li, Andrew A. Bolinger, Haiying Chen, Wenbo Zhang, Pei-Yong Shi, Hua Liu, Jia Zhou
Summary: Novel pyrrolo[1,2-a]quinoxaline-based derivatives have been identified as potent and selective Sirt6 activators with low cytotoxicity. These compounds can repress inflammation and cancer cell formation, and also exhibit inhibitory effects on SARS-CoV-2 infection.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Subhro Mandal, Animesh Pramanik
Summary: Hydroxylated polycyclic pyrrolo/indolo[1,2-a]quinoxaline-fused lactam derivatives were obtained in high diastereoselectivity via PhI(OAc)(2)-mediated ring expansion and concurrent solvent insertion from spirofused quinoxalines. X-ray crystal structure analysis revealed that these polycyclic lactams are nonplanar molecules with one or two axially chiral biaryl or N-arylindolyl bridges and one chiral center at the bridgehead carbon.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Di Hao, Zhen Yang, Yali Liu, Yang Li, Yan Liu, Ping Liu
Summary: A copper-promoted direct C1-amination of pyrrolo[1,2-a]quinoxalines with N-fluorobenzenesulfonimide (NFSI) has been successfully achieved, leading to a diverse range of C1-aminated pyrrolo[1,2-a]quinoxalines with broad substrate scope and good functional group tolerance. The gram-scale synthesis and further derivation of the aminated product were also investigated. Mechanistic studies suggest the involvement of a free-radical process.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Biochemistry & Molecular Biology
Beatrice-Cristina Ivan, Stefania-Felicia Barbuceanu, Camelia Mia Hotnog, Octavian Tudorel Olaru, Adriana Iuliana Anghel, Robert Viorel Ancuceanu, Mirela Antonela Mihaila, Lorelei Irina Brasoveanu, Sergiu Shova, Constantin Draghici, George Mihai Nitulescu, Florea Dumitrascu
Summary: New pyrrolo[1,2-b]pyridazines were synthesized by cycloaddition reaction and evaluated for their cytotoxicity on plant cells, crustacean animal cells, and human adenocarcinoma-derived adherent cell lines. The compounds exhibited low toxicity on plant cells and showed toxic effects on crustacean animal cells to varying degrees. In vitro compound-mediated cytotoxicity assays demonstrated dose- and time-dependent cytotoxic activity for several compounds, with the highest anti-tumor activity observed against colon cancer cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Nataïlia M. Moreira, Ingrid T. de Miranda, Jhonathan R. N. dos Santos, Till Opatz, Glaucius Oliva, Rafael V. C. Guido, Arlene G. Correa
Summary: Reactions involving C(sp(3))-H bonds of azaarenes have been extensively studied for their ability to directly functionalize these N-heterocycles without harsh conditions. In this study, α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate were employed to functionalize 4-methylquinazolines and 1-benzylisoquinolines. Under optimized conditions, 21 pyrrolo[1,2-c]quinazolines, an imidazo[1,2-c]quinazoline, and 4 pyrrolo[2,1-a]isoquinolines were obtained in moderate to good yields. Furthermore, the biological activity of the pyrrolo[1,2-c]quinazolines against Plasmodium falciparum was evaluated and promising results were obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ameen Ali Abu-Hashem, Sami A. Al-Hussain, Magdi E. A. Zaki
Summary: In this study, a series of new polycyclic aromatic compounds were synthesized and evaluated for their anti-cancer activity. Some compounds showed significant cytotoxicity against various human cancer cell lines.
Article
Chemistry, Physical
Aniket Karpe, Aniket Parab, Gokul Ganesan, Pravin Walke, Atul Chaskar
Summary: This study reports two highly conjugated organic fluorophores that show rapid and selective detection of explosive molecules. Experimental and computational methods were used to determine the photophysical properties and detection limits of these molecules.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Patricia Sanchez-Alonso, Mercedes Griera, Javier Garcia-Marin, Manuel Rodriguez-Puyol, Ramon Alajarin, Juan J. Vaquero, Diego Rodriguez-Puyol
Summary: Novel compounds targeting PTP1B as potential therapeutics for diabetes and other diseases have been synthesized, showing inhibitory activity against the enzyme and potential insulin mimetic effects in cells.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Physical
Raviteja Chemboli, K. R. S. Prasad, Paritala Raghava Rao, A. V. D. Nagendra Kumar, Mandava Bhuvan Tej, Ravikumar Kapavarapu, M. V. Basaveswara Rao, Manojit Pal
Summary: A series of indolo[1,2-a]quinoxaline derivatives were synthesized via an ultrasound assisted MCR method, showing potential cytotoxic properties against cancer cell lines.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Medicinal
Javier Garcia-Marin, Mercedes Griera, Ramon Alajarin, Manuel Rodriguez-Puyol, Diego Rodriguez-Puyol, Juan J. Vaquero
Summary: In this study, a scaffold-hopping approach was developed to design new PTP1B inhibitors by modifying the pyrrole ring of the pyrrolo[1,2-a]quinoxaline core. Computational techniques were used to explain the molecular interaction with PTP1B and support the recognition mechanism of the inhibitors. The designed inhibitors showed promising results in cellulo models, validating this approach for drug design.
Article
Biochemistry & Molecular Biology
Sergii Demchenko, Roman Lesyk, Oleh Yadlovskyi, Johannes Zuegg, Alysha G. Elliott, Iryna Drapak, Yuliia Fedchenkova, Zinaida Suvorova, Anatolii Demchenko
Summary: A series of novel quaternary salts were synthesized, with most showing antimicrobial activity and one compound demonstrating broad spectrum activity against various bacteria and fungi, as well as high hemolytic activity against human red blood cells.
Article
Chemistry, Organic
Yan Long, Yun Wang, Yue-You Chen, Wen-Yong Han, Nan-Wei Wan, Wei-Cheng Yuan, Yong-Zheng Chen, Bao-Dong Cui
Summary: This article describes an inexpensive copper-catalyzed sequential reaction process for synthesizing structurally diverse spiro-dihydropmolo[1,2-a]quinoxaline derivatives. The significance of this method is highlighted by its ability to convert synthetic compounds into potentially bioactive molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ivain Velazco-Cabral, Juan Luis Vazquez, Yolanda Alcaraz-Contreras, Francisco Delgado, Eduardo Pena-Cabrera, Marco Garcia A. Revilla, Miguel A. Vazquez
Summary: A novel synthetic methodology using Fischer carbene complexes for (3+3) cyclization to form fluorescent pyrrolo[1,2-a]pyrimidines is reported. The selectivity of the reaction process was studied and the photophysical properties of the synthesized dyes were evaluated. The dyes showed absorption at wavelengths of 240-440 nm and emission at wavelengths of 470-513 nm, with high quantum yields and Stokes shifts ranging from 75-226 nm.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Taian Li, Mong-Feng Chiou, Yajun Li, Changqing Ye, Min Su, Mengyu Xue, Xiaobin Yuan, Chuanchuan Wang, Wen-Ming Wan, Daliang Li, Hongli Bao
Summary: Pyrroles are important heterocycles in pharmaceuticals and agrochemicals. This study presents a metal-free method for the synthesis of unsymmetrically tetrasubstituted NH-pyrroles using a consecutive chemoselective double cyanation. The desired pyrroles were obtained with high yields and good functional group tolerance. Additionally, pyrrolo[1,2-a]pyrimidines were synthesized as synthetic applications of NH-pyrroles, and these compounds showed unpredictable time-dependent aggregation-induced emission enhancement properties.
Article
Chemistry, Multidisciplinary
Philippe Guionneau, Mathieu Marchivie, Guillaume Chastanet
Summary: The concept of multiscale understanding of SCO emphasizes the importance of considering structure-property relationships at different physical scales to fully grasp and take advantage of the phenomenon. This approach expands the range of potential applications, including the development of shape memory materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Bruno Oyallon, Marie Brachet-Botineau, Cedric Loge, Thomas Robert, Stephane Bach, Sajida Ibrahim, William Raoul, Cecile Croix, Pascal Berthelot, Jean Guillon, Noel Pinaud, Fabrice Gouilleux, Marie-Claude Viaud-Massuard, Caroline Denevault-Sabourin
Summary: New quinoxaline derivatives acting as dual Pim1/2 inhibitors showed potent inhibition of Pim-1 and Pim-2 enzymes in vitro, and were able to inhibit the growth of multiple myeloma and colorectal carcinoma cell lines expressing high levels of Pim-1/2 kinases.
Article
Biochemistry & Molecular Biology
Justine Deborne, Noel Pinaud, Yannick Cremillieux
Summary: The study evaluated the potential of a miniaturized implantable NMR coil to acquire proton NMR spectra in sub-microliter regions of interest and to obtain metabolic information. Results showed that the designed implantable microcoil is suitable for in vivo MRS and can be used for probing the metabolism in localized and very small regions of interest in a tumor.
Article
Peripheral Vascular Disease
Pesque Raphaelle, Peyrilles Elodie, Jourdan Nathalie, Albert Odile, Sessink Paul, Madelaine Isabelle, Levert Helene
Summary: This study compared the risk of 5-fluorouracil (5-FU) contamination when nurses disconnect the infusion line of an elastomeric pump using different configurations. The use of the closed-system transfer device, Qimono(R), significantly reduced 5-FU contamination compared to the needle-free connector and standard Luer lock.
JOURNAL OF VASCULAR ACCESS
(2023)
Article
Biophysics
Justine Deborne, Noel Pinaud, Yannick Cremillieux
Summary: Miniaturized NMR receiver coils are effective for improving detection sensitivity in MRS and MRI studies, especially in small volumes or regions of interest. Implantable microcoils showed a sensitivity gain of over 50 compared to external coils, with diagnostic proton spectra obtained from brain regions as small as a few hundred nanoliters. The minimally invasive nature of the coil implantation process was highlighted, making these microcoils new tools for probing tissue metabolism.
NMR IN BIOMEDICINE
(2021)
Article
Chemistry, Organic
Jean Guillon, Solene Savrimoutou, Sandra Albenque-Rubio, Noel Pinaud, Stephane Moreau, Vanessa Desplat
Summary: A new substituted pyrroloquinoxaline compound was synthesized and its structure was characterized using various analytical techniques. This compound exhibited interesting cytotoxic potential against multiple human leukemia cell lines.
Article
Chemistry, Physical
Simon Garnier, Kevin Brugemann, Agnieszka Zak, Johnny Vercouillie, Marie Potier-Cartereau, Mathieu Marchivie, Sylvain Routier, Frederic Buron
Summary: The first access to N-1, N-4 disubstituted pyrrolo[2,3-d][1,2,3]triazoles is reported, and aryl groups were introduced at the C-5 and C-6 positions through regioselective electrophilic brominations followed by Suzuki-Miyaura cross coupling reactions.
Article
Radiology, Nuclear Medicine & Medical Imaging
Audrey Lavielle, Fabien Boux, Justine Deborne, Noel Pinaud, Sandrine Dufort, Camille Verry, Sylvie Grand, Irene Tropres, Clement Vecco-Garda, Geraldine Le Duc, Stephane Mornet, Yannick Cremillieux
Summary: This study aims to generate T1 maps from MR images using the MPRAGE sequence and evaluate its feasibility in phantoms, animal models, and patients with brain metastases. The results demonstrate that the MPRAGE sequence can be used as a method to measure the concentration of Gd-based theranostic agents within a standard clinical imaging protocol.
JOURNAL OF MAGNETIC RESONANCE IMAGING
(2023)
Article
Chemistry, Multidisciplinary
Ugo Serdan, Lucas Robin, Mathieu Marchivie, Mathieu Gonidec, Patrick Rosa, Elen Duverger-Nedellec, Emilie Pouget, Philippe Sainctavit, Marie-Anne Arrio, Amelie Juhin, Andrei Rogalev, Fabrice Wilhelm, Elizabeth A. A. Hillard
Summary: By integrating enantiomers into a conglomerate-forming matrix, we can control the formation of conglomerates. Ni(II) and Fe(II) form molecular alloys with Zn(II), with Ni(II) allowing for higher concentrations compared to Fe(II). Fast-growing precipitates are more likely to form chiral phases, while slow re-crystallizations favor racemic phases.
CHEMISTRY-SWITZERLAND
(2023)
Article
Chemistry, Physical
Hilaire Mba, Matthieu Picher, Nathalie Daro, Mathieu Marchivie, Philippe Guionneau, Guillaume Chastanet, Florian Banhart
Summary: Spin-crossover particles of [Fe(Htrz)2trz](BF4) with sizes of some hundred nanometers were studied by in situ electron microscopy. Despite their high radiation sensitivity, it was possible to analyze the particles by imaging and diffraction so that a detailed analysis of crystallographic defects in individual particles became possible. The presence of tilt boundaries, where the tilt axis is the direction of the polymer chains, was detected in each particle. The defect structure only changes after a high number of transformations between the low-spin and high-spin phases, which can be explained by the anisotropy of the atomic architecture within the crystals.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Organic
Jean Guillon, Solene Savrimoutou, Sandra Albenque-Rubio, Noel Pinaud, Nina Fillova, Stephane Moreau, Virginie Baylot, Vanessa Desplat
Summary: A new substituted pyrroloquinoxaline compound was designed, synthesized, and characterized in this study. The compound showed interesting cytotoxic potential against different human leukemia cell lines.
Article
Materials Science, Multidisciplinary
Liza El-Khoury, Nathalie Daro, Guillaume Chastanet, Patrick Rosa, Dominique Denux, Laetitia Etienne, Vincent Mazel, Michael Josse, Mathieu Marchivie
Summary: Cool-SPS sintering of spin crossover materials allows for the fabrication of molecular ceramics with high relative density and improved cooperativity.
MATERIALS ADVANCES
(2023)
Article
Chemistry, Inorganic & Nuclear
Narsimhulu Pittala, Emmelyne Cuza, Dawid Pinkowicz, Michal Magott, Mathieu Marchivie, Kamel Boukheddaden, Smail Triki
Summary: A new 1D coordination polymer has been synthesized and characterized. The magnetic and vibrational infrared data analysis reveals the contribution of two Fe-II active centers. Photomagnetic experiment shows that the dehydrated phase exhibits a photomagnetic response.
INORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Matthew G. Reeves, Elodie Tailleur, Peter A. Wood, Mathieu Marchivie, Guillaume Chastanet, Philippe Guionneau, Simon Parsons
Summary: Crystal packing energy calculations are used to analyze a family of spin crossover complexes, revealing a linear relationship between transition abruptness and changes in intermolecular interaction energy in the crystal structures. Abrupt transitions are associated with significant stabilising and destabilising changes in intermolecular interaction energies. Different classes of SCO complexes exhibit varying trends in relation to transition abruptness.
Article
Chemistry, Inorganic & Nuclear
Rangsiman Ketkaew, Yuthana Tantirungrotechai, Phimphaka Harding, Guillaume Chastanet, Philippe Guionneau, Mathieu Marchivie, David J. Harding
Summary: OctaDist is an interactive and visual program designed for determining structural distortion in octahedral coordination complexes. It calculates octahedral distortion parameters from standard structural files and offers additional tools for molecular analyses and visualization. The program emphasizes performance, flexibility, ease of use, and clear documentation, and it can be easily customized to include new algorithms or analytical tools.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Medicinal
Shuang Mei, Su Jiang, Yuting Wang, Han Jing, Peng Yang, Miao-Miao Niu, Jindong Li, Kai Yuan, Yan Zhang
Summary: This study identifies a dual-targeting peptide, AP-1, that effectively inhibits variants of concern (VOCs) of SARS-CoV-2 without impairing host cell viability. The findings suggest that AP-1 could be a promising broad-spectrum agent for treating emerging VOCs of SARS-CoV-2.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Hyeonjun Lee, Ju Yeon Lee, Hyunsoo Jang, Hye Young Cho, Minhee Kang, Sang Hyun Bae, Suin Kim, Eunji Kim, Jaebong Jang, Jin Young Kim, Young Ho Jeon
Summary: By using liquid chromatography-tandem mass spectrometry and nuclear magnetic resonance experiments, we identified new chemical moieties that bind to the target sites of the protein of interest, allowing for reversible binding and protein degradation. This method has the potential to expand the application of PROTAC technology.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Yingying Li, Xiyou Du, Xinru Kong, Yuelin Fang, Zhijing He, Dongzhu Liu, Hang Wu, Jianbo Ji, Xiaoye Yang, Lei Ye, Guangxi Zhai
Summary: This study proposes a novel nanoplatform based on the autophagy cascade to overcome the obstacles in chemo-immunotherapy. The platform combines chemotherapy and starvation therapy to initiate pro-death autophagy and enhance antigen presentation, while also remodeling the immunosuppressive tumor microenvironment. Furthermore, the study discovers a new therapeutic direction for the respiration inhibitor 3-bromopyruvic acid (3BP) in cancer treatment. Overall, this study offers an opportunity to improve antitumor efficacy and boost immune responses.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Bingsi Wang, Mingxu Ma, Yusen Dai, Pengfei Yu, Liang Ye, Wenyan Wang, Chunjie Sha, Huijie Yang, Yingjie Yang, Yunjing Zhu, Lin Dong, Shujuan Wei, Linlin Wang, Jingwei Tian, Hongbo Wang
Summary: Breast cancer is a common malignant tumor in women, and drug resistance remains a clinical challenge. In this study, a novel compound, G-5b, was developed with potent antagonistic and degradation activities comparable to the current drug fulvestrant. G-5b also showed improved stability and solubility. Mechanistically, G-5b engages the proteasome pathway to degrade ER, inhibiting the ER signaling pathway and inducing apoptosis and cell cycle arrest. In animal models, G-5b exhibited superior pharmacokinetics and pharmacodynamics properties. Overall, G-5b is a promising long-acting SERD worthy of further investigation and optimization.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Karoline B. Waitman, Larissa C. de Almeida, Marina C. Primi, Jorge A. E. G. Carlos, Claudia Ruiz, Thales Kronenberger, Stefan Laufer, Marcia Ines Goettert, Antti Poso, Sandra V. Vassiliades, Vinicius A. M. de Souza, Monica F. Z. J. Toledo, Neuza M. A. Hassimotto, Michael D. Cameron, Thomas D. Bannister, Leticia Costa-Lotufo, Joa o A. Machado-Neto, Mauricio T. Tavares, Roberto Parise-Filho
Summary: A series of hybrid inhibitors combining pharmacophores of known kinase inhibitors and benzohydroxamate HDAC inhibitors were synthesized and evaluated for their anticancer activity and pharmacokinetic properties. Compounds 4d-f exhibited promising cytotoxicity against hematological cells and moderate activity against solid tumor models. Compound 4d showed potent inhibition of multiple kinase targets and had stable interactions with HDAC and members of the JAK family. These compounds showed selective cytotoxicity with minimal effects on non-tumorigenic cells and favorable pharmacokinetic profiles.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Michal Sulik, Diana Fontinha, Dietmar Steverding, Szymon Sobczak, Michal Antoszczak, Miguel Prudencio, Adam Huczynski
Summary: This study describes the synthesis of the first-in-class ivermectin derivatives obtained through derivatization of the C13 position, along with the unexpected rearrangement of the macrolide ring. These derivatives show potential for antiparasitic activity and are important for the development of new antiparasitic agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Jun Liu, Qiu-Xian Chen, Wen-Fu Wu, Dong Wang, Si -Yu Zhao, Jia-Hao Li, Yi-Qun Chang, Shao-Gao Zeng, Jia-Yi Hu, Yu-Jie Li, Jia-Xin Du, Shu-Meng Jiao, Hai-Chuan Xiao, Qiang Zhang, Jun Xu, Jian-Fu Zhao, Hai -Bo Zhou, Yong-Heng Wang, Jian Zou, Ping-Hua Sun
Summary: A new anti-infective drug strategy has been discovered to attenuate virulence and modulate inflammation caused by drug-resistant Pseudomonas aeruginosa infections. Compound 5f inhibits biofilm formation, macrophage migration, and inflammatory response induced by P. aeruginosa, showing potential as a novel candidate against drug-resistant infections.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Liuzeng Chen, Ke Wang, Lingyun Wang, Wei Wang, Lifan Wang, Jia Li, Xiaohan Liu, Mengya Wang, Banfeng Ruan
Summary: In this study, a series of novel anti-inflammatory compounds were designed and synthesized based on the natural product pterostilbene skeleton. Among them, compound 8 showed the highest activity and exhibited its effects through inhibition of pro-inflammatory cytokines by blocking the NF-KB/MAPK signaling pathway. Compound 8 also demonstrated a good relieving effect on acute colitis in mice and showed good safety in acute toxicity experiments.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)
Article
Chemistry, Medicinal
Si-Min Liang, Gui-Bin Liang, Hui-Ling Wang, Hong Jiang, Xian-Li Ma, Jian-Hua Wei, Ri-Zhen Huang, Ye Zhang
Summary: A series of novel multi-target antitumor agents were designed, synthesized, and evaluated. Some compounds exhibited significant antitumor activity and one compound showed excellent efficacy, limited toxicity, and low resistance. Further mechanism studies revealed that the compound exerted antitumor effects through multiple pathways.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2024)