Review
Biochemistry & Molecular Biology
Yuta Murai, Makoto Hashimoto
Summary: In the fields of materials science and medicinal chemistry, heteroaromatic derivatives are important in developing new devices and discovering drugs. (3-trifluoromethyl)phenyldiazirine (TPD) is a crucial chemical method for understanding biological processes. TPD has been widely used in materials science to create novel electric and polymer devices at a lower cost. The combination of heteroaromatics and (3-trifluoromethyl)diazirine is a promising option for creating better materials and understanding the mechanisms of bioactive heteroaromatic compounds. This review provides a comprehensive synthesis of (3-trifluoromethyl)diazirine-substituted heteroaromatics.
Article
Chemistry, Multidisciplinary
Alessandro Alcinesio, Idil Cazimoglu, Gabriella Raye Kimmerly, Vanessa Restrepo Schild, Ravinash Krishna Kumar, Hagan Bayley
Summary: The authors applied modular design to construct modular synthetic tissues, assembling different functional 3D-printed building blocks for storing and releasing reagents, performing logic operations, responding to magnetic fields, and encapsulating living cells. They successfully built synthetic tissues capable of transmitting electrical signals and assembled hybrid tissues composed of both synthetic modules and modules containing living cells. By incorporating mutant protein nanopores within the building blocks, they created modular synthetic tissues with electrical outputs modulated by chemical inputs.
ADVANCED FUNCTIONAL MATERIALS
(2022)
Article
Chemistry, Organic
Spencer O. Scholz, Jesse B. Kidd, Luca Capaldo, Niecia E. Flikweert, Rowan M. Littlefield, Tehshik P. Yoon
Summary: This study presents a photosensitized [2 + 2] cycloaddition reaction for the straightforward access to complex cyclobutane scaffolds. Mechanistic studies suggest an activation mode involving energy transfer to the styrenyl alkene rather than the vinyl boronate ester.
Review
Chemistry, Multidisciplinary
Viviana Maffeis, Lukas Heuberger, Anamarija Nikoletic, Cora-Ann Schoenenberger, Cornelia G. Palivan
Summary: This article reviews the exponential growth of research on artificial cells and organelles, highlighting their potential for advancing fundamental biological processes. It focuses on the construction of artificial cells using micro- and nanoscale polymer-based compartments, exploring their varied chemistry for customizable assembly. The review delves into the architecture, usage, functional aspects, and communication of artificial cells, shedding light on the development of sophisticated multifunctional systems.
Review
Chemistry, Organic
Amit Pal, Pinku Prasad Mondal, Fathima Niloofar, Basudev Sahoo
Summary: This review summarizes the recent strategies for thioester synthesis from a variety of readily available feedstocks in modern synthesis. It also highlights the significant advancements in using progenitors of odorous thiols and CO-surrogates, as well as the utilization of native free thiols and CO gas.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Maxime Gauthier, Philip Waeles, Frederic Coutrot
Summary: Cyclic interlocked molecules have unique restrained tridimensional structure, and preserving the mechanical bond can facilitate post-synthetic intramolecular cyclization. However, the chemical linkage between reactive sites in interlocked rotaxanes remains an underexploited route in post-synthetic reactions.
Article
Biochemistry & Molecular Biology
Lisa Schmidt, Danny Wagner, Martin Nieger, Stefan Brase
Summary: A series of C-3-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates using one-step synthesis. The reactivity of these compounds was investigated by various reactions, demonstrating the importance of stable alkyl triamino-benzene-tricarboxylates for achieving total N-alkylation. The molecular structures of the products were confirmed by X-ray analysis.
Review
Multidisciplinary Sciences
Mirja Md Mahamudul Hassan, Saikat Guria, Sayan Dey, Jaitri Das, Buddhadeb Chattopadhyay
Summary: Transition metal-catalyzed C-H bond activation and borylation is a powerful synthetic method for transforming organoboron compounds to various functional groups. Remote C-H borylation is more challenging than ortho-borylation due to the inaccessibility of the C-H bonds. Recent discoveries in catalyst/ligand design, such as steric effects and noncovalent interactions, have enabled remote C-H borylation and its application in natural product synthesis. Ir-catalyzed C-H borylation is currently predominant, but cobalt catalysts are also being explored for sustainable and cost-effective development.
Review
Chemistry, Organic
Oleksandr O. Grygorenko, Dmitriy M. Volochnyuk, Bohdan V. Vashchenko
Summary: Current medicinal chemistry heavily relies on the quality of building blocks, with an emergence of many novel (or well-overlooked) chemotypes for drug discovery. This includes adapting new synthetic methodologies, designing new bioisosteres, and paying attention to underrated structural motifs.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Diego Nunez-Villanueva, Christopher A. Hunter
Summary: The development of replication methods for synthetic information oligomers is crucial for directed evolution to explore new chemical space. This study achieved template-directed replication of triazole oligomers by utilizing a covalent primer and non-covalent binding of complementary building blocks. The efficiency of the templated reaction was found to be influenced by the number of H-bonds formed between the template and the building blocks. Increasing the strength of the non-covalent interaction between the template and the building blocks led to an accelerated reaction. The successful replication was achieved using a phosphine oxide 3-mer building block that formed three H-bonds with the template.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Biochemistry & Molecular Biology
Sisa Chalan-Gualan, Vida Castro, Ruth Oropeza, Margarita Suarez, Fernando Albericio, Hortensia Rodriguez
Summary: This review provides an up-to-date overview of 3,4-dihydro-2(1H)-pyridones (3,4-DHPo) and their derivatives, highlighting their nomenclature, synthesis, and biological activity as well as their significance as building blocks for other relevant structures. The review also discusses nonconventional synthesis methods and emphasizes the potential of 3,4-DHPo in green chemistry. The biological activities of 3,4-DHPo, including vasorelaxant, anti-HIV, antitumor, antibacterial, and antifungal activities, demonstrate its potential in medicinal chemistry.
Article
Chemistry, Organic
Keisuke Iwata, Yasunobu Egawa, Katsunori Yamanishi, Hayato Tsuji
Summary: The acid-induced intramolecular cyclization of 1,1-disubstituted 3-aryl-2,3-dibromoallylalcohols leads to the formation of 2,3-dibromo-1H-indene derivatives and tetrabromodihydro-s-indacenes. These multi-brominated compounds can serve as versatile building blocks for the synthesis of various indene and indacene derivatives. The synthesis of dialkylmethylene-bridged oligo(phenylenevinylene)s demonstrates the attractive photophysical properties of these compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Endri Karaj, Shaimaa H. Sindi, L. M. Viranga Tillekeratne
Summary: This article reviews two challenging tools in drug development: photoactivation and bioorthogonal ligation. By providing historical and theoretical backgrounds, synthetic routes, and comparative analyses of different tools, it assists decision making in probe design. The survey of recent literature reports also identifies the latest trends in the field.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hans-Juergen Federsel
Summary: Several factors, such as the specific structural motifs of interest, the ability to perform consistently on a larger scale, the need for novel synthetic methodologies, and the requirement for environmental concern, play a role in the decision process for adopting certain reactions for industrial applications.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Review
Engineering, Chemical
Luisa G. Cencha, Mariana Allasia, Ludmila Ronco, Gisela C. Luque, Matias L. Picchio, Roque J. Minari, Luis M. Gugliotta
Summary: The review article summarizes the progress achieved in the synthesis of hybrid protein/synthetic polymer nanoparticles, which have the potential for industrial applications. Despite available technical achievements and efficacy proofs, practical implementation still poses challenges and should be the focus of future research.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Jumpei Taguchi, Kota Kimura, Kazunobu Igawa, Katsuhiko Tomooka, Takamitsu Hosoya
Summary: The generation of 3-azidoarynes from o-iodoaryl triflate-type precursors was achieved using a silylmethyl Grignard reagent as the activator. The azido group controls the regioselectivity of the reaction and can be further transformed into different nitrogen-containing compounds.
Article
Pharmacology & Pharmacy
Takayoshi Nakaoka, Ken-ichi Kaneko, Satsuki Irie, Aya Mawatari, Ami Igesaka, Yuta Uetake, Hidenori Ochiai, Takashi Niwa, Emi Yamano, Yasuhiro Wada, Masaaki Tanaka, Kohei Kotani, Hideki Kawahata, Joji Kawabe, Yukio Miki, Hisashi Doi, Takamitsu Hosoya, Maeda Kazuya, Hiroyuki Kusuhara, Yuichi Sugiyama, Yasuyoshi Watanabe
Summary: Uptake and efflux transporters play crucial roles in drug disposition. PET imaging is a useful tool for directly assessing drug transporter activity. A synthetic method for [18F]PTV, a PET probe for hepatobiliary transport, was developed. Rifampicin pretreatment significantly inhibited hepatic concentration and biliary excretion of the probe and decreased hepatic uptake clearance and canalicular efflux clearance. These results demonstrate the usefulness of [18F]PTV for investigating hepatobiliary transporters in humans.
DRUG METABOLISM AND PHARMACOKINETICS
(2022)
Article
Chemistry, Medicinal
Yuka Miyazaki, Masaki Kikuchi, Koji Umezawa, Aurelie Descamps, Daichi Nakamura, Gaku Furuie, Tomoe Sumida, Kanako Saito, Ninako Kimura, Takashi Niwa, Yuto Sumida, Takashi Umehara, Takamitsu Hosoya, Isao Kii
Summary: The study investigates DYRK1A's folding intermediate-selective inhibition and introduces a novel small molecule inhibitor termed dp-FINDY, expanding chemical options for kinase inhibitor design.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Hinano Takemura, Gaku Orimoto, Akihiro Kobayashi, Takamitsu Hosoya, Suguru Yoshida
Summary: This study discloses assembling methods using 2-azidoacrylamides with a nucleophilic amino group. Divergent transformations of the amine-type trivalent platform resulted in a wide range of 2-azidoacrylamides involving a fluorosulfonyl group. Consecutive click conjugations, including triazole formation, thiol-ene-type 1,4-addition, and SuFEx reactions, efficiently assembled easily available simple modules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Akihiro Kobayashi, Tsubasa Matsuzawa, Takamitsu Hosoya, Suguru Yoshida
Summary: The interrupted Pummerer reaction of alkynyl sulfoxides with phenols is reported, leading to the efficient synthesis of various benz[b]furans through the unexplored electrophilic activation of the electron-deficient alkynyl sulfinyl group. Utilizing readily available alkynes, thiosulfonates, and phenols, we successfully prepared functionalized benz[b]furans.
Article
Chemistry, Multidisciplinary
Zhouen Zhang, Takashi Niwa, Kenji Watanabe, Takamitsu Hosoya
Summary: In this study, a two-phase radiosynthetic method for the ipso-C-11-cyanation of aryl fluorides was developed, using nickel-mediated C-F bond activation. A practical protocol was established that does not require a glovebox, making it applicable for general PET centers. This method enabled the efficient synthesis of diverse [C-11]aryl nitriles, including pharmaceutical drugs. Stoichiometric reactions and theoretical studies demonstrated the significant promotion effect of lithium chloride on the oxidative addition, facilitating rapid C-11-cyanation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Takashi Niwa, Tsuyoshi Tahara, Charles E. Chase, Francis G. Fang, Takayoshi Nakaoka, Satsuki Irie, Emi Hayashinaka, Yasuhiro Wada, Hidefumi Mukai, Kenkichi Masutomi, Yasuyoshi Watanabe, Yilong Cui, Takamitsu Hosoya
Summary: This study reports the successful 11C-radiolabeling of eribulin, an approved anticancer drug, which enables the quantitative measurement of eribulin migration into tumor tissue. The optimized synthetic method provides a reproducible way to produce [35-11C]eribulin with high radiochemical purity and molar activity. PET imaging using mice shows specific accumulation of [35-11C]eribulin in tumors without significant metabolic changes.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2023)
Article
Chemistry, Multidisciplinary
Suguru Yoshida
Summary: We have developed selective methods for single C-F transformations of aromatic trifluoromethyl compounds, enabling us to prepare a broad range of organofluorines from simple benzotrifluorides through C-F and C-Si transformations. These methods include allylation using trityl cations, thiolation and azidation catalyzed by Yb(OTf)(3), as well as chlorination using trityl chloride. The resulting fluorosilyl group in these transformations can undergo further reactions such as protonation, halogenation, and Hiyama cross-coupling with C-Si cleavage. Additionally, benzyl fluorides can be synthesized through LiAlH4-reduction of the resulting fluorosilanes and further C-F transformations.
Article
Psychiatry
Manon Dubol, Jana Immenschuh, My Jonasson, Kayo Takahashi, Takashi Niwa, Takamitsu Hosoya, Sara Roslin, Johan Wikstrom, Gunnar Antoni, Yasuyoshi Watanabe, Mark Lubberink, Anat Biegon, Inger Sundstrom-Poromaa, Erika Comasco
Summary: The study investigated the availability of aromatase in healthy women before and after nicotine exposure. The findings suggest that nicotine acutely decreases aromatase availability in the thalamic area, indicating a potential mechanism mediating the effects of nicotine on human behavior.
COMPREHENSIVE PSYCHIATRY
(2023)
Article
Chemistry, Organic
Shinya Tabata, Mai Minoshima, Akihiro Kobayashi, Takamitsu Hosoya, Suguru Yoshida
Summary: Migrative thioamination of aryne intermediates using o-iodoaryl triflates and sulfilimines leads to the formation of highly functionalized o-thioaminated diaryl sulfides. The ring expansion of cyclic sulfilimines enables the synthesis of eight- and nine-membered organosulfur compounds from dibenzothiophene- and thianthrene-type sulfilimines, respectively.
Article
Chemistry, Organic
Jumpei Taguchi, Takumi Okuyama, Satomi Tomita, Takashi Niwa, Takamitsu Hosoya
Summary: An efficient method for producing 3-triazenylarynes from ortho-iodoaryl triflate-type precursors has been developed. The resulting arynes exhibit high regioselectivity in reactions with various arynophiles due to the presence of the triazenyl group. The 3-triazenylaryne precursors can be used as intermediates for the synthesis of diverse multisubstituted aromatic compounds through the transformation of the remaining triazenyl group in the aryne adducts and triazenyl group-directed ortho-C-H functionalization.
Article
Chemistry, Organic
Keisuke Nakamura, Yukiko Kumagai, Akihiro Kobayashi, Minori Suzuki, Suguru Yoshida
Summary: A practical method for synthesizing sulfinate esters from aryl iodides is presented, involving the direct oxidation of thioesters obtained through copper-catalyzed C-S formation. This efficient synthesis enables the preparation of a wide range of sulfinate esters using readily available starting materials such as carboxylic acids and anilines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Koyo Numata, Shinya Tabata, Akihiro Kobayashi, Suguru Yoshida
Summary: An efficient synthetic method for multisubstituted naphthalenes has been revealed, involving the cycloaddition of 4-hydroxy-2-pyrones with aryne intermediates. Highly functionalized 2-pyrones were synthesized from 4-hydroxy-2-pyrones through a short synthetic route. The resulting 2-pyrones underwent smooth reactions with a variety of aryne intermediates, generated from o-silylaryl triflates. This led to the formation of multisubstituted naphthalenes via Diels-Alder reaction and subsequent decarboxylative aromatization. The aryne reaction of 2-pyrones also played a role in the synthesis of naphthalenes with 1,2,3-triazole moieties by combining with the triazole formation of 4-azido-2-pyrones.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kazuya Sugiyama, Yuki Sakata, Takashi Niwa, Suguru Yoshida, Takamitsu Hosoya
Summary: The iridium-catalyzed azide-thioalkyne cycloaddition proceeds faster with benzyl azide than with phenyl azide. Additionally, high azido-type selectivity is observed in other combinations of azides with different steric environments. This discovery enables efficient assembly of three azidophilic molecules to triazido platforms through three sequential triazole-forming reactions.
CHEMICAL COMMUNICATIONS
(2022)