Article
Biochemistry & Molecular Biology
Mehmet Esref Alkis, Kenan Buldurun, Nevin Turan, Yusuf Alan, Unzile Kelestemur Yilmaz, Asim Mantarci
Summary: In this study, a new Schiff base and its Ni(II) and Pd(II) complexes were synthesized and characterized. The antiproliferative activities of these compounds on liver cancer cells were evaluated, and it was found that the complexes exhibited stronger activity than the ligand. Electroporation was also shown to enhance the cytotoxicity of the complexes. These findings suggest that the Ni(II) and Pd(II) complexes have potential as anti-cancer agents, particularly in electrochemotherapy.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2022)
Article
Chemistry, Inorganic & Nuclear
Sara Realista, Paulo J. Costa, Luisa B. Maia, Maria Jose Calhorda, Paulo N. Martinho
Summary: Cyclic voltammetry and bulk electrolysis experiments showed that [Ni(ii)(salphen)] [1], [Ni(ii)(Bu-t-salphen)] [2], and a binuclear Ni(ii) compound combining salphen and Bu-t-salphen [3] can react with CO2 to generate a stable metal-carbonyl species under anaerobic conditions. When exposed to air, a stoichiometric amount of CO is released and protonation regenerates the initial complex. Through various spectroscopy studies and DFT calculations, it is proposed that the reduction of [Ni(i)(salphen)](-), (2)[1](-), leads to the formation of a CO2 complex, (2)[1(CO2)](-), which is further reduced to (3)[1(CO2)](2-). After protonation, the coordinated CO2 is reduced to CO and released, regenerating (1)[1]. The release of CO competes with CO2 in the second cycle, deactivating the system.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Alena Dmitrieva, Oleg A. Levitskiy, Yuri K. Grishin, Tatiana Magdesieva
Summary: A new oxidatively stable (S)-N-benzylproline-derived ligand and its Ni(II)-Schiff base complexes have been developed for targeted electrochemically induced oxidative modification of the amino acid side chain. The addition of a bulky tert-butyl group enhances the rigidity and stereoselectivity of the complexes, while also increasing reactivity towards electrophiles. The solubility of the ligand and its complexes is improved, allowing for easier scaling-up of the reaction procedure.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Olga Yu Vassilyeva, Elena A. Buvaylo, Vladimir N. Kokozay, Brian W. Skelton, Alexandre N. Sobolev, Alina Bienko, Andrew Ozarowski
Summary: Three new Ni-Zn heterometallic complexes were synthesized and structurally characterized, showing different exchange coupling behaviors and magnetic anisotropy. These complexes provide a new reference for the study of multinuclear complexes.
DALTON TRANSACTIONS
(2021)
Article
Biochemistry & Molecular Biology
Eyup Basaran, Hatice Gamze Sogukomerogullari, Resit Cakmak, Senem Akkoc, Tugba Taskin-Tok, Ayseguel Kose
Summary: Two chiral Schiff base ligands were synthesized and their corresponding metal complexes were prepared. The compounds were characterized by various analytical methods. The cytotoxic effects of these compounds on cancer cells and healthy cells were evaluated, and L1-Pd(II) was identified as a promising anticancer drug candidate. Molecular docking results revealed the interaction between L1-Pd(II) and colon cancer antigen protein.
BIOORGANIC CHEMISTRY
(2022)
Article
Materials Science, Multidisciplinary
Sultan Erkan, Duran Karakas
Summary: In this study, the Pt(B1)2, Pt(B2)2, and Pt(B3)2 complexes were modeled and their structures and property parameters were calculated. It was found that Pt(B3)2 exhibited higher NLO performance compared to the other complexes, and all complexes were suitable for the production of OLED materials. Additionally, it was suggested that Pt(B3)2 may have the highest solar cell performance.
MATERIALS TODAY COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
R. Reshma, R. Selwin Joseyphus, D. Arish, R. Jaya Reshmi Jaya, J. Johnson
Summary: A novel Schiff base was synthesized by condensation of imidazole-2-carboxaldehyde with l-histidine, which was then complexed with a series of 3-d metal(II) ions. The complexes exhibited excellent antibacterial and antifungal activities in vitro, with electronic spectra and magnetic moment data indicating an octahedral geometry for most complexes.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2022)
Article
Chemistry, Physical
Zohreh Alyaninezhad, Ahmadreza Bekhradnia, Reza Zibandeh Gorgi, Zahra Ghanbarimasir, Morteza Fouladpour
Summary: A series of novel metal complexes of 4-aminoantipyrine quinoxaline were synthesized and characterized. The synthesized compounds showed potential inhibitory activity in cancer cell lines.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Physical
Rupam Sen, Kingsukh Mondal, Antonio M. dos Santos, Livia B. L. Escobar, Paula Brandao, Mario S. Reis, Zhi Lin
Summary: A new chiral NaO2Ni4O2N2 cluster with a distorted capped cubane-type structure has been synthesized and its structure has been determined by single crystal X-ray diffraction. The complex exhibits a Ni4 cubane cluster with a sodium ion anchored on its face. The coordination geometries at each metal site show local distortions, which govern the magnetic anisotropy associated with each Ni II ion. The complex also showed good catalytic activity towards bromination of aromatic phenolic compounds, achieving up to 99% conversion with 100% selectivity to their corresponding bromo derivatives.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Pratikkumar Lakhani, Darshil Chodvadiya, Prafulla K. Jha, Vivek Kumar Gupta, Damian Trzybinski, Krzysztof Wozniak, Krzysztof Kurzydlowski, U. K. Goutam, Himanshu Srivastava, Chetan K. Modi
Summary: A Cu(ii)-salen complex encapsulated in MWW-framework was developed as an efficient chiral organocatalyst for synthesizing 3,4-dihydropyrimidin-2-(1H)-one (DHPMs) derivatives asymmetrically. Various techniques were used to confirm its structural properties. The Cu(ii)-salen complex was optimized to fit into the MWW support while maintaining its chirality through computer-assisted DFT calculations. This organocatalyst exhibited potent catalytic activity and could be reused multiple times without significant loss of activity.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Inorganic & Nuclear
Priyanka Devi, Kiran Singh, Bhupender Kumar, Jahnavi Kumari Singh
Summary: Many pyrazoles-based Schiff bases were reported to exhibit high activity against bacterial, parasitic strains, and cancer cells. A new pyrazole based 'NO' bidentate ligand was synthesized and metal complexes with Co+2, Ni+2, Cu+2, and Zn+2 were also prepared. The characterization of the compounds and their metal complexes was performed, and the metal complexes showed enhanced activity compared to the ligand. They exhibited significant anticancer and antibacterial activity, as well as antifungal activity.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Analytical
Jie-Yu Yue, Li-Ping Song, Ying-Hao Shi, Li Zhang, Zi-Xian Pan, Peng Yang, Yu Ma, Bo Tang
Summary: A chiral ionic covalent organic framework (COF) fluorescent sensor was developed for the recognition of the stereochemical configuration of phenylalaninol (PAL). The COF showed a turn-on fluorescent response for R-PAL over S-PAL, with an enantioselectivity factor of 16.96. The chiral selectivity was attributed to the stronger binding affinity between the COF and R-PAL compared to S-PAL. This study expands the applications of ionic COFs and provides new insights into the development of novel chiral fluorescent sensors.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Physical
Gulnur Keser Karaoglan
Summary: In this study, a new series of Schiff base metal complexes were synthesized and characterized. The thermal stability and photophysical properties of these complexes were investigated. The results showed that the metal ions affected the thermal strength and fluorescence quenching constant of the complexes, with the Cu(II) complex exhibiting the highest thermal strength. Due to their high fluorescence quenching constants, these complexes could be potential active ingredients in anticancer drug transport systems.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Physical
A. K. Khedr, R. R. Zaky, E. A. Gomaa, M. N. Abd El-Hady
Summary: A series of transition metal complexes were prepared using a novel ligand and various metal cations, and their structures, properties, and biological activities were extensively studied.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Biochemistry & Molecular Biology
Hanan B. Howsaui, Amal S. Basaleh, Magda H. Abdellattif, Walid M. Hassan, Mostafa A. Hussien
Summary: Three novel 2-aminopyrazine Schiff bases and their uranyl complexes were synthesized and characterized, with studies on DNA binding and anticancer activities showing promising results. Molecular docking analysis provided insights into interactions with cancer proteins.
Article
Multidisciplinary Sciences
Satoshi Yamanaka, Yuto Horiuchi, Saya Matsuoka, Kohki Kido, Kohei Nishino, Mayaka Maeno, Norio Shibata, Hidetaka Kosako, Tatsuya Sawasaki
Summary: This article introduces a method based on AirID to identify drug-induced neo-substrates through proximity-dependent biotinylation. The study identifies several new CRBN substrates and demonstrates that this method can serve as a general strategy for studying drug-induced protein-protein interactions in cells.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hiroto Uno, Koki Kawai, Taichi Araki, Motoo Shiro, Norio Shibata
Summary: Gem-difluoromethylene moieties are attractive in medicinal chemistry due to their ability to mimic other more ubiquitous functional groups. A novel asymmetric method for their construction was developed, allowing easy access to chiral 1,3-dioxanes that contain a tetrasubstituted difluoroalkyl stereogenic center. The gem-difluoro substitution pattern promotes the reaction, and various substrates were suitable for this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ibon Alkorta, Rosa M. Claramunt, Jose Elguero, Enrique Gutierrez-Puebla, M. Angeles Monge, Felipe Reviriego, Christian Roussel
Summary: The reaction between NH-indazoles and formaldehyde in aqueous hydrochloric acid was experimentally studied using solution and solid-state nuclear magnetic resonance and crystallography. The mechanism of N1-CH2OH derivative formation was determined. For the first time, 2-substituted derivatives were characterized using multinuclear NMR. Theoretical calculations supported the experimental observations. Additionally, the X-ray structures of four new (1H-indazol-1-yl)methanol derivatives were reported.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Daiki Homma, Shuhei Taketani, Takeshi Shirai, Elsa Caytan, Christian Roussel, Jose Elguero, Ibon Alkorta, Osamu Kitagawa
Summary: In this study, N-methyl-2-methoxymethylanilines bearing various 5-substituted-pyrimidin-2-yl groups were synthesized and their rotational behaviors were investigated. The results revealed that the rotational barriers around the N-Ar bonds increase proportionally to the electron-withdrawing ability of the substituent X at the S position.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kentaro Iwaki, Koki Maruno, Osamu Nagata, Norio Shibata
Summary: The trans-tetrafluoro-lambda 6-sulfanyl (SF4) unit is of medicinal interest due to its high electronegativity, lipophilicity, and unique hypervalent structure. Despite the difficulties in synthesis, the first synthesis of (ethynyl-trans-tetrafluoro-lambda 6-sulfanyl) pyridines and their use as versatile reagents for SF4-alkynylation to carbonyl compounds was reported. The addition reaction of t-ethynyl-SF4-pyridines to carbonyl groups in the presence of MeLi yielded pyridine-SF4-propargylic tertiary and secondary alcohols in high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kentaro Iwaki, Kazuhiro Tanagawa, Soichiro Mori, Koki Maruno, Yuji Sumii, Osamu Nagata, Norio Shibata
Summary: In this study, we reported a metal-free hydration reaction of pyridine-SF4-alkynes under acidic conditions, which synthesized pyridine-SF4-methyl ketones with yields ranging from 59% to 93%. We further demonstrated the synthetic applications of these compounds, including chlorination, NaBH4 reduction, Baeyer-Villiger oxidation, and the generation of enol triflates. These compounds show promise as useful building blocks in the synthesis of a wide range of SF4-containing drug candidates.
Article
Chemistry, Organic
Jun Zhou, Bingyao Jiang, Zhengyu Zhao, Norio Shibata
Summary: A potassium base-mediated defluoroetherification method for aryl and heteroaryl fluorides is reported, which efficiently and safely provides a wide variety of aryl ethers without the use of metal catalysts, specific ligands, and harsh conditions. This method can also be applied to the late-stage etherification of structurally complex fluorides and bioactive alcohols.
Article
Chemistry, Organic
Yuji Sumii, Hiroto Iwasaki, Yamato Fujihira, Elsayed M. Mahmoud, Hiroaki Adachi, Takumi Kagawa, Dominique Cahard, Norio Shibata
Summary: A protocol for the stereodivergent pentafluoroethylation of N-sulfinylimines has been developed using HFC-125 with KHMDS/triglyme. The presence or absence of triglyme enables the selective synthesis of both diastereomers of the pentafluoroethylated amines. This additive-controlled protocol offers a straightforward and cost-effective alternative to the previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P4-tBu.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Masahiro Sugiura, Kazuki Ishikawa, Kota Katayama, Yuji Sumii, Rei Abe-Yoshizumi, Satoshi P. Tsunoda, Yuji Furutani, Norio Shibata, Leonid S. Brown, Hideki Kandori
Summary: This study reports a novel photochemical reaction mediated by a microbial rhodopsin, leading to the selective transition from the all-trans to 7-cis form.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Norio Shibata, Dominique Cahard
Summary: From 2000, our two research groups independently and simultaneously designed and developed a novel family of electrophilic fluorinating reagents based on the use of Cinchona alkaloids. The chiral N-fluoro ammonium salts demonstrated the highest efficiency compared to prior art in enantioselective electrophilic fluorination for a wide range of substrates. In this account, we tell our respective stories, how the same idea germinated in our laboratories, the characterization of the chiral reagents, the use in stoichiometric quantity then the development of a catalytic version, the application to the synthesis of chiral fluorinated molecules of pharmaceutical interest, and finally the exploitation of our reagents by other teams and for other applications.
Review
Chemistry, Multidisciplinary
Yuji Sumii, Norio Shibata
Summary: The trifluoromethyl group is a crucial component in drugs and polymers, making the development of trifluoromethylation reactions a significant area of research in organic chemistry. Various methods, including nucleophilic and electrophilic approaches, transition-metal catalysis, photocatalysis, and electrolytic reactions have been developed over the years. Microflow versions of these reactions have shown great potential for industrial applications due to their scalability, safety, and time efficiency. This review discusses the current state of microflow trifluoromethylation, focusing on different trifluoromethylation reagents and techniques such as continuous flow, flow photochemical, microfluidic electrochemical reactions, and large-scale microflow reactions.
Letter
Chemistry, Organic
Elsayed M. Mahmoud, Soichiro Mori, Yuji Sumii, Norio Shibata
Summary: The synthesis of acyl fluorides from carboxylic acids is achieved using Selectfluor mediated by elemental sulfur. A wide range of acyl fluorides can be accessed while avoiding the formation of acid anhydrides. F-19 NMR spectra indicate that the reactive species in this deoxyfluorination reaction are the in situ generated S-8-fluoro-sulfonium cation A and neutral S-8-difluoride A'.
Article
Multidisciplinary Sciences
Jun Zhou, Zhengyu Zhao, Norio Shibata
Summary: Defluorinative cross-coupling between amines and organic fluorides is achieved via a silylboronate-mediated strategy. This method enables the room-temperature cross-coupling of C-F and N-H bonds, avoiding the high energy barriers associated with thermally induced S(N)2 or S(N)1 amination. The selective activation of the C-F bond of organic fluorides by silylboronate is a significant advantage of this transformation.
NATURE COMMUNICATIONS
(2023)
Editorial Material
Chemistry, Multidisciplinary
Norio Shibata, Dinesh Talwar
Summary: The unique properties and applications of fluorine-containing molecules have had significant impact across different scientific fields, from small to large molecules. This special issue provides a comprehensive overview of the state-of-the-art in fluorine chemistry.
Article
Chemistry, Multidisciplinary
Jun Zhou, Zhengyu Zhao, Bingyao Jiang, Katsuhiro Yamamoto, Yuji Sumii, Norio Shibata
Summary: In this study, an efficient silylboronate-mediated cross-coupling reaction of aryl fluorides with arylalkanes was developed under transition-metal-free, room-temperature conditions. The method showed good adaptability to aryl fluorides with a C(sp(2))-F bond and can be extended to other coupling partners with a C(sp(3))-H bond. It provides a practical and convenient approach to obtain di- and triarylalkanes with tertiary or quaternary carbon centers.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
