Article
Chemistry, Organic
Ekaterina A. Lystsova, Maksim V. Dmitriev, Andrey N. Maslivets, Ekaterina E. Khramtsova
Summary: A new synthetic approach to pyrrolobenzothiazoles is developed based on 1,4-thiazine ring contraction in 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones under the action of nucleophiles. The proposed approach works well with alkanols, benzylamine, and arylamines. The synthesized pyrrolobenzothiazole derivatives represent an interest to pharmaceutics for targeted cancer therapy development.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Feng Pan, Haohu Li, Xiaohua Wang, Liwen Luo, Yanfei Lin, Qingkai Yu, Wenlin Xie, Lianpeng Zhang
Summary: A general and convenient protocol for the visible light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols was developed. This method employs commercially available hydrochloric acid as a cheap promoter and air as a sustainable oxidant. The reaction conditions are tolerant towards many functional groups and produce sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones.
Article
Chemistry, Organic
Andrey V. V. Ivanov, Alexander S. S. Bobkov, Svetlana V. V. Martynovskaya, Arsalan B. B. Budaev, Nadezhda M. M. Vitkovskaya
Summary: The influence of substituents on the pyrrole ring and at the triple bond on the formation of fused pyrrolooxazines from 1H-pyrrol-2-ylmethanols and propargyl chlorides has been studied both theoretically and experimentally. Quantum-chemical calculations (CBS-Q//B3) were used to evaluate the energy characteristics of the reaction. A one-pot transition metal-free synthesis of substituted 3-methyl-1H-pyrrolo[2,1-c][1,4]oxazines in good yields has been achieved in the superbasic system NaOH/DMSO.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dan Yang, Ai-Jiao Yang, Yong Chen, Jian-Hua Xie, Qi-Lin Zhou
Summary: A ruthenium-catalyzed asymmetric hydrogenation method was developed for the synthesis of functionalized beta-aryl cyclohexanols, with high yields and enantioselectivity up to 99% ee.
Article
Chemistry, Organic
Liangliang Luo, Xiao-Pan Chen, Zhao-Feng Li, Yuan Zhou, You-Cai Xiao, Fen-Er Chen
Summary: The palladium-catalyzed aerobic oxidative cyclization of substituted 2-(1H-pyrrol-1-yl)phenols with isocyanides via an O-H/C-H insertion cascade provides a facile access to pyrrolo[2,1-c][1,4]benzoxazine derivatives in good to excellent yields under O2 atmosphere. This protocol is characterized by its mild reaction conditions, atom-economy, and broad functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Tai-Lin Chen, Anilkumar S. Patel, Vicky Jain, Ramajayam Kuppusamy, Yi-Wen Lin, Ming-Hon Hou, Tsann-Long Su, Te-Chang Lee
Summary: The design of hybrid molecules with antiangiogenic and DNA cross-linking activities showed potential broad-spectrum anticancer effects, with compound 19a being a promising candidate. Using a benzology approach to improve bioavailability, these hybrids could be formulated for intravenous and oral administration, indicating a helpful strategy for enhancing combination therapy efficacy.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Ekaterina A. Lystsova, Alexander S. Novikov, Maksim V. Dmitriev, Andrey N. Maslivets, Ekaterina E. Khramtsova
Summary: Acyl(imidoyl)ketenes can be used to synthesize diverse drug-like heterocycles. By utilizing the [4+2]-cyclodimerization of acyl(1,3-benzothiazol-2-yl)ketenes, a new synthetic approach to pharmaceutically interesting pyrido[2,1-b][1,3]benzothiazol-1-ones has been developed. Thermal analysis and computational studies revealed the suitability of 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones as a source of acyl(1,3-benzothiazol-2-yl)ketenes, and a novel mode of thermal transformation of [e]-fused 1H-pyrrole-2,3-diones was discovered. The synthesized pyrido[2,1-b][1,3]benzothiazol-1-ones are of interest due to their potential antiviral activity.
Article
Chemistry, Multidisciplinary
Jishun Quan, Dongping Zhang, Zhuo Zhang, Jian Wang, Chao Ma, Maosheng Cheng
Summary: Compound B16 showed excellent neuroprotective activity and potential as a candidate for neuroprotection by attenuating NR2B expression induced by NMDA. It demonstrated good blood-brain barrier permeability and no false-positive activities, making it a promising compound for further research.
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
(2021)
Article
Biochemistry & Molecular Biology
Yanchun Li, Jishun Quan, Haoxuan Song, Dongzhu Li, Enlong Ma, Yanjuan Wang, Chao Ma
Summary: Selective inhibition of histone deacetylase 6 (HDAC6) has emerged as a promising approach for cancer treatment. In this study, a series of novel selective HDAC6 inhibitors were designed and synthesized using molecular hybridization, with compound A7 showing high potency and metastasis inhibitory effects in vitro, laying a foundation for further drug development.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuliang Wei, Simin Sun, Jiaxi Xu
Summary: A visible-light-induced direct and safe synthesis method for functionalized dimethyl 1-aryl-1,9a-dihydropyrido[2,1-c][1,4]thiazine-1-phosphonates has been developed. The reaction involves the generation of carbene from dimethyl (aryl(2-tosylhydrazono)methyl)phosphonates with cesium carbonate as base and the [1+5] annulation of carbenes with pyridinium 1,4-zwitterionic thiolates to produce functionalized 1,9a-dihydropyrido[2,1-c][1,4]thiazine derivatives. This method offers a safer alternative to the use of potentially dangerous phosphoryl diazo compounds and features simple, convenient, catalyst-free, and mild reaction conditions.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Zheng Luo, Huayou Hu, Chao Wang, Zhen Yang, Yefei Wang
Summary: Pyrrolo[2,1-a]isoquinoline derivatives were synthesized through a multistep reaction, using a specific catalytic system, under aerobic conditions.
Article
Chemistry, Multidisciplinary
Azam Barghi Lish, Alireza Foroumadi, Eskandar Kolvari, Fatemeh Safari
Summary: A facile synthetic method was used to obtain a series of compounds, which were structurally characterized and evaluated for their cytotoxic activities. One compound was found to have strong inhibitory effects on multiple cancer cells and can induce apoptosis.
Article
Chemistry, Medicinal
Sumi Lee, Dhulfiqar Ali Abed, Mai-Uyen Nguyen, Michael P. Verzi, Longqin Hu
Summary: The Keap1-Nrf2-ARE pathway is important in responding to oxidative stress. Small molecule inhibitors targeting the Keap1-Nrf2 protein-protein interaction (PPI) can be potential agents for chronic inflammatory diseases. Compound 12d with a 2-(4-fluorobenzyloxy) group was identified as the most potent inhibitor of Keap1-Nrf2 PPI. It showed increased mRNA levels of downstream genes through Nrf2 activation.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
N. A. Tretyakov, M. V. Dmitriev, A. N. Maslivets
Summary: 8-Aroyl-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-triones react with 6-aminopyrimidine-2,4(1H,3H)-diones to form 3-aroyl-4-hydroxy-1-(2-hydroxyalkyl)spiro(pyrrole-2,5'-pyrrolo[2,3-d]pyrimidine)-2',4',5,6'(1H,1'H,3'H,7'H)-tetraones. The structure of the products was confirmed by X-ray diffraction analysis.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
N. A. Tretyakov, M. Dmitriev, A. N. Maslivets
Summary: The reaction between 8-aroyl-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-triones and 2-sulfanylacetic acid yielded 2-{[3-aroyl-4-hydroxy-1-(2-hydroxyethyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl]sulfanyl}acetic acids, with their structures confirmed by X-ray analysis.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Engineering, Biomedical
Vanessa Sainz, Liane I. F. Moura, Carina Peres, Ana I. Matos, Ana S. Viana, Angela M. Wagner, Julia E. Vela Ramirez, Teresa S. Barata, Manuela Gaspar, Steve Brocchini, Mire Zloh, Nicholas A. Peppas, Ronit Satchi-Fainaro, Helena F. Florindo
ACTA BIOMATERIALIA
(2018)
Article
Chemistry, Medicinal
Ilija N. Cvijetic, Tatjana Z. Verbic, Pedro Ernesto de Resende, Paul Stapleton, Simon Gibbons, Ivan O. Juranic, Branko J. Drakulic, Mire Zloh
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Yujuan Zhang, Li Guo, Jinhu Huang, Yong Sun, Fang He, Mire Zloh, Liping Wang
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2019)
Article
Chemistry, Applied
Jiang-Er Lan, Xiao-Jin Li, Xiao-Feng Zhu, Zhong-Lin Sun, Jian-Ming He, Mire Zloh, Simon Gibbons, Qing Mu
Summary: This study identified five flavonoids from the traditional Chinese herb Artemisia rupestris L., which showed synergistic antibacterial effects against multidrug-resistant Staphylococcus aureus. Three of the compounds exhibited synergy when combined with norfloxacin against fluoroquinolone-resistant strains, and further investigations were conducted to explore the mechanisms of the synergistic effects.
NATURAL PRODUCT RESEARCH
(2021)
Article
Chemistry, Applied
Mazlina Mohd Said, Simon Gibbons, Anthony Moffat, Mire Zloh
JOURNAL OF NEAR INFRARED SPECTROSCOPY
(2019)
Review
Pharmacology & Pharmacy
Mire Zloh, Teresa S. Barata
EXPERT OPINION ON DRUG DISCOVERY
(2020)
Article
Biochemistry & Molecular Biology
Maja Vitorovic-Todorovic, Ilija Cvijetic, Mire Zloh, Andrej Perdih
Summary: Recently, we have successfully designed and synthesized a subnanomolar, reversible, dual-binding site acetylcholinesterase (AChE) inhibitor. Through six molecular dynamics simulations, we found that the crystal structure and the interactions between ligand functional groups and amino acid residues significantly affect the molecular recognition between AChE and its inhibitor. This study provides important structure-based data for the further optimization of reversible, dual binding AChE inhibitors.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2022)
Article
Biochemistry & Molecular Biology
Ilaria Passarini, Pedro Ernesto de Resende, Sarah Soares, Tadeh Tahmasi, Paul Stapleton, John Malkinson, Mire Zloh, Sharon Rossiter
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Biochemistry & Molecular Biology
Christina Wang, Sam Garlick, Mire Zloh
Summary: Antimicrobial resistance is a growing concern in healthcare, and antimicrobial peptides offer a promising route for developing new antibiotics, which can be designed successfully using deep learning techniques.
Article
Biochemistry & Molecular Biology
Charles Eldrid, Mire Zloh, Constantina Fotinou, Tamas Yelland, Lefan Yu, Filipa Mota, David L. Selwood, Snezana Djordjevic
Summary: Vascular endothelial growth factors (VEGFs) are essential regulators for blood and lymphatic vessels, interacting with neuropilins and tyrosine kinase receptors. The selectivity of neuropilins and VEGF receptors in binding to VEGF proteins affects their physiological roles. Studies have shown that conformational preferences of VEGF-derived peptides beyond the C-terminal arginine contribute to the ligand selectivity of neuropilins. These findings have implications for designing selective antagonists of neuropilin functions.
Article
Biochemistry & Molecular Biology
Mateusz Gosecki, Malgorzata Urbaniak, Nuno Martinho, Monika Gosecka, Mire Zloh
Summary: This study demonstrates the importance of molecular dynamics simulation in predicting the behavior of drug-polymer complexes and creating computationally derived binding mechanisms. Experimental validation of the simulated drug encapsulation and binding mechanisms highlight the value of molecular modeling in the development of drug delivery formulations.
Article
Materials Science, Biomaterials
Nuno Martinho, Rita F. Pires, Mire Zloh, Vasco D. B. Bonifacio
Summary: Polyurea (PURE) biodendrimers were evaluated as nanopolymers to prepare safe drug nanoformulations from mixtures containing genotoxic impurities, with (S)-ibuprofen (IBF) as the model drug. Computational molecular dynamics simulations showed that PURE nanoformulations are primarily driven by hydrogen bonding, electrostatic, and hydrophobic interactions.
JOURNAL OF MATERIALS CHEMISTRY B
(2021)
Article
Chemistry, Multidisciplinary
Helena Y. Yong, Gerald Larrouy-Maumus, Mire Zloh, Rosemary Smyth, Rayan Ataya, Christopher M. Benton, Michael R. Munday
Review
Chemistry, Medicinal
Mire Zloh
Review
Chemistry, Multidisciplinary
Liane I. F. Moura, Alessio Malfanti, Carina Peres, Ana I. Matos, Elise Guegain, Vanessa Sainz, Mire Zloh, Maria J. Vicent, Helena F. Florindo
MATERIALS HORIZONS
(2019)