Article
Chemistry, Organic
Manon Genet, Abdelilah Takfaoui, Jerome Marrot, Christine Greck, Xavier Moreau
Summary: An enantioselective organocatalytic reaction of indole-derived-1-azadienes with aldehydes has been reported, leading to the formation of enantioenriched cyclic N,O-acetals. The corresponding products can be obtained with high levels of stereoselectivity, and fused tetracyclic scaffolds can also be obtained using a one-pot strategy.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Yueteng Zhang, Peng Ji, Xiang Meng, Feng Gao, Fanxun Zeng, Wei Wang
Summary: A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes, which involved the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.
Article
Chemistry, Organic
Christian B. J. Breuers, Constantin G. Daniliuc, Armido Studer
Summary: The stereoselective intramolecular dearomatizing spirocyclization of indoles via oxidative N-heterocyclic carbene (NHC) catalysis to afford indolenines bearing an all-carbon quaternary center at the 3-position is described. The reaction proceeds through the intramolecular nucleophilic addition of the indole to an in situ generated α,β-unsaturated acyl azolium.
Article
Chemistry, Organic
Timothy J. Paris, Chris Schwartz, Rachel Willand-Charnley
Summary: The successful synthesis and isolation of heteroaryl ketene acetals were achieved through intermolecular transfer of alkoxyl from electrophilic peroxides to lithiated benzofurans, indoles, and pyridines, showing enhanced reactivity towards electrophilic oxygen. The stability of the heteroaryl ketene acetals throughout purification techniques was superior, possibly due to increased aromaticity of the indole and pyridine structures. The reported products demonstrated resilience to workup and flash column chromatography procedures, overcoming typical issues associated with alkyl ketene acetal synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Suhas Balasaheb Mitkari, Alberto Medina-Ortiz, Jose Luis Olivares-Romero, Miguel A. Vazquez, Eduardo Pena-Cabrera, Clarisa Villegas Gomez, David Cruz Cruz
Summary: The study introduces an aminocatalytic privileged diversity-oriented synthesis (ApDOS) strategy for constructing diverse and complex thiopyrans-piperidone fused rings, as well as facilitating a super cascade reaction to assemble nine fused rings. Furthermore, by linking an indole moiety on the dithioamide, a Pictet-Spengler type reaction can be promoted, leading to the synthesis of more complex fused ring derivatives in a one-pot process. This investigation opens up new perspectives for the synthesis of a new class of complex and diverse thiopyrans, expanding the chemical space.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Romain Melot, Sandra Olivero, Veronique Michelet
Summary: A synthetic route for alkynylated saturated N-heterocycles was developed via a sequential combination of Shono oxidation and gold(I)-catalyzed alkynylation reaction. The electrochemical Shono oxidation enabled efficient access to various N,O-acetals through direct C-H bond functionalization of cyclic amines. The gold-catalyzed process allowed the introduction of aryl acetylene partners with different electron properties. Promising initial results on asymmetric version were obtained.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Qiongya Li, Chunlan He, Jiahui Su, Ying Shao, Shengbiao Tang, Jiangtao Sun
Summary: We report a rhodium-catalyzed reaction that efficiently synthesizes pyridazine derivatives from N-acyl pyridazinones and diazoacetates under mild reaction conditions. This reaction likely proceeds through a carbene insertion into a C=O bond and an unprecedented 1,4-N to-O acyl rearrangement reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Erika Mezo, Mihaly Herczeg, Fruzsina Demeter, Ilona Bereczki, Magdolna Csavas, Aniko Borbas
Summary: The reductive opening of cyclic acetals has been widely used in the introduction of protecting groups in synthetic organic chemistry. This study systematically investigated the efficacy of various reagent combinations in the regioselective cleavage of glucosidic 4,6-halobenzylidene acetals, leading to the successful introduction of versatile halobenzyl protecting groups. The study identified several reagent combinations that efficiently cleaved the acetal rings with high regioselectivity, demonstrating the potential for practical applications in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Diksha Rajput, Gowsia Jan, Muthu Karuppasamy, Nattamai Bhuvanesh, Subbiah Nagarajan, C. Uma Maheswari, J. Carlos Menendez, Vellaisamy Sridharan
Summary: An efficient cascade annulation reaction using secondary amine catalyst was developed for the synthesis of functionalized 2H-chromenes and 1,2-dihydroquinolines with a p-quinone methide scaffold. The microwave-assisted strategy achieved high yields and completion of reactions in just 15 min. The synthesized products were further transformed into valuable compounds via a palladium-catalyzed double C-H bond activation process and epoxidation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Guangcai Xu, Gerrit J. Poelarends
Summary: The application of biocatalysis in challenging synthesis has greatly benefited from the development of new enzymes. By incorporating catalysis modes from synthetic chemistry, novel biocatalysts have been created, and the design of iminium catalysis plays a fundamental role in this process. It has been shown that repurposing existing enzymes or constructing artificial enzymes can promote valuable abiological transformations, demonstrating the power of combining chemomimetic biocatalyst design and directed evolution in generating new-to-nature enzymes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Shi-Lu Zheng, Long Chen
Summary: 2H-chromenes, as an important type of oxygen heterocycles, are widely found in natural products, pharmaceutical agents, and biologically relevant molecules. The synthesis of such compounds mainly involves benzopyran ring formation and late-stage functionalization of the parent 2H-chromenes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Hongjun Jeon, Sang Won Choi, Soojun Park, Seokwoo Lee, Sanghee Kim
Summary: In this study, a facile method for generating O-acyloxocarbenium ions (AOIs) from ester and acetal groups was presented, resulting in a unique bridged bicyclic system. The proposed mechanism for the reaction was based on experimental and computational studies, revealing the formation pathway through an epoxonium-like transition state.
Article
Chemistry, Organic
Bruce A. L. Sacchelli, Bianca C. Rocha, Leandro H. Andrade
Summary: An ultrafast methodology utilizing microwave irradiation was employed for the first time to construct novel highly functionalized 2-quinolinones from N-(o-ethynylaryl)-acrylamides (1,7-enynes). The method involved six key consecutive reactions, including a diastereoselective step, to achieve good overall yield of 2-quinolinone-fused gamma-lactones (up to 46%; 10 s).
Article
Chemistry, Multidisciplinary
Erika Linde, David Bulfield, Gabriella Kervefors, Nibadita Purkait, Berit Olofsson
Summary: This study combines nucleophilic aromatic substitution and hypervalent iodine-mediated arylations to achieve a transition-metal-free difunctionalization of N and O-nucleophiles, providing di-and triarylamines and diaryl ethers in one single step. The unique reactivity discovered with specifically designed fluorinated diaryliodonium salts unveils novel reaction pathways in hypervalent iodine chemistry. The methodology tolerates a wide variety of functional and protecting groups, allowing for easy derivatization of the products.
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: Here, we report a metal-free cascade cyclization reaction that constructs structurally novel polyheterocycles by utilizing a hypervalent iodine(III) reagent. Under ambient conditions, alkyne-tethered N-alkoxybenzamides undergo a 6-exo-dig cyclization/dearomatization process to generate diverse N-O fused spiro polyheterocycles in good to high yields. This method features short reaction times, broad substrate scope, easy handling, and shows promising antifungal activity against crop and forest pathogenic fungi.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Chen Guang Yu, Vimala Bondada, Hina Iqbal, Kate L. Moore, John C. Gensel, Subbarao Bondada, James W. Geddes
Summary: BTK activation plays a crucial role in the neuroimmune response after traumatic spinal cord injury. Inhibiting BTK activity with Ibrutinib can attenuate the neuroimmune cascade and improve locomotor recovery.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Genetics & Heredity
Qianqian Li, Xiaofan Zhu, Chenguang Yu, Lin Shang, Ranran Li, Xia Wang, Yaping Yang, Jingjing Meng, Xiangdong Kong
Summary: This study describes a case of external ophthalmoplegia with rib and vertebral anomalies (EORVA) in an 8-year-old boy. A novel homozygous mutation in the myogenic factor 5 gene (MYF5) was identified using trio-based exome sequencing. Functional experiments showed that the mutant MYF5 led to decreased expression and production of a truncated protein.
FRONTIERS IN GENETICS
(2022)
Article
Cardiac & Cardiovascular Systems
Qianqian Li, Ziguan Zhang, Shanshan Chen, Zhengrong Huang, Mengru Wang, Mengchen Zhou, Chenguang Yu, Xiangyi Wang, Yilin Chen, Dan Jiang, Dunfeng Du, Yufeng Huang, Xin Tu, Zhishui Chen, Yuanyuan Zhao
Summary: The study demonstrated the role of miR-190a-5p in regulating IL-2 and SCN3B in the progression of CAs, suggesting miR-190a-5p as a potential protective factor in the pathogenesis of CAs.
FRONTIERS IN CARDIOVASCULAR MEDICINE
(2022)
Article
Multidisciplinary Sciences
Peng Ji, Cassondra C. Davies, Feng Gao, Jing Chen, Xiang Meng, Kendall N. Houk, Shuming Chen, Wei Wang
Summary: The synthesis of polycyclic structures bearing partially saturated (hetero)arenes is important. The authors develop a one-step method for selective dearomative functionalization of feedstock (hetero)arenes via organophotocatalysis. The method allows for rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yi Wan, Yumo Zhao, Jiajie Zhu, Qiyang Yuan, Wei Wang, Yongqiang Zhang
Summary: A metal-free catalytic approach for silyl transfer of silylboranes has been developed using a visible light-induced organophotocatalytic strategy. The protocol allows for the formation of various types of C-Si bonds by slightly adjusting the reaction conditions. This technology can also be applied to the construction of C-B, C-S, and C-Sn bonds, providing a versatile platform for bond activation and connection of main group elements. The green aspect of the reaction has been demonstrated by using Brij-30/water as a reaction solvent or sunlight as an alternative energy source.
Article
Pharmacology & Pharmacy
Jing Chen, Peng Ji, Giri Gnawali, Mengyang Chang, Feng Gao, Hang Xu, Wei Wang
Summary: The current targeting drug delivery primarily relies on cancer cell surface receptors; however, the binding affinity between protein receptors and homing ligands is often low and the expression level between cancer and normal cells is not significantly different. In contrast, a new approach has been developed by building an artificial receptor on the cancer cell surface through a chemical remodeling of cell surface glycans. This strategy involves the installation of a tetrazine-labeled chemical receptor on cancer cells as an overexpressed biomarker, allowing for the local activation and release of active drugs via a unique bioorthogonal reaction.
ACTA PHARMACEUTICA SINICA B
(2023)
Article
Chemistry, Multidisciplinary
Mengyang Chang, Feng Gao, Devin Pontigon, Giri Gnawali, Hang Xu, Wei Wang
Summary: A bioorthogonal on-demand prodrug strategy was developed to selectively activate and release PROTACs in cancer cells. The strategy utilizes a Tetrazine-modified RGD peptide as an activation component for targeted degradation of proteins of interest (POIs) in cancer cells. The results demonstrate selective activation of the PROTACs in an integrin alpha(v)beta(3)-dependent manner for protein degradation in cancer cells.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemical Research Methods
Feng Gao, Mengyang Chang, Xiang Meng, Hang Xu, Giri Gnawali, Yue Dong, Byrdie Lopez, Wei Wang
Summary: This article reports a method for selectively modifying secondary amines in peptides, proteins, and natural products. By fine-tuning the electronic effect of ynones, the reactivity of the Michael acceptor can be controlled for selective reaction with structurally different secondary amines in complex structures and biological environments.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Yueteng Zhang, Junjie Zhang, Menglong Li, Yan Qiao, Wei Wang, Lu Ma, Kangdong Liu
Summary: Natural products are valuable resources for drug discovery and development due to their diverse chemical structures and wide range of biological activities. However, identifying the biological targets of these compounds has been challenging. In recent studies, a simple and practical chemical tool called NCCB has been developed for target identification of natural products. This method has been successfully used to identify the direct targets of over 60 natural products.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zichao Lian, Fan Wu, Jiangzhi Zi, Guisheng Li, Wei Wang, Hexing Li
Summary: Efficient utilization of infrared light is achieved by the discovery of CuS@ZnS shell nanocrystals with strong localized surface plasmon resonance (LSPR) characteristics. These nanocrystals exhibit enhanced photocatalytic activity in hydrogen evolution reaction (HER) and possess high activity and stability under near-infrared light irradiation. The plasmon-induced defect-mediated carrier transfer (PIDCT) at the heterointerfaces of the nanocrystals provides a viable strategy for tuning LSPR-generated carrier kinetics and improving photocatalytic performance.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Correction
Chemistry, Organic
Yue Dong, Peng Ji, Yueteng Zhang, Changqing Wang, Xiang Meng, Wei Wang
Article
Chemistry, Multidisciplinary
Peng Ji, Xiang Meng, Jing Chen, Feng Gao, Hang Xu, Wei Wang
Summary: Photoredox mediated single electron transfer (SET) oxidation can reversely activate electron rich aromatics, enabling their dearomatization under mild conditions. This method offers high selectivity for the dearomatization and functionalization of electron rich heteroarenes.
Article
Chemistry, Multidisciplinary
Jing Chen, Huong T. X. Nguyen, Ming Yang, Fangxun Zeng, Hang Xu, Fu-Sen Liang, Wei Wang
Summary: Molecular glues have become a promising strategy for manipulating cellular functions and developing novel therapies for human diseases. Theranostics, with both diagnostic and therapeutic capabilities at disease sites, can achieve both functions simultaneously with high precision. In this study, we introduce a theranostic modular molecular glue platform that integrates signal sensing/reporting and chemically induced proximity strategies to selectively activate molecular glues at desired sites and monitor activation signals. This novel molecular glue strategy has the potential for research and biomedical applications.
Correction
Critical Care Medicine
Chen Guang Yu, Kate L. Moore
JOURNAL OF NEUROTRAUMA
(2022)