Article
Biochemistry & Molecular Biology
Grigorii S. Astakhov, Rinat R. Shigaev, Tatiana N. Borisova, Anastasia A. Ershova, Alexander A. Titov, Alexey V. Varlamov, Leonid G. Voskressensky, Maria D. Matveeva
Summary: A convenient protocol for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines with various electron-withdrawing substituents at C-2 atom is described. This approach is based on the two-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines with alpha,beta-unsaturated ketones, nitroalkenes and acrylonitrile. Depending on the selected substrates, the reaction was performed in TFE under reflux or under microwave irradiation. Only for the two examples, a transition metal catalyst was used.
MOLECULAR DIVERSITY
(2021)
Article
Chemistry, Multidisciplinary
Jianyi Shi, Zheng Zeng, Shengting Xu, Zechun Cai, Yuehua Luo, Yongbo Fan, Zhongzhi Zhu, Tingting Wen, Xiuwen Chen
Summary: In this study, a method for forming C(sp3)-C(sp2) bonds via copper catalyst-promoted cross coupling was developed. The reaction involved the sequential functionalization of the N1, C3, and C1 positions of 3-haloisoquinoline, resulting in the formation of new C-N, C=O, and C-C bonds. This method enables the efficient synthesis of 1,2-disubstituted isoquinolinones.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Kritika Laxmikeshav, Akash P. Sakla, Stephy Elza John, Nagula Shankaraiah
Summary: A facile and proficient dithiocarbamation of imidazo[1,2-a]pyridines and other imidazoheterocycles is established using a copper(i) catalyst and molecular oxygen under microwave conditions, resulting in moderate to excellent yields. The synthesized derivatives have drug-like properties and good ADME/T profile, with compounds 3be and 3bb showing more potency towards MCF-7 human breast cancer cells compared to the standard drug 5-fluorouracil.
Article
Chemistry, Organic
Ramesh Vediyappan, Natarajan Savitha Devi, Rameshbabu Ajaydev, Sivakumar Shanmugam
Summary: A facile method for the synthesis of novel compounds 7 and 8 has been developed, utilizing readily available starting materials and achieving high yields. Notably, the reaction is characterized by its short reaction time, simplicity in workup, and scalability.
TETRAHEDRON LETTERS
(2023)
Article
Biochemistry & Molecular Biology
Almira R. Miftyakhova, Tatiana N. Borisova, Alexander A. Titov, Matvey B. Sidakov, Roman A. Novikov, Ilya Efimov, Alexey V. Varlamov, Leonid G. Voskressensky
Summary: A novel synthetic method for obtaining highly functionalized compounds with potentially biologically active pharmacophore groups was developed through a three-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines, terminal alkynes, and CH-acids under microwave irradiation in dry acetonitrile.
CHEMISTRY & BIODIVERSITY
(2022)
Article
Chemistry, Organic
Charu Sharma, Avinash K. Srivastava, Deepak Sharma, Raj K. Joshi
Summary: This article presents a significantly upgraded Ullmann reaction for C-N cross couplings of aryl/alkyl chlorides. The method works in completely opposite conditions and is significantly influenced by various 3d transition metals, resulting in improved reaction time and catalytic activity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Multidisciplinary
Fu-Dong Lu, Jun Chen, Xuan Jiang, Jia-Rong Chen, Liang-Qiu Lu, Wen-Jing Xiao
Summary: Asymmetric transition metal catalysis with light intervention offers a practical alternative strategy for constructing complex organic molecules with excellent regio- and enantioselectivities. The recent advances in this field, including a concise analysis of substrate scope and mechanistic scenarios governing stereocontrol, provide a comprehensive understanding of the synthetic utility and potential of this methodology.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Applied
Liangying Wu, Yang Song, Zhanchong Li, Jiabao Guo, Xiaoquan Yao
Summary: A new method for generating fluoroalkylated arylamines under mild conditions with a wide substrate scope and excellent yields was developed using copper(II)-catalysed aerobic oxidative coupling. Preliminary studies suggest the reaction occurs via a radical mechanism, and the protocol offers an alternative green route for constructing fluorinated compounds by using atmospheric O2 as an oxidant.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Praveen Kumar Rathod, Kuntla Krishnaveni, Panaganti Leelavathi
Summary: A precise synthesis of benzimidazole-fused oxazepinoquinolines is presented in this study. The method involves three steps, including the conversion of 2-chloro-3-formylquinolines to 2-(2-bromoaryloxy) quinoline-benzimidazole conjugates, followed by a reaction with o-phenylenediamine and intramolecular cyclisation via CAN cross-coupling reaction under palladium catalysis. The protocol offers easily accessible starting materials, operational simplicity, broad substrate scope, and excellent yields.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Physical
Simon Garnier, Kevin Brugemann, Agnieszka Zak, Johnny Vercouillie, Marie Potier-Cartereau, Mathieu Marchivie, Sylvain Routier, Frederic Buron
Summary: The first access to N-1, N-4 disubstituted pyrrolo[2,3-d][1,2,3]triazoles is reported, and aryl groups were introduced at the C-5 and C-6 positions through regioselective electrophilic brominations followed by Suzuki-Miyaura cross coupling reactions.
Article
Chemistry, Organic
Almira R. Miftyakhova, Matvey B. Sidakov, Tatiana N. Borisova, Valentina V. Ilyushenkova, Artem N. Fakhrutdinov, Elena A. Sorokina, Alexey V. Varlamov, Leonid G. Voskressensky
Summary: The three-component domino reaction involving 1-aroyl-3,4-dihydroisoquinolines, terminal alkynes, and cyclic NH-acids is a new method for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines containing cyclic nitrogen-containing fragments at position 3.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Ge Wu, Xueying Zhou, Caihong Wang
Summary: A novel and efficient method for decarboxylative alkynylselenation of indoles using Se powder and propiolic acids as catalyst has been developed. This method avoids the use of prefabricated arylselenation reagent and over-seleniumation issues and enriches the chemistry of selenium powder. Furthermore, this reaction can be extended to pyrrole, and its practical utility has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Physical
Lei Chen, Xuemei Zhang, Mi Zhou, Lin Shen, Soren Kramer, Zhong Lian
Summary: A copper-catalyzed four-component enantioselective arylsulfonylcyanation of vinylarenes has been developed, providing easy access to chiral beta-sulfonyl nitriles with high yield and enantioselectivity. The use of a bench-stable SO2 surrogate (SOgen) is crucial for achieving excellent reactivities and enantioselectivities.
Article
Chemistry, Physical
Nasir S. Lawal, Halliru Ibrahim, Muhammad D. Bala
Summary: A set of facile room temperature catalytic systems were developed for the oxidation of cyclohexane C-H bonds using triazole-functionalised Schiff base copper complexes. The copper catalysts yielded high conversions to oxidised products with varying ratios of cyclohexanol and cyclohexanone. The kinetics study revealed an activation energy of 12.29 +/- 2 kJ/mol following a copper initiated radical mechanism.
Article
Chemistry, Organic
Ngoc-Khanh Nguyen, Duc Long Tran, Tran Quang Hung, Tra My Le, Nguyen Thi Son, Quang Thang Trinh, Tuan Thanh Dang, Peter Langer
Summary: BIM plays a crucial role in the structure of many bioactive compounds, and in this study, an air stable and convenient Cu(OAc)(2) catalyst was reported for the alkylation of indoles with alcohols to give bis(3-indolyl) methanes in very good yields.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Luca C. Greiner, Shinsuke Inuki, Norihito Arichi, Shinya Oishi, Rikito Suzuki, Tomohiro Iwai, Masaya Sawamura, A. Stephen K. Hashmi, Hiroaki Ohno
Summary: This study demonstrates the successful synthesis of benzannulated indole-fused medium-sized tetracycles through alpha-imino gold carbene chemistry, providing a new approach to explore bioactive compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Hiroki Komatsu, Takaya Ikeuchi, Hitomi Tsuno, Norihito Arichi, Kosuke Yasui, Shinya Oishi, Shinsuke Inuki, Aiko Fukazawa, Hiroaki Ohno
Summary: A novel method based on gold-catalyzed cascade cyclization of aminoallenynes for the direct construction of tricyclic nitrogen heterocycles is described. Efficient synthesis of 1,2-dihydrobenzo[cd]indole derivatives was achieved by promoting the expected biscyclization reaction of hydroxyisobutyryl-protected aminoallenynes with a catalytic amount of BrettPhosAuNTf(2) in the presence of iPrOH. The resulting tricyclic products were further converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) with highly conjugated pi-electron systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Takashi Kitamura, Rikito Suzuki, Shinsuke Inuki, Hiroaki Ohno, Kerry L. McPhail, Shinya Oishi
Summary: A coibamide A mimetic was designed with altered ester linkage and amino acid configurations in the macrocyclic structure, leading to the discovery of more potent derivatives. The structural-activity relationship study revealed a shared SAR with apratoxin A, suggesting a common binding site for the Tyr(Me) side chain at the luminal end of Sec61 alpha.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Luca C. C. Greiner, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: In this study, phenyl azides substituted by an (alkylphenyl)ethynyl group were found to facilitate benzylic sp(3)(C-H) functionalization under the presence of a JohnPhosAu catalyst, resulting in the synthesis of indole-fused tetra- and pentacycles through divergent N- or C-cyclization. The chemoselectivity of the reaction was found to be influenced by the counter-anion, the electron density of the alpha-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Atsuhito Tsuji, Takahiro Masuya, Norihito Arichi, Shinsuke Inuki, Masatoshi Murai, Hideto Miyoshi, Hiroaki Ohno
Summary: We identified a symmetric bis-sulfonamide compound, KPYC01112, as an inhibitor targeting NADH-quinone oxidoreductase. Structural modifications of KPYC01112 led to the discovery of more potent inhibitors 32 and 35. A photoaffinity labeling experiment with a newly synthesized photoreactive bis-sulfonamide revealed its binding to the subunits of complex I.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Biochemical Research Methods
Keisuke Aoki, Asako Manabe, Hiroyuki Kimura, Yohei Katoh, Shinsuke Inuki, Hiroaki Ohno, Motohiro Nonaka, Shinya Oishi
Summary: This study investigated the preparation protocols and biological properties of mirror-image proteins (d-VHHs), which have high-affinity binding to target proteins and reduced immunogenicity. The researchers established a synthetic process for model VHHs and their mirror-image proteins and found that the mirror-image proteins showed no binding to native proteins. Additionally, it was found that d-VHHs induced significantly lower levels of antibody generation compared to native VHHs.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Takuro Matsuoka, Akira Hattori, Shinya Oishi, Mitsugu Araki, Biao Ma, Toshiki Fujii, Norihito Arichi, Yasushi Okuno, Hideaki Kakeya, Sho Yamasaki, Hiroaki Ohno, Shinsuke Inuki
Summary: This study established an MR1 presentation reporter assay system using split-luciferase, which can efficiently explore MR1 ligands. Phenylpropanoid derivatives, including coniferyl aldehyde, were identified as MR1 ligands that can inhibit the MR1-MAIT cell axis. Further investigation revealed the key structural features required for MR1 recognition. These results have significant implications for identifying a wide range of MR1 ligands and developing novel MAIT cell modulators.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Yuki Yoshida, Haruka Takeuchi, Kohei Nakagawa, Toshiki Fujii, Norihito Arichi, Shinya Oishi, Hiroaki Ohno, Shinsuke Inuki
Summary: In this study, it was found that simple biphenyl substrates derived from amino acids can participate in a radical cascade reaction under visible light irradiation in the presence of [Ir{dF(CF3)ppy}(2)(dtbpy)]PF6, enabling the direct construction of bicyclo[2.2.2]octene structures. Isotopic labeling experiments suggested that intramolecular hydrogen atom transfer is involved in the cascade processes.
Article
Chemistry, Medicinal
Rikito Suzuki, Daphne R. Mattos, Takashi Kitamura, Rina Tsujioka, Kazuya Kobayashi, Shinsuke Inuki, Hiroaki Ohno, Jane E. Ishmael, Kerry L. McPhail, Shinya Oishi
Summary: In this study, novel lysine mimetics were designed and synthesized to enhance the cytotoxicity of coibamide A (CbA), a marine cyanobacterial cyclic depsipeptide that inhibits the mammalian protein secretory pathway. The introduction of ss- and epsilon-methyl groups led to a significant increase in cytotoxicity, while retaining the ability to inhibit secretion of a model Sec61 substrate. Tandem evaluation of secretory function inhibition in living cells and cytotoxicity proved to be an effective strategy for assessing the impact of structural modifications to the linker for ring closure.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Medicinal
Naoya Iwamoto, Yukino Sato, Asako Manabe, Shinsuke Inuki, Hiroaki Ohno, Motohiro Nonaka, Shinya Oishi
Summary: Mirror-image proteins are a promising scaffold for drug discovery due to their high proteolytic stability and low immunogenicity. In this study, a novel variant of a monobody was designed and synthesized to facilitate the synthetic process and improve protein stability. The synthetic mirror-image protein showed good binding affinity and low immunogenicity.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Medicinal
Takuro Matsuoka, Akira Hattori, Shinya Oishi, Mitsugu Araki, Biao Ma, Toshiki Fujii, Norihito Arichi, Yasushi Okuno, Hideaki Kakeya, Sho Yamasaki, Hiroaki Ohno, Shinsuke Inuki
Summary: In this study, a split-luciferase assay system was established to identify MR1 ligands, including phenylpropanoid derivatives. The structure-activity relationship analysis of coniferyl aldehyde analogs revealed the key features required for MR1 recognition. These findings will contribute to the identification of a wide range of endogenous and exogenous MR1 ligands and the development of novel MAIT cell modulators.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Satoshi Suzuki, Mio Kuroda, Keisuke Aoki, Kumi Kawaji, Yoshiki Hiramatsu, Mina Sasano, Akie Nishiyama, Kazutaka Murayama, Eiichi N. Kodama, Shinya Oishi, Hironori Hayashi
Summary: The rapid development of drugs against emerging and re-emerging viruses is crucial. Researchers have designed peptide inhibitors against SARS-CoV-2 using the screening system SPICA and structures predicted by AlphaFold2.
RSC CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Medicinal
Shinsuke Inuki, Hitomi Tabuchi, Chiaki Matsuzaki, Yasunori Yonejima, Keiko Hisa, Ikuo Kimura, Kenji Yamamoto, Hiroaki Ohno
Summary: Exopolysaccharides (EPSs) are widely present in natural products made by bacteria, fungi, and algae, and some of them have interesting biological properties such as anticancer and immunomodulatory activities. Our recent study found that EPSs derived from Leuconostoc mesenteroides ssp. mesenteroides strain NTM048 enhanced the production of mucosal immunoglobulin A (IgA) in mice. In this study, we described the synthesis and evaluation of tetrasaccharide fragments of NTM048 EPS to gain insights into the molecular mechanism responsible for the induction of IgA.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2022)
Review
Chemistry, Organic
Hiroaki Ohno, Shinsuke Inuki
Summary: This review discusses the nonbiomimetic total syntheses of indole alkaloids using alkyne chemistry, highlighting the importance of nonbiomimetic strategies in natural product synthesis and clarifying the differences between nonbiomimetic synthesis and biosynthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
