Article
Chemistry, Physical
Yanke Jiang, Qianqian Cao, Yuanqiang Wang, Min Feng, Shenzhen Kong
Summary: Photochromic diarylethene derivatives have promising applications in optoelectronic devices. The optical properties and thermal stability of these derivatives can be greatly influenced by heteroatom substitution of the aryl groups. The study explored a series of diarylethene derivatives with different heteroatoms and found that increasing atomic weights of the substituents could affect optical properties and thermal bistability. Diarylethene with Se substituent was predicted to have the best thermal bistability and comparable photochromic properties.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Gaomou Xu, Chao Shang, Liangliang Huang, Yingchun Liu
Summary: In this study, the photoelectronic properties of the GDY monolayer and its derivatives were investigated, and it was found that the bandgap of the GDY monolayer can be effectively modulated by methods such as doping, cutting, and defect involvement, without compromising carrier transport and light-absorbing capability. Some GDY derivatives exhibit semimetal and conductor properties, making them highly promising candidates for the design of novel photoelectronic devices.
JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS
(2022)
Article
Chemistry, Organic
Honglin Shang, Wenfa Zhou, Xingzhi Wu, Jinchong Xiao, Yinglin Song
Summary: A series of functionalized benzofuran derivatives were synthesized and characterized. Alkyl groups were introduced to enhance solubility. The photophysical properties were examined and the self-assembly behaviors were studied. Compound 3b showed promising potential as an optical limiting material.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Shannon Pecnard, Abdallah Hamze, Jerome Bignon, Bastien Prost, Alain Deroussent, Laura Gallego-Yerga, Rafael Pelaez, Ji Yeon Paik, Marc Diederich, Mouad Alami, Olivier Provot
Summary: In this study, various ligands related to Combretastatin A-4 and isoCombretastatin A-4 were designed, synthesized, and evaluated for their ability to inhibit tubulin polymerization. The lead compound 15d showed remarkable sub-nanomolar cytotoxicity against 9 human cancer cell lines, with an IC50 value below 1 nM.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Naglaa F. El-Sayed, Marwa El-Hussieny, Ewies F. Ewies, Mohamed F. El Shehry, Hanem M. Awad, Marwa A. Fouad
Summary: Microtubules and the mitotic spindle are crucial targets for cancer treatment, and benzofuran and indole derivatives were designed as tubulin polymerization inhibitors in this study. Compound 6a showed strong antiproliferative activity by inhibiting tubulin polymerization and disrupting mitotic spindle formation, leading to apoptosis of HepG2 cells. It fit properly at the colchicine binding site of tubulin, suggesting it as a promising anticancer candidate for liver and breast cell carcinoma treatment.
DRUG DEVELOPMENT RESEARCH
(2022)
Article
Chemistry, Organic
Lukas Fliegel, Jens Christoffers
Summary: Reacting beta-oxoesters with PIFA yields alpha-(iodophenyl) derivatives, which serve as starting materials for the preparation of [b] annulated benzofurane derivatives through copper-catalyzed C-O coupling reaction. The resulting scaffold shows great potential in medicinal chemistry and can be diversified to obtain various structurally different compounds.
Article
Chemistry, Inorganic & Nuclear
Hamid Saeidian, Seyed Mahdi Mortazavi Asadabad, Zohreh Mirjafary
Summary: This study obtained detailed structural, electronic, and spectral data of maltol derivatives using the DFT/B3LYP method and evaluated their antioxidant properties and complexation with metal ions.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Thaipparambil Aneeja, Sankaran Radhika, C. M. A. Afsina, Gopinathan Anilkumar
Summary: Mic expectant syntheses are a green, effective, quick, and convenient method for creating organic compounds. Benzofuran and indole, with their wide range of biological activities, play important roles in pharmaceuticals, pesticides, and other fields. This review summarizes recent advancements in microwave-assisted synthesis of benzofurans and indoles from 2012-2020.
Article
Biochemistry & Molecular Biology
Sodeeq Aderotimi Salami, Vincent J. Smith, Rui Werner Macedo Krause
Summary: Spirocyclic compounds, which are found in many active compounds, can be synthesized efficiently and yield high results through the Michael condensation of 3-dicyanomethylene-2H-indol-2-ones with isothiocyanate derivatives under aqueous and mechanochemical conditions. This novel protocol offers advantages such as solvent-free reactions, ambient temperature, short reaction times, experimental simplicity, and excellent yields, making it a suitable alternative to volatile organic solvents.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Oncology
Joviana Farhat, Lara Alzyoud, Mohammad Alwahsh, Basem Al-Omari
Summary: This review highlights the contribution of benzofuran derivatives as anticancer agents and analyzes the impact of chemical structure on their activity. Benzofuran derivatives have potential advantages in cancer treatment and also show pharmacological activities in other diseases.
Article
Chemistry, Organic
Alina Tirla, Kevin M. Wernke, Seth B. Herzon
Summary: The study found that oxazoles containing both 5-hydroxy and 4-carboxy substituents are unstable. Analysis revealed discrepancies in the oxazole region between synthetic intermediates and the isolates, suggesting that precolibactins 969 and 795a may not contain 5-hydroxyoxazole-4-carboxylic acid residues.
Article
Chemistry, Multidisciplinary
Shaomin Chen, Zhiyan Chen, Tianjian Zhang, Bo Zhao, Bo You, Minghao Li, Yanlong Gu
Summary: An efficient acid-catalyzed three-component cascade strategy was established to synthesize phenyl-substituted dihydrocyclohepta[b]indole carboxylate, which is a privileged scaffold. Another route to access tetrahydrocyclohepta[b]indoles was also discovered. These methods are practically attractive due to readily available materials, inexpensive metal-free catalysts, eco-friendly solvents, and divergent synthesis.
Article
Chemistry, Medicinal
Yixin Liu, Zhao Wu, Minxin Li, Hui Gao, Chunping Wan, Zewei Mao
Summary: A series of novel benzofuran derivatives linked to dipiperazine moiety were prepared and their in vitro anticancer activity against Hela and A549 was investigated. The results demonstrated that the benzofuran derivatives exhibited potent antitumor effects. Particularly, compounds 8c and 8d showed better antitumor activity against A549 (IC50 = 0.12 μM and 0.43 μM). Further mechanism study revealed that compound 8d could significantly induce cell apoptosis in A549 through FACs analysis.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Agriculture, Multidisciplinary
Fabio F. Brescia, Maximilian Koch, Raffael C. Wende, Peter R. Schreiner, Holger Zorn, Marco A. Fraatz
Summary: Among the aroma compounds formed by Cystostereum murrayi, highly potent bicyclic benzofuran derivatives are found. In addition to dill ethers, the fungus also produces two stereoisomers of a rare compound called dihydromenthofurolactones and a C3-unsaturated analogue. Analysis of reference standards allowed for the identification of the formed stereoisomers.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Zuzanna Rzepka, Ewa Bebenek, Elwira Chrobak, Dorota Wrzesniok
Summary: The synthesized new 28-indole-betulin derivatives showed promising anticancer activity, particularly against MCF-7 breast cancer cells, possibly through inducing apoptosis.
Article
Chemistry, Physical
Ailong Li, Shuang Kong, Chenxi Guo, Hideshi Ooka, Kiyohiro Adachi, Daisuke Hashizume, Qike Jiang, Hongxian Han, Jianping Xiao, Ryuhei Nakamura
Summary: Incorporating Mn into Co3O4 catalyst can significantly extend its lifetime in acidic environment while maintaining its activity, which is an important step towards the realization of noble-metal-free water electrolysers.
Article
Materials Science, Multidisciplinary
R. Yamada, J. Fujioka, M. Kawamura, S. Sakai, M. Hirayama, R. Arita, T. Okawa, D. Hashizume, T. Sato, F. Kagawa, R. Kurihara, M. Tokunaga, Y. Tokura
Summary: The interplay between electron correlation and topology of relativistic electrons is important in the research of quantum materials and emergent functions.
NPJ QUANTUM MATERIALS
(2022)
Article
Nanoscience & Nanotechnology
Jiachen Wang, Kenjiro Fukuda, Daishi Inoue, Daisuke Hashizume, Lulu Sun, Sixing Xiong, Tomoyuki Yokota, Takao Someya
Summary: Flexible, lightweight, and large-area solar cells provide new power supply opportunities in the renewable energy field. In this study, a strategy using a eutectic gallium-indium (EGaIn) top-cathode without an electron transport layer was developed, achieving a record power conversion efficiency (PCE) of 12.7% in fully solution-processed, flexible organic photovoltaics (OPVs).
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Nanoscience & Nanotechnology
Wei-Chih Wang, Kyohei Nakano, Daisuke Hashizume, Chain-Shu Hsu, Keisuke Tajima
Summary: This study investigates the effects of intramolecular interactions on spontaneous orientation polarization (SOP) in thin films by synthesizing different derivatives of TPBi. The results show that the introduction of ethyl groups enhances SOP in the films, with the p-substituted derivative exhibiting the best performance. The conformational change of the molecules is identified as the main factor underlying the SOP enhancement.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Shohei Kumagai, Takeru Koguma, Tatsuro Annaka, Chizuru Sawabe, Yukio Tani, Hiroki Sugiura, Tetsuya Watanabe, Daisuke Hashizume, Jun Takeya, Toshihiro Okamoto
Summary: Functionalization of pi-conjugated compounds is an important strategy for developing high-performance organic optoelectronic materials. In this study, the regioselective dibromination of a nitrogen-embedded perylene diimide analogue was achieved through palladium(II)-catalyzed oxidation and dicyanation. The resulting compound exhibited a deep lowest-unoccupied molecular orbital and good redox stability, leading to high electron mobility in transistors.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Multidisciplinary
Airi Kuroda, Naoko Fujita, Tomomi Horita, Kei Ota, Alfredo Rosas-Sanchez, Manabu Hoshino, Daisuke Hashizume, Tsukasa Matsuo
Summary: In this study, the reaction between the bulky EMind-based compound and pyridine N-oxide was investigated, resulting in the formation of different germanium compounds. The reaction mechanism was also explored.
Article
Chemistry, Multidisciplinary
Kentaro Tashiro, Toshiaki Takei, Alejandro M. Fracaroli, Hiroyoshi Ohtsu, Masaki Kawano, Daisuke Hashizume
Summary: The study found that an N-Fmoc and C-tBu-protected glutamate bearing a phenanthrene moiety could crystallize and form a gel, with different structures depending on its optical purity or solvent. Treatment of an enantiomeric mixture of the compound in acetonitrile resulted in a mixture of gel and supernatant, with enrichment of the major enantiomer in the gel. Additionally, a racemic mixture of the compound also provided a gel/supernatant mixture, with enrichment of either L or D form of the compound stochastically due to chiral symmetry breaking during gelation.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Takayuki Motoyama, Toshihiko Nogawa, Takeshi Shimizu, Makoto Kawatani, Takeshi Kashiwa, Choong-Soo Yun, Daisuke Hashizume, Hiroyuki Osada
Summary: Proteasome inhibitors with gamma-lactam structure have potential as anticancer drugs. In this study, TAS1 homologues from two fungi were found to be capable of biosynthesizing gamma-lactam compounds similar to actinomycete proteasome inhibitors. One of these compounds, taslactam C, displayed strong proteasome inhibitory activity. This finding highlights the importance of TAS1 and its homologues in fungal gamma-lactam compound biosynthesis.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Shunsuke Yanagi, Akihisa Matsumoto, Naoyuki Toriumi, Yusuke Tanaka, Kazunori Miyamoto, Atsuya Muranaka, Masanobu Uchiyama
Summary: In this study, two bench-stable BzTAPs with 18 pi- and 20 pi-electron structures were designed and synthesized. It was found that the NIR-inert BzTAP can be converted to the NIR-active form in the presence of mild reducing agents. This finding is significant for the development of activatable NIR probes in reductive environments.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Masahiro Hamura, Kohei Sugano, Ryo Matsukura, Kei Ota, Tsukasa Nakahodo, Daisuke Hashizume, Tsukasa Matsuo
Summary: The structures of arylthiolates were confirmed using X-ray diffraction analysis. Different substituents were found to have different solid-state structures, with bulky substituents forming monomeric structures. A salt metathesis reaction between one of the compounds and FeCl2 resulted in the formation of a three-coordinate anion.
Article
Chemistry, Inorganic & Nuclear
Diego A. Resendiz-Lara, Alfredo Rosas-Sanchez, Daisuke Hashizume, Jose E. Barquera-Lozada, R. Alfredo Toscano, Jose G. Lopez-Cortes, M. Carmen Ortega-Alfaro
Summary: A series of stable eta(4)-[Fe(CO)(3)] complexes (3a-f) were successfully synthesized through the reaction of eta(2)-[Fe(CO)(4)] complexes under mild carbonylation conditions. The reaction of 3a-f under thermal conditions unexpectedly resulted in the formation of a novel family of complexes (5a-f) through a metathesis-haptotropic rearrangement between the starting eta(4)-vinylketene iron(0) complex 3 and a eta(4)-vinylcarbene iron(0) complex trapped in situ after a reversible carbonylation process favored by the thermal conditions. An analysis of the electron density distribution of 5e using high-resolution X-ray diffraction data and DFT framework was performed to understand the electronic communication between the two iron fragments.
DALTON TRANSACTIONS
(2023)
Article
Nanoscience & Nanotechnology
Baocai Du, Kenjiro Fukuda, Tomoyuki Yokota, Daishi Inoue, Daisuke Hashizume, Sixing Xiong, Shinyoung Lee, Masahito Takakuwa, Lulu Sun, Jiachen Wang, Takao Someya
Summary: Insufficient interfacial adhesion is a common problem in multilayered devices, causing reliability issues. In flexible organic photovoltaics (OPVs), poor adhesion between layers can lead to degradation and failure under mechanical deformations. By using argon plasma treatment, we were able to increase the interfacial adhesion between the active layer and the MoOX hole transport layer by 58%, improving mechanical reliability. The treated active layer had a higher surface energy, contributing to the improved adhesion. The mechanically stabilized interface prolonged the lifespan of the flexible OPV device under mechanical stress.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Aufandra C. Wardhana, Akira Yamaguchi, Kiyohiro Adachi, Daisuke Hashizume, Masahiro Miyauchi
Summary: The titanium dioxide photocatalyst is only active under UV irradiation, but a new excitation pathway called interfacial charge transfer (IFCT) has been found to activate copper(II) oxide nanoclusters-loaded TiO2 powder (Cu(II)/TiO2) for organic decomposition under visible-light irradiation. A photoelectrochemical study showed that the Cu(II)/TiO2 electrode exhibited a cathodic photoresponse under both visible-light and UV irradiation, generating H-2 evolution on the electrode. This study demonstrates a direct interfacial excitation-induced cathodic photoresponse for water splitting without the need for a sacrificial agent, which can contribute to the development of visible-light-active photocathode materials for fuel production.
Article
Chemistry, Physical
Abhijit Sen, Valerii Bukhanko, Heeyoel Baek, Aya Ohno, Atsuya Muranaka, Yoichi M. A. Yamada
Summary: The amination of aryl chlorides was achieved using polymeric nickel and iridium catalysts under microwave and visible-light irradiation, with a high reaction efficiency and recyclability. This approach offers a wide range of substrate compatibility and can be used for the synthesis of biologically active molecules.
Article
Chemistry, Multidisciplinary
Ryoto Yura, Shohei Kumagai, Kiyohiro Adachi, Daisuke Hashizume, Toshihiro Okamoto, Yoshiyuki Nonoguchi
Summary: This study demonstrates that supramolecular salt-functionalized n-doped ladder-type conducting polymers exhibit excellent stability in the presence of dry air.
CHEMICAL COMMUNICATIONS
(2023)