Article
Chemistry, Organic
Yongzhuo Xu, Boqiang Wang, Jiajia Wang, Xuan Zhou, Jiaxing Chen, Xinjia Guo, Guo-Jun Deng, Wen Shao
Summary: In this study, a simple method for the synthesis of 2-azidoimines through azidoamination reactions was reported. The synthetic potential of the method was further demonstrated through sequential condensation/amination reactions and chemoselective, orthogonal transformations, leading to the access of biologically active unsymmetrical diamines.
Article
Chemistry, Inorganic & Nuclear
Erica N. Faria, Andrew R. Jupp, Jose M. Goicoechea
Summary: In this study, N-functionalised phosphinecarboxamides were synthesized by reacting the 2-phosphaethynolate anion with different diamines. The resulting neutral compounds can be deprotonated to form phosphide anions, which can further react with electrophiles to produce secondary phosphines.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Dawid J. Kucharski, Rafal Kowalczyk, Przemyslaw J. Boratynski
Summary: Novel 1,2-diamines based on the mefloquine scaffold were prepared, with the most effective 11-aminomefloquine obtained through conversion of the 11-alcohol and subsequent alkylation. The substitution reactions mostly retained the configuration, and enantiomerically pure products were obtained through resolution. The efficacy evaluation of the obtained vicinal diamines showed that erythro-11-aminomefloquine is a superior catalyst in asymmetric transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Materials Science, Ceramics
Mitsuhiro Ishida, Yutaro Sashiyama, Hirofumi Akamatsu, Katsuro Hayashi, Kazuki Nakanishi, George Hasegawa
Summary: Porous polyimide (PI) monoliths were successfully synthesized from porous poly(amic acid) (PAA) xerogels by thermal imidization. The PAA xerogels exhibited low-density and good morphological stability, while the PI monoliths had higher porosity and flexibility. The porous PI thermal insulators demonstrated high temperature stability in air.
JOURNAL OF SOL-GEL SCIENCE AND TECHNOLOGY
(2022)
Article
Chemistry, Organic
Elpida Skolia, Mary K. Apostolopoulou, Nikolaos F. Nikitas, Christoforos G. Kokotos
Summary: An efficient, green, and metal-free photochemical protocol for synthesizing benzimidazoles has been developed using 2,2-dimethoxy-2-phenylacetophenone as a photoinitiator and CFL lamps as the light source. Good to high yields of the corresponding benzimidazoles were obtained, and mechanistic studies were conducted to determine the plausible reaction mechanism.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Khonzisizwe Somandi, Tswene D. Seanego, Tebogo Dlamini Nee Molatsane, Matthew Maree, Charles B. de Koning, Jarunee Vanichtanankul, Roonglawan Rattanajak, Thanaya Saeyang, Yongyuth Yuthavong, Sumalee Kamchonwongpaisan, Amanda L. Rousseau
Summary: A series of compounds were evaluated as potential inhibitors of Plasmodium falciparum dihydrofolate reductase (PfDHFR) and synthesized for in vitro inhibitory activity testing. The compounds showed promising inhibitory activity in the biochemical enzyme assay, but were less potent in the whole-cell assay. Further investigation into the pharmacokinetic properties of these compounds may lead to the development of more effective analogues.
Article
Biochemistry & Molecular Biology
Vladimir Burilov, Egor Makarov, Diana Mironova, Elza Sultanova, Islamiya Bilyukova, Kevser Akyol, Vladimir Evtugyn, Daut Islamov, Konstantin Usachev, Timur Mukhametzyanov, Svetlana Solovieva, Igor Antipin
Summary: This paper presents the synthesis of new water-soluble calixarene triazoles and investigates their aggregation behavior, as well as their binding and compaction abilities towards DNA. The results suggest that the tetradecyl-substituted calix[4]arene exhibits the best performance in terms of DNA binding and compaction.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Polymer Science
Dandan Li, Chengyang Wang, Xiaoying Yan, Shengqi Ma, Ran Lu, Guangtao Qian, Hongwei Zhou
Summary: Colorless polyimides were prepared using two novel diamines, and their structure-property relationship was systematically analyzed. The resulting polyimides exhibited excellent optical and thermal properties, making them potential candidates for optical and optoelectronic materials.
Review
Infectious Diseases
Michele Verboni, Diego Romano Perinelli, Alessandro Buono, Raffaella Campana, Maurizio Sisti, Andrea Duranti, Simone Lucarini
Summary: This report summarizes the synthetic methodologies, physicochemical properties, and biological activity of sugar fatty acid ester surfactants, emphasizing on 6-O-glucose, 6-O-mannose, 6-O-sucrose, and 6'-O-lactose ones. The study highlights the potential applications of glycolipids in pharmaceuticals, cosmetics, agriculture, and food production, providing valuable information for future research and innovative uses of this class of amphiphilic compounds.
Article
Biochemical Research Methods
Emelia Ansu-Gyeabourh, Enoch Amoah, Chandrashekar Ganesa, Abraham K. Badu-Tawiah
Summary: The monoacylation of symmetrical diamine was achieved by diluting primary α,ω-diamines in ethyl acetate and electrospraying the resulting mixture in ambient air towards a mass spectrometer. The N-acylated product formed in charged microdroplets without the need for acidifying and activating agents or heat. The study provided insight into the activation of esters to react with amines at the droplet surface due to the high abundance of protons at the air-droplet interface.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2021)
Review
Chemistry, Medicinal
Muhammad Syafiq Bin Shahari, Anton V. Dolzhenko
Summary: N-2,6-substituted 1,3,5-triazine-2,4-diamines (N-2-substituted guanamines) are a diverse scaffold with potential in the development of bioactive molecules. They can be used to construct compounds targeting various enzymes, receptors, transporters, and nucleic acids, with therapeutic applications in cancer, inflammation, and CNS disorders.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Diana Mironova, Egor Makarov, Islamiya Bilyukova, Kevser Akyol, Elsa Sultanova, Vladimir Evtugyn, Damir Davletshin, Elvina Gilyazova, Emil Bulatov, Vladimir Burilov, Svetlana Solovieva, Igor Antipin
Summary: The study focuses on investigating the aggregation and complexing properties of calixarenes as potential DNA condensation agents for gene delivery. Triazole derivatives of calix[4]arenes 7 and 8 containing monoammonium fragments were synthesized and characterized. The interactions between these compounds and calf thymus DNA were studied, and the cytotoxic properties against cancerous cells were evaluated. Compound 4 showed the highest toxic effect on MCF7 breast adenocarcinoma.
Article
Chemistry, Multidisciplinary
David T. J. Morris, Steven M. Wales, Javier Echavarren, Matej Zabka, Giulia Marsico, John W. Ward, Natalie E. Pridmore, Jonathan Clayden
Summary: Cyclic triureas derived from TACN were synthesized and characterized. Dynamic cyclochirality was observed, with the hydrogen-bonded urea groups exchanging enantiomers through bowl inversion and directionality reversal. Structural modifications were found to affect the enantiomerization barrier, resulting in a planar-chiral, atropisomeric bowl-shaped structure with high stereochemical stability solely from its hydrogen-bonding network.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Nanoscience & Nanotechnology
Wenwen Li, Yanyan Zhou, Ting Gao, Jingya Li, Sen Yin, Wenru Huang, Yuying Li, Qing Ma, Zhiwei Yao, Pengfei Yan, Hongfeng Li
Summary: The paper presents a chiral tetrahedron Eu4(LR)4 with circularly polarized luminescence (CPL) that can selectively detect chiral diamines. By recording the CPL intensities of the Eu3+ ion at 591 nm, the enantiomeric composition and concentration of chiral diamines can be simultaneously determined. The variations in CPL intensity depend on the configuration around the Eu3+ ion, while the turn-on response is due to the raising of the T1 state of the ligand.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Omar Alami, Regis Laurent, Marine Tasse, Yannick Coppel, Jerome Bignon, Said El Kazzouli, Jean-Pierre Majoral, Nabil El Brahmi, Anne-Marie Caminade
Summary: In this study, two families of phosphorhydrazone dendrons were synthesized and characterized. These dendrons were then grafted onto graphene oxide (GO) via click reaction. The resulting materials were tested for their biological properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Kate Lauder, Daniele Castagnolo
Article
Chemistry, Medicinal
Meir Touitou, Fabrizio Manetti, Camila Maringolo Ribeiro, Fernando Rogerio Pavan, Nicolo Scalacci, Katarina Zrebna, Neelu Begum, Dorothy Semenya, Antima Gupta, Sanjib Bhakta, Timothy D. McHugh, Hanoch Senderowitz, Melina Kyriazi, Daniele Castagnolo
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Multidisciplinary
Kate Lauder, Silvia Anselmi, James D. Finnigan, Yuyin Qi, Simon J. Charnock, Daniele Castagnolo
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Review
Biochemistry & Molecular Biology
Silvia Anselmi, Nandini Aggarwal, Thomas S. Moody, Daniele Castagnolo
Summary: Sulfoxides, important organic compounds widely used in pharmaceutical and organic chemistry, can be synthesized enantioenriched through various biocatalytic approaches. Recent advances include the use of reductive enzymes and unconventional solvents, such as ionic liquids and deep eutectic solvents, for greener and more sustainable synthetic pathways.
Article
Chemistry, Medicinal
Anita Toscani, Charlotte Hind, Melanie Clifford, Seong-Heun Kim, Antonia Gucic, Charlotte Woolley, Naima Saeed, Khondaker Miraz Rahman, J. Mark Sutton, Daniele Castagnolo
Summary: The study reports the synthesis and biological evaluation of a series of phenanthroline-based visible-light-activated manganese(I) carbon-monoxide-releasing molecules (PhotoCORMs) against ESKAPE bacteria and bacterial biofilms. These PhotoCORMs release CO under blue light irradiation and show effective antibacterial activity against multidrug-resistant bacteria, with potential applications in combating antimicrobial resistance.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Medicinal
Seong-Heun Kim, Dorothy Semenya, Daniele Castagnolo
Summary: Compounds with guanidine moieties have been utilized in designing novel drugs for various diseases due to their hydrogen-bonding capability and protonatability. This review focuses on recent advances in studying antimicrobial guanidine-containing compounds, emphasizing their structural diversity and pharmacological relevance.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Anita Toscani, Rossana Denaro, Sergio Fernando Castillo Pacheco, Matteo Biolatti, Silvia Anselmi, Valentina Dell'Oste, Daniele Castagnolo
Summary: A series of amidinourea compounds have been synthesized as potential non-nucleoside anti-HSV agents, showing micromolar activity against HSV-1 with low cytotoxicity. These compounds act in an early stage of the HSV replication cycle, just after viral attachment and entry.
Article
Chemistry, Medicinal
Dorothy Semenya, Meir Touitou, Camila Maringolo Ribeiro, Fernando Rogerio Pavan, Luca Pisano, Vinayak Singh, Kelly Chibale, Georg Bano, Anita Toscani, Fabrizio Manetti, Beatrice Gianibbi, Daniele Castagnolo
Summary: A series of indolyl-3-methyleneamines were designed and synthesized for investigation as new chemical entities against Mycobacterium tuberculosis (Mtb). Compound 7j displayed potent activity and may inhibit Mtb through a unique mechanism.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Fei Zhao, Kate Lauder, Siyu Liu, James D. Finnigan, Simon B. R. Charnock, Simon J. Charnock, Daniele Castagnolo
Summary: This study describes the development of novel biocatalytic and chemoenzymatic methods for the enantioselective synthesis of chiral beta-hydroxysulfides using ketoreductase enzymes. Four ketoreductases were discovered and isolated, enabling the synthesis of beta-hydroxysulfides with different configurations. By utilizing novel chemoenzymatic and biocatalytic reactions or dynamic kinetic resolution, high enantioselective synthesis was achieved using commercially available starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Medicinal
Guilherme F. S. Fernandes, Andrew M. Thompson, Daniele Castagnolo, William A. Denny, Jean L. Dos Santos
Summary: Tuberculosis (TB) has taken more lives than any other infectious disease in the past 2000 years. Despite the comparable death toll with COVID-19 in 2020, the World Health Organization emphasizes the need for new TB drugs to end this pandemic. However, only a small fraction of the promising anti-TB compounds reported annually successfully reach clinical development.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Dorothy Semenya, Meir Touitou, Domiziana Masci, Camila Maringolo Ribeiro, Fernando Rogerio Pavan, Guilherme Felipe Dos Santos Fernandes, Beatrice Gianibbi, Fabrizio Manetti, Daniele Castagnolo
Summary: The exploration around the 2,5-dimethylpyrrole scaffold of antitubercular hit compound 1 has led to the discovery of new derivatives that are active against Mycobacterium tuberculosis and multidrug-resistant clinical isolates. Some of these derivatives showed promising cytotoxicity profiles and were effective in inhibiting the growth of intracellular mycobacteria.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Physical
Silvia Anselmi, Alexandra T. P. Carvalho, Angela Serrano-Sanchez, Jose L. Ortega-Roldan, Jill Caswell, Iman Omar, Gustavo Perez-Ortiz, Sarah M. Barry, Thomas S. Moody, Daniele Castagnolo
Summary: This study identifies selective and robust MsrA biocatalysts capable of efficiently catalyzing enantioselective reduction of various aromatic and aliphatic chiral sulfoxides at concentrations of 8-64 mM with high yields and excellent enantiomeric excess (up to 99%). Through rational mutagenesis design using in silico docking, molecular dynamics, and structural nuclear magnetic resonance (NMR) studies, a mutant enzyme MsrA33 was developed, which can catalyze the kinetic resolution of bulky sulfoxide substrates with non-methyl substituents on the sulfur atom with enantiomeric excess up to 99%, overcoming a significant limitation of current MsrA biocatalysts.
Article
Chemistry, Physical
Haoyue Xiang, Salvatore Ferla, Carmine Varricchio, Andrea Brancale, Nicola L. Brown, Gary W. Black, Nicholas J. Turner, Daniele Castagnolo
Summary: Two enzymatic strategies were developed to oxidize 1,2,3,4-tetrahydroquinolines (THQs) and N-cyclopropyl-N-alkylanilines into quinolines and 2-quinolones, respectively. Whole cells and monoamine oxidase (MAO-N) enzymes were used for the biotransformation of THQs, while horseradish peroxidase (HRP)-catalyzed annulation/aromatization reaction followed by Fe-mediated oxidation was employed for the conversion of N-cyclopropyl-N-alkylanilines into 2-quinolone compounds.
Review
Biochemistry & Molecular Biology
Guilherme Felipe Santos Fernandes, Caue Benito Scarim, Seong-Heun Kim, Jingyue Wu, Daniele Castagnolo
Summary: Oxazolidinone is a five-member heterocyclic ring with diverse applications in medicinal chemistry. Among the isomers, 2-oxazolidinone has been extensively explored and numerous analogues have been developed. Despite promising pharmacological applications in various therapeutic areas, most oxazolidinone derivatives have not progressed beyond the initial stages of drug development. This review highlights the efforts of medicinal chemists in exploring this scaffold and emphasizes its potential for medicinal chemistry.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Silvia Anselmi, Siyu Liu, Seong-Heun Kim, Sarah M. Barry, Thomas S. Moody, Daniele Castagnolo
Summary: A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed with CALB and AcOEt, leading to high yields and excellent E-factors in the synthesis of a range of sulfoxides, including the drug omeprazole.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
