Article
Biochemistry & Molecular Biology
Alexei Lukin, Kristina Komarova, Lyubov Vinogradova, Marine Dogonadze, Tatiana Vinogradova, Piotr Yablonsky, Alexander Kazantsev, Mikhail Krasavin
Summary: A small set of twelve nitrofuran carboxamide compounds were synthesized from a readily available 2,6-diazaspiro[3.4]octane building block, exploring diverse variants of the molecular periphery, including various azole substituents. The synthesized compounds were evaluated for their in vitro inhibitory activities against Mycobacterium tuberculosis H37Rv, and a highly potent antitubercular lead compound with a minimal inhibitory concentration of 0.016 μg/mL was identified.
Article
Chemistry, Multidisciplinary
Shotaro Shimo, Richiro Ushimaru, Alicia Engelbrecht, Mei Harada, Kazunori Miyamoto, Andreas Kulik, Masanobu Uchiyama, Leonard Kaysser, Ikuro Abe
Summary: This study demonstrates that BelK and HrmI enzymes catalyze the N-oxygenation of L-lysine to generate 6-nitronorleucine, which is then cyclized by BelL and HrmJ enzymes to form the nitrocyclopropane ring with stereochemistry found in natural products. The study also reveals the inversion and retention of the configuration at C4 during the BelL and HrmJ reactions, providing insight into the unique strategy for stereocontrolled cyclopropane synthesis in nature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Igor B. Krylov, Stanislav A. Paveliev, Alexander S. Budnikov, Oleg O. Segida, Valentina M. Merkulova, Vera A. Vil, Gennady I. Nikishin, Alexander O. Terent'ev
Summary: The reactivity of CH-acidic and structurally related enol-containing heterocycles towards N-oxyl radicals was investigated, showing high affinity between these substrates. Highly selective and efficient N-oxyl radical mediated C-O coupling of substituted barbituric or Meldrum's acids with N-hydroxy compounds was achieved using inexpensive manganese-containing salts as oxidants. Metal-free C-O coupling was demonstrated using diacetyliminoxyl as both the oxidant and the coupling partner.
SYNTHESIS-STUTTGART
(2022)
Article
Microbiology
Claudia Velazquez-Sanchez, Miguel Angel Vences-Guzman, Soledad Moreno, Raunel Tinoco-Valencia, Guadalupe Espin, Josefina Guzman, Diana X. Sahonero-Canavesi, Christian Sohlenkamp, Daniel Segura
Summary: The inactivation of PsrA in Azotobacter vinelandii reduces the synthesis and content of unsaturated fatty acids, resulting in decreased cell viability. This study demonstrates the important role of PsrA in the regulation of unsaturated fatty acid metabolism by positively regulating fabAB.
MICROBIOLOGICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Arnab K. Maity, Annah E. Kalb, Matthias Zeller, Christopher Uyeda
Summary: (NDI)Ni-2 catalysts promote cyclopropanation reactions of 1,3-dienes by coupling with (Me3Si)CHN2. Mechanistic studies and DFT models suggest an alternative reaction mechanism involving Ni-2 mediated coupling and N-2 extrusion for generating cyclopropane products, explaining the experimental observations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Microbiology
John E. Cronan, Tiit Luk
Summary: Cyclopropane fatty acid synthase catalyzes the conversion of cis double bonds in unsaturated fatty acyl chains of phospholipid bilayers to cyclopropane rings. This modification primarily occurs in the early stationary phase and is limited to phospholipid bilayers containing unsaturated fatty acyl chains.
MICROBIOLOGY AND MOLECULAR BIOLOGY REVIEWS
(2022)
Article
Chemistry, Medicinal
Claire Le Manach, Jean Dam, John G. Woodland, Gurminder Kaur, Lutete P. Khonde, Christel Brunschwig, Mathew Njoroge, Kathryn J. Wicht, Andre Horatscheck, Tanya Paquet, Grant A. Boyle, Liezl Gibhard, Dale Taylor, Nina Lawrence, Tomas Yeo, Sachel Mok, Richard T. Eastman, Dorjbal Dorjsuren, Daniel C. Talley, Hui Guo, Anton Simeonov, Janette Reader, Mariette van der Watt, Erica Erlank, Nelius Venter, Jacek W. Zawada, Ayesha Aswat, Luisa Nardini, Theresa L. Coetzer, Sonja B. Lauterbach, Belinda C. Bezuidenhout, Anjo Theron, Dalu Mancama, Lizette L. Koekemoer, Lyn-Marie Birkholtz, Sergio Wittlin, Michael Delves, Sabine Ottilie, Elizabeth A. Winzeler, Thomas W. von Geldern, Dennis Smith, David A. Fidock, Leslie J. Street, Gregory S. Basarab, James Duffy, Kelly Chibale
Summary: A novel series of compounds was identified from a high-throughput screening campaign against Plasmodium falciparum, showing activity against multiple stages of the parasite lifecycle and providing a promising starting point for medicinal chemistry optimization and biological profiling. Further studies revealed compounds with low nanomolar asexual blood-stage activity and strong gametocyte sterilizing properties, which translated to transmission-blocking activity in standard assays. Mechanistic studies suggested the involvement of the P. falciparum cyclic amine resistance locus in resistance development.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Physical
Sung Kwon, Shawn Sandhu, Moaid Shaik, Jacob Stamm, Jesse Sandhu, Rituparna Das, Caitlin V. Hetherington, Benjamin G. Levine, Marcos Dantus
Summary: This study examines the possibility of three hydrogen atoms in one plane of the cyclopropane dication forming H-3(+) through a concerted ring-closing mechanism. Ultrafast strong-field ionization and disruptive probing measurements suggest that the formation time of H-3(+) is 249 +/- 16 fs, which is not consistent with a concerted mechanism but indicates a ring-opening process. Measurements on propene, an isomer of cyclopropane, show a similar formation time of H-3(+). Ab initio molecular dynamics simulations and a common potential energy surface support the ring-opening mechanism.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Engineering, Chemical
Jinpei Huang, Xingwei Lu, Xuejing Zhang, Yiqiang Jin, Yifeng Zhou
Summary: This paper investigates the microreaction preparation method of 1-oxa-2-azaspiro [2.5] octane. The results show that precise control of droplet dispersion, temperature, reaction time, and phase separation is crucial for process intensification. The microreaction system can achieve a higher product concentration compared to batch technology, making it a more efficient continuous-flow synthesis method.
CHINESE JOURNAL OF CHEMICAL ENGINEERING
(2023)
Article
Microbiology
Constantin Hays, Clara Lambert, Sophie Brinster, Gilles Lamberet, Laurence du Merle, Karine Gloux, Alexandra Gruss, Claire Poyart, Agnes Fouet
Summary: Enterococcus faecalis, a multiple antibiotic-resistant bacterium, has been characterized for its strategies in endogenous fatty acid synthesis, revealing that the FASII pathway is repressed by exogenous fatty acids while cyclopropanation enzyme deletion did not affect growth but resulted in bacteria lacking cyclic fatty acids. These findings indicate that neither FASII nor cyclopropanation enzymes are suitable antibiotic targets for E. faecalis.
JOURNAL OF BACTERIOLOGY
(2021)
Article
Biotechnology & Applied Microbiology
Sion Ham, Do-Hyun Cho, Suk Jin Oh, Jeong Hyeon Hwang, Hyun Jin Kim, Nara Shin, Jungoh Ahn, Kwon-Young Choi, Shashi Kant Bhatia, Yung-Hun Yang
Summary: In this study, recombinant Escherichia coli carrying both an indigo-producing plasmid and a cyclopropane fatty acid (CFA)-regulating plasmid were used to produce eco-friendly indigo dye. After optimizing the culture conditions, the strain with the CFA plasmid showed a 1.5-fold increase in indigo production compared to the control strain without the CFA plasmid after 24 hours of culture.
JOURNAL OF BIOTECHNOLOGY
(2023)
Article
Chemistry, Organic
Jiru Shao, Qinyuan Luo, Hongyan Bi, Sunewang R. Wang
Summary: A convenient route to synthesize 3- and 5-ylidenebutenolides from readily available cis-2-acylcyclopropane-1-carboxylates is described. The synergistic activation of vicinal acceptors in cis isomers generates highly strained bicyclic oxocarbenium ion intermediates, while the corresponding trans isomers are inactive under the same conditions due to the difficulty in forming such intermediates.
Review
Chemistry, Organic
Madhvi, Divya Utreja, Shivali Sharma
Summary: This review focuses on the advancements in methods of synthesis of barbituric acid derivatives and their applications as antimicrobial agents. By presenting the progress in synthesis of various barbituric acid derivatives, this review will help future researchers to analyze previous studies and explore new compounds for the development of efficient antimicrobial drugs.
CURRENT ORGANIC SYNTHESIS
(2022)
Article
Chemistry, Organic
Vijayaragavan Elumalai, Jorn H. Hansen
Summary: The synthesis of novel 5,7-diaryl and diheteroaryl indoles via efficient double Suzuki-Miyaura coupling is achieved with a low catalyst loading of Pd(PPh3)4 and water as the solvent, providing high yields without the need for N-protecting groups. The method is also applicable to N-protected and 3-substituted indoles, offering a green and convenient arylation strategy for the benzenoid ring of indoles. The synthesized diarylindoles exhibit fluorescence.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Energy & Fuels
Takashi Ikeda, Yoshihiro Tsuruda, Hiroaki Watanabe, Ryoichi Kurose, Toshiaki Kitagawa
Summary: This study investigated soot formation in outwardly propagating iso-octane rich unstable cellular flames through numerical simulation. It found that flame instability led to the formation of a cellular flame structure and enhanced soot formation. Variations in flame stretch rate influenced temperature distribution, affecting soot surface growth.
Article
Chemistry, Organic
Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Fedor Ryzhkov, Varvara M. Kalashnikova, Viktor A. Korolev, Mikhail P. Egorov
Summary: In this study, a facile and efficient electrochemical method was used to synthesize functionalized unsymmetrical spiro(indole-3,4'-pyrano[3,2-b]pyranes) in an undivided cell using a multicomponent reaction in n-propanol solvent. Molecular docking analysis revealed that the synthesized compounds have the potential to be protein ligands with potential pharmacological activities.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Nikita A. Frolov, Anatoly N. Vereshchagin
Summary: This article summarizes recent scientific literature on intra- and intermolecular reactions leading to the formation of various piperidine derivatives. It also covers the pharmaceutical applications of synthetic and natural piperidines, as well as the latest scientific advances in the discovery and biological evaluation of potential drugs containing piperidine moiety. The review aims to assist both novice researchers and experienced scientists in the synthesis of biologically active piperidines.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Artem N. Fakhrutdinov, Michail N. Elinson
Summary: Multicomponent green methodologies play an important role in organic synthesis by efficiently synthesizing compounds using simple and environmentally friendly catalysts and solvents, without the need for complex purification procedures.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Michail N. Elinson, Oleg I. Maslov, Artem N. Fakhrutdinov
Summary: In this study, the green chemistry techniques of PASE and one-pot synthesis were applied to efficiently and quickly synthesize Chromeno[2,3-b]pyridines, substances demanded in medicinal and material chemistry. By extending the PASE approach with 'component economy' and involving the solvent as a reactant, O-substituted 5-alkoxy-5H-chromeno[2,3-b]pyridines were synthesized via a two-step transformation. Mechanistic studies aided in optimizing the reaction conditions for high yields (77-93%).
Article
Chemistry, Organic
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Kirill A. Karpenko, Fedor V. Ryzhkov, Mikhail P. Egorov
Summary: A general electrocatalytic cascade approach was used to synthesize medicinally relevant compounds, which is fast and efficient and avoids traditional purification processes. According to screening molecular docking data, these compounds have potential applications in various medical fields.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Organic
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Oleg I. Maslov, Michail N. Elinson
Summary: In this paper, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in dimethyl sulfoxide was studied. The reaction yielded 2,4-diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile with good yield. The previously unknown chromeno[2,3-b]pyridine derivative was characterized using various spectroscopy techniques.
Article
Biochemistry & Molecular Biology
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Michail N. Elinson, Anatoly N. Vereshchagin, Roman A. Novikov, Artem N. Fakhrutdinov
Summary: Some of the most important transformations in organic chemistry are rearrangement reactions, which increase synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions has been a hot topic in the chemistry community. In this work, the thermal rearrangement of 7,9-dihalogen-substituted 5-(2-hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines in DMSO was proposed. Previously unknown compounds were synthesized with high yields (90-99%) and their structures were confirmed using 2D-NMR spectroscopy.
Article
Chemistry, Multidisciplinary
Michail N. Elinson, Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Varvara M. Kalashnikova, Oleg I. Maslov
Summary: A new type of chemical one-pot Knoevenagel-Michael reaction was discovered, leading to the synthesis of substituted bispyrazolone cyclopropanes with excellent yields and stereoselectivity. This efficient and convenient process utilizes aldehydes and pyrazolin-5-one as starting materials and has potential applications in the biomedical field. The mild conditions and simple isolation procedure further enhance the attractiveness of this one-pot reaction.
MONATSHEFTE FUR CHEMIE
(2023)
Review
Chemistry, Multidisciplinary
F. V. Ryzhkov, Y. E. Ryzhkova, M. N. Elinson, M. P. Egorov
Summary: This review provides an overview of the methods for synthesizing cognitive enhancers used as drugs to improve cognitive abilities or restore mental health in patients with pathological conditions. It summarizes information about trials and effectiveness of cognitive enhancers. The review specifically focuses on synthetic routes to compounds acting on cholinergic receptors, particularly muscarinic and nicotinic receptor ligands.
RUSSIAN CHEMICAL BULLETIN
(2023)
Review
Chemistry, Medicinal
Evgeniya A. Saverina, Nikita A. Frolov, Olga A. Kamanina, Vyacheslav A. Arlyapov, Anatoly N. Vereshchagin, Valentine P. Ananikov
Summary: In the past, the focus was mainly on individual antibacterial activity, but now there is a shift towards affecting more complex cellular frameworks and using multiple strategies to combat biofilms at different stages. Quaternary ammonium compounds (QACs) play a key role in these treatments. This review summarizes the literature data on the effectiveness of using commercially available and newly synthesized QACs, as well as synergistic treatment techniques based on them. It also discusses the development and application of antimicrobial coatings to prevent biofilm formation on various surfaces.
ACS INFECTIOUS DISEASES
(2023)
Article
Chemistry, Organic
Yuliya E. E. Ryzhkova, Fedor V. V. Ryzhkov, Michail N. N. Elinson
Summary: In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis of triethylammonium 2-(3-hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate has been developed. The presented protocol includes an aldol reaction and the formation of an ammonium salt. Triethylamine is both a reactant and a catalyst in the process. The structure of the synthesized title compound has been established by H-1, C-13-NMR and IR spectroscopy, mass spectrometry, and elemental analysis.
Article
Microbiology
Nikolay N. Kartsev, Elena V. Detusheva, Olga V. Kalmantaeva, Olga V. Korobova, Vladimir N. Gerasimov, Tatiana I. Kombarova, Aleksander I. Borzilov, Nadezhda K. Fursova, Anatoly N. Vereshchagin, Edward A. Svetoch
Summary: We described the genetic background and characteristics of a new EAHEC O181:H4 strain that poses a potential threat to humans. The strain showed typical morphology and enzymatic properties, susceptibility to most antibiotics, and a high degree of biofilm formation. Furthermore, it demonstrated cytotoxicity towards Vero cells.
Article
Chemistry, Multidisciplinary
Yuliya E. Ryzhkova, Michail N. Elinson, Anatoly N. Vereshchagin, Kirill A. Karpenko, Fedor V. Ryzhkov, Ivan E. Ushakov, Mikhail P. Egorov
Summary: Electrochemical synthesis provides a mild and environmentally friendly approach to the synthesis of interesting and useful molecules. This research discovered a new electrocatalytic multicomponent transformation, which selectively produces substituted unsymmetrical spiropyranopyrimidines in high yields. Molecular docking data suggests that these synthesized compounds may have significant applications in various medical fields.
CHEMISTRY-SWITZERLAND
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
