Article
Chemistry, Organic
Alexey P. Krinochkin, Yaroslav K. Shtaitz, Aluru Rammohan, Ilya I. Butorin, Maria Savchuk, Igor A. Khalymbadzha, Dmitry S. Kopchuk, Pavel A. Slepukhin, Vsevolod V. Melekhin, Anna Shcheglova, Grigory Zyryanov, Oleg N. Chupakhin
Summary: An operationally simple and highly efficient one-pot method has been developed for the synthesis of pyridines appended with pyrazole via an NH linker. The synthesized compounds showed promising in silico activity against JAK1, SYK, and FAK1 kinases. In vitro testing demonstrated significant cytotoxicity of the most promising compound against A-172 and HepG2 cancer cell lines, with IC50 values below 50 μM. The in vitro anticancer activity correlates well with the predicted in silico data.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Trung-Anh Le, Yong Guo, Jun-Nian Zhou, Jiaqi Yan, Hongbo Zhang, Tan-Phat Huynh
Summary: A novel chemical functionalization of guar gum (GG) by benzoic acid (BA) has been reported, with the product characterized using various analysis techniques. The presence of conjugated BA on GG-BA with grafting density of 5.5% was confirmed, and showed good biocompatibility towards mouse embryonic fibroblasts (MEF) and human mammary epithelial cells (MCF-10A). GG-BA shows promising potential for the development of biomaterials like bioadhesives, hydrogels, and coacervates.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Chemistry, Organic
Jeremy Saiter, Thomas Guerin, Morgan Donnard, Armen Panossian, Gilles Hanquet, Frederic R. Leroux
Summary: Trifluoromethoxylation has attracted great attention in recent years due to the high interest in the OCF3 group for pharmaceutical and agrochemical applications. However, the existing methods often require the use of toxic, expensive, unstable F3CO- transfer reagents, which can generate undesired side-products. To address this issue, researchers have proposed a strategy involving the in-situ generation of gaseous fluorophosgene from triphosgene, its conversion by fluoride into the OCF3 anion, and the direct use of the latter in nucleophilic substitutions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Matuszczyk, Yu Jin Lee, Seongsoo Kang, Piotr J. Chmielewski, Joanna Cybinska, Dongho Kim, Marcin Stepien
Summary: A series of propeller-shaped donor-acceptor compounds were successfully synthesized via nucleophilic substitution reactions, showing efficient charge transfer especially between ortho-positioned donors and acceptors. This study is of significance for understanding the process of electron transfer.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Saad Touqeer, Laura Ielo, Margherita Miele, Ernst Urban, Wolfgang Holzer, Vittorio Pace
Summary: The methodology involves efficient nucleophilic substitution on the P-chlorine linkage, allowing for the direct transfer of different alpha-substituted methyllithium reagents to chlorinated phosphorous electrophiles to synthesize geminal P-containing methanes. Uniformly high yields are observed regardless of the specific nature of the carbanion employed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zhensheng You, Kosuke Higashida, Tomohiro Iwai, Masaya Sawamura
Summary: In this study, non-activated aryl fluorides were found to react with potassium diorganophosphinites through nucleophilic aromatic substitution to form tertiary phosphine oxides, with a mechanism involving nucleophile-dependent SNAr reaction pathways.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Applied
Raffaele Senatore, Monika Malik, Vittorio Pace
Summary: The recent renewed interest in monofluoromethylation chemistry has led to the identification of fluoroiodomethane as an effective CH2F-delivering agent. This versatile reagent simplifies the installation of the fluoromethyl group into organic skeletons using different chemical logics, and has found various applications in drug molecule synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Laura Santos, Florian Audet, Morgan Donnard, Armen Panossian, Jean-Pierre Vors, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: An efficient method for the synthesis of high-value N-polyfluoroalkyl anilines, primary polyfluoroalkylamines, and N,N-bis(polyfluoroalkyl) amines via N-polyfluoroalkylation of sulfonamides and phthalimide derivatives using sulfuryl fluoride (SO2F2) is reported. The in situ formation of polyfluoroalkyl fluorosulfonates from commercially available fluorinated alcohols and economical sulfuryl fluoride is advantageous in terms of environmental impact and cost. This general method allows for the polyfluoroalkylation of a variety of substrates, providing valuable building blocks for life science applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
David Leparfait, Feng Xiao, Delphine Coupri, Sabrina Gueulle, Florie Desriac, Aurelie Budin-Verneuil, Nicolas Verneuil, Axel Hartke, Emmanuel Pfund, Thierry Lequeux
Summary: Tri- and tetra-substituted alkenes, including fluoroalkenes, were obtained via selective ring-opening reaction of functionalized oxetanes. By introducing adenine nucleic base, alkenyl and fluoroalkenyl derivatives were synthesized as potential nucleoside mimics and evaluated for their activity against DltA enzyme.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Florian Audet, Morgan Donnard, Armen Panossian, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: Sulfuryl fluoride is a gas used as a fumigant, but it has also gained interest in organic synthesis due to its unique properties. It has been used for sulfur-fluoride exchange chemistry and as an efficient activator in classic organic synthesis, forming fluorosulfonates. Recent research has focused on metal-catalyzed transformations from aryl fluorosulfonates and nucleophilic substitution reactions on polyfluoroalkyl alcohols, highlighting the advantages of polyfluoroalkyl fluorosulfonates compared to alternative reagents.
Article
Biochemistry & Molecular Biology
Nane A. Avagyan, Pavel S. Lemport, Konstantin A. Lysenko, Alexey O. Gudovannyy, Vitaly A. Roznyatovsky, Valentine S. Petrov, Mikhail F. Vokuev, Yuri A. Ustynyuk, Valentine G. Nenajdenko
Summary: An efficient method for synthesizing diamides of 4,7-difluoro-1,10-phenanthroline-2,9-dicarboxylic acid was elaborated. The method involves direct nucleophilic substitution with 4,7-dichloro-1,10-phenanthroline precursors, resulting in high yields of difluoro derivatives. Four new fluorinated ligands were successfully prepared and their structures were confirmed using spectroscopic methods and X-ray data. Lanthanoid complexes were also synthesized to demonstrate the applicability of the new ligands, with their structures studied using solid-state (IR spectroscopy, X-ray diffraction) and solution-state (NMR spectroscopy) techniques.
Article
Biochemistry & Molecular Biology
Vasiliy M. Muzalevskiy, Zoia A. Sizova, Valentine G. Nenajdenko
Summary: In this study, a series of derivatives of 2-trifluoromethylindole were successfully synthesized through halogenation and base-catalyzed reactions, and the high synthetic utility of these compounds in reactions with various nucleophiles was demonstrated.
Article
Chemistry, Organic
Clayton P. Donald, Amy Boylan, Truong N. Nguyen, Po-An Chen, Jeremy A. May
Summary: The (IPr)GaCl3/AgSbF6, AgSbF6, and GaCl3 catalysts were found to efficiently catalyze the substitution of the hydroxyl group of secondary and tertiary propargylic alcohols with organoboronic acids via C-C bond formation, and GaCl3 catalyst effectively synthesized all-carbon quaternary propargylic centers. These catalysts demonstrated the ability to perform substitutions at carbons bearing alkyl substituents, a capability that was lacking in other systems. The study showed that highly hindered carbon stereocenters, including quaternary centers bearing doubly ortho-substituted aryl rings, could be accessed efficiently using this method.
Article
Chemistry, Multidisciplinary
Guanyu Zhang, Maodie Wang, Petia Bobadova-Parvanova, Frank R. Fronczek, Kevin M. Smith, M. Graca H. Vicente
Summary: The synthesis and reactivity of 3,8-dibromo-dodecafluoro-benzo-fused BOPHY 2 were reported in this study, with reactions involving various nucleophiles and Pd(0)-catalyzed cross-coupling reactions. The resulting perfluoro-BOPHY derivatives showed different reactivities under different conditions, indicating potential applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Leonard Bock, Stefanie K. Schultheiss, Simone Maschauer, Roman Lasch, Susanne Gradl, Olaf Prante, Samir Z. Zard, Markus R. Heinrich
Summary: The study found that the synthesis of 2-[F-18]trifluoromethylated indoles from chlorodifluoromethyl precursors proceeds under milder conditions compared to known metal-free nucleophilic exchange reactions with [F-18]fluoride on chlorodifluoro-methyl arenes, likely involving a favorable elimination-addition mechanism on the 2-methyl position of the indole. This single step labeling methodology nicely complements existing routes to 2-[F-18]trifluoromethylated indoles, given the increasing interest in F-18-labeled compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Yo Hiranoi, Miho Hatanaka, Koji Nakano
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Miho Hatanaka, Yuichi Hirai, Yuichi Kitagawa, Takayuki Nakanishi, Yasuchika Hasegawa, Keiji Morokuma
Article
Chemistry, Inorganic & Nuclear
Shuhei Ogata, Naoto Goto, Shoya Sakurai, Ayumi Ishii, Miho Hatanaka, Koushi Yoshihara, Ryota Tanabe, Kyosuke Kayano, Ryo Magaribuchi, Kenta Goto, Miki Hasegawa
DALTON TRANSACTIONS
(2018)
Article
Chemistry, Physical
Miho Hatanaka, Ayato Osawa, Tomonari Wakabayashi, Keiji Morokuma, Miki Hasegawa
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2018)
Article
Chemistry, Multidisciplinary
Miho Hatanaka, Tomonari Wakabayashi
JOURNAL OF COMPUTATIONAL CHEMISTRY
(2019)
Article
Chemistry, Physical
Aya Miyazaki, Miho Hatanaka
Article
Chemistry, Physical
Shigeki Gocho, Hajime Nakamura, Shu Kanno, Qi Gao, Takao Kobayashi, Taichi Inagaki, Miho Hatanaka
Summary: Ground and excited state calculations at key geometries are crucial for understanding photophysical properties. To compute these geometries on noisy intermediate-scale quantum devices, a strategy combining a chemistry-inspired spin-restricted ansatz and a new excited state calculation method called VQE/AC was proposed. The VQE/AC method does not require pre-determination of constraint weights and has the potential to describe smooth potential energy surfaces. Excited state calculations at the FC and CI geometries were performed on ethylene and phenol blue, and energy errors were found to be at most 2 kcal mol(-1) even on the ibm_kawasaki device.
NPJ COMPUTATIONAL MATERIALS
(2023)
Article
Chemistry, Physical
Taichi Inagaki, Miho Hatanaka, Shinji Saito
Summary: In this study, the intermolecular vibration and relaxation dynamics of a water film and a water droplet on a graphene surface were investigated using low-frequency Raman spectra calculated from molecular dynamics simulations. The results showed that the interfacial water systems exhibited weakened libration and enhanced intermolecular hydrogen bond stretching compared to bulk water, indicating softened orientation motion. The study also revealed slower collective polarizability relaxation in the water droplet, which was attributed to positive correlation between induced polarizabilities caused by structural fluctuations. The research demonstrated the revealing capability of low-frequency Raman spectroscopy on the anisotropic and finite effects of intermolecular dynamics in water films and droplets.
JOURNAL OF PHYSICAL CHEMISTRY B
(2023)
Article
Chemistry, Multidisciplinary
Araki Wakiuchi, Swarit Jasial, Shigehito Asano, Ryo Hashizume, Miho Hatanaka, Yu-ya Ohnishi, Takamitsu Matsubara, Hiroharu Ajiro, Tetsunori Sugawara, Mikiya Fujii, Tomoyuki Miyao
Summary: Fourier-transform infrared (FTIR) spectroscopy is used to detect the presence of functional groups and molecules in a mixed solution of organic molecules. A chemometrics approach is proposed to accurately predict the concentration of components in chemical reactions and can be interpreted by humans. The proposed method decomposes the spectrum into peaks with different widths using wavelet transform and builds a sparse linear regression model using the wavelet coefficients. The method shows better predictive ability compared to conventional methods in predicting monomer concentration in copolymerization reactions.
Article
Chemistry, Physical
Miho Hatanaka, Hiromoto Kato, Minami Sakai, Kosuke Kariya, Shunsuke Nakatani, Takayoshi Yoshimura, Taichi Inagaki
Summary: In this study, density functional theory (DFT) calculations and machine learning (ML) techniques were used to extract factors controlling the luminescence quantum yields (LQYs) of cyclometalated iridium(III) complexes. The nonradiative decay process of the complexes was found to be induced by the rotation of a single bond in one of the ligands, converting the six-coordinate structure to the five-coordinate structure. Based on this finding, a data set correlating energy differences between six- and five-coordinate triplet structures with LQYs was collected, and ML models were constructed to predict LQYs.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Multidisciplinary
Tomoya Inoue, Miho Hatanaka, Atsushi Nakajima
Summary: Elemental substitution and doping can optimize the properties of functional materials. B atom substitution in Al-n NCs enhances their oxidative reactivities and the position of B atom affects the geometric structure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Tomomi Yoshii, Saori Tsuzuki, Shunya Sakurai, Ryu Sakamoto, Julong Jiang, Miho Hatanaka, Akira Matsumoto, Keiji Maruoka
Article
Chemistry, Multidisciplinary
Ryo Kurosaki, Hironobu Hayashi, Mitsuharu Suzuki, Julong Jiang, Miho Hatanaka, Naoki Aratani, Hiroko Yamada
Article
Chemistry, Multidisciplinary
Naoki Hayakawa, Kazuya Sadamori, Shota Tsujimoto, Miho Hatanaka, Tomonari Wakabayashi, Tsukasa Matsuo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
