Article
Chemistry, Organic
Shengkun Guo, Xiaoyu Shen, Xiaoyun Chen, Huaguang Yu, Ying Han, Chaoguo Yan, Yaocheng Shi, Hong Hou, Shaoqun Zhu
Summary: This study presents a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The generation of selenium atom radicals through visible light irradiation of diselenides leads to radical addition with 1,3-dienes, resulting in the formation of allyl radical intermediates. Rapid Z/E isomerization enables thermodynamically favorable intermediate formation, facilitating copper-catalyzed stereoselective functionalization with different nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pei-shang Li, Qiao-qiao Teng, Ming Chen
Summary: Described here is a redox-neutral palladium-catalyzed photo-induced radical cascade domino Heck reaction between N-aryl acrylamide and vinyl arenes. A variety of bioactive oxindoles with an all-carbon quaternary center were synthesized. The reaction proceeds via an open-shell intermediate and occurs under mild reaction conditions, showing excellent functional group tolerance. Importantly, the synthesized products can be readily transformed into biologically active molecules, including (& PLUSMN;)-physostigmine and (& PLUSMN;)-physovenine.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Ninglin Li, Fuqiang Xiong, Ke Gao
Summary: An efficient cobalt-based catalytic system has been developed for the protodeboronation of various aryl and vinyl boronates, tolerating a wide range of functional groups. Additionally, the reaction has been extended to deuterodeboronation with D2O, offering a potential protocol for the synthesis of regiospecifically deuterated arenes and olefins.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Alla I. Vaskevych, Nataliia O. Savinchuk, Ruslan I. Vaskevych, Svitlana V. Shishkina, Mykhailo V. Vovk
Summary: 2-butenylquinazolin-4(3H)-ones can undergo intramolecular aza-Wacker cyclization to form methylene-substituted pyrrolo(pyrido)[2,1-b]quinazolinones when treated with the catalytic system Pd(OAc)(2)/PPh3/Cs2CO3/benzoquinone in dioxane or Pd(PPh3)(2)Cl-2/t-BuONa/Cs2CO3/benzoquinone in toluene. The latter catalytic system also reacts with pentenyl(hexenyl)quinazolin-4(3H)-ones, but leads to the formation of vinyl-substituted pyrrolo(pyrido)[2,1-b]quinazolinones via competition between aminopalladation of C-H multiple bonds and allylic C(sp(3))-H bond activation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Pablo Esteban, Fernando Herrera, Daniel San Martin, Amparo Luna, Pedro Almendros
Summary: Typical transition metal-catalyzed oxycyclization reactions can lead to the formation of different products via distinct mechanisms, such as the 5-endo cyclization to form dihydrofurans or the 3-exo-cyclization/sulfonylation cascade to generate trisubstituted epoxides. The current stoichiometry control of regioselectivity may offer unique opportunities for chemical transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Nityananda Ballav, Suman Dana, Mahiuddin Baidya
Summary: This study introduces a Pd(II)-catalyzed hydrocarbofunctionalization method for allyl amines connected to the picolinamide directing group. The approach is based on the concept of nucleopalladation and a wide range of indoles effectively participate to produce valuable tryptamine derivatives with high yields. Synthetic utilities are showcased through substrate diversification bearing bioactive core, Pictet-Spengler cyclization, and beta-carboline synthesis. A mechanistic study suggests an irreversible nucleopalladation step, while protodepalladation follows a reversible pathway.
Article
Chemistry, Organic
Nityananda Ballav, Suman Dana, Mahiuddin Baidya
Summary: The hydrocarbofunctionalization of allyl amines connected to the picolinamide directing group is developed under Pd(II) catalysis. The strategy is based on a nucleopalladation concept and can effectively produce indole derivatives. The synthetic utilities of this reaction, including the Pictet-Spengler cyclization and beta-carboline synthesis, were demonstrated. Mechanistic studies indicate that the reaction proceeds through an irreversible nucleopalladation pathway.
Editorial Material
Chemistry, Multidisciplinary
Reina Nonami, Yusei Morimoto, Kazuya Kanemoto, Yasunori Yamamoto, Tomohiko Shirai
Summary: This article introduces the research conducted by Tomohiko Shirai and his collaborators at the National Institute of Technology Kochi College, Chuo University, and Hokkaido University. The image illustrates the precedence of asymmetric decarbonylative C-C bond formation by the Ir/S-Me-BIPAM complex over aldehyde decarbonylation.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Reina Nonami, Yusei Morimoto, Kazuya Kanemoto, Yasunori Yamamoto, Tomohiko Shirai
Summary: We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. This asymmetric C-C bond formation is achieved through the decarbonylation of aldehydes catalyzed by chiral iridium complexes and the formation of an aryl-iridium intermediate. The reaction shows broad functional group compatibility and generates no waste apart from carbon monoxide.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Ying Wang, JianJun Yin, Yanfei Li, Xiuping Yuan, Tao Xiong, Qian Zhang
Summary: We report the successful copper-catalyzed asymmetric conjugate addition of beta-substituted alkenyl heteroarenes, one of the most challenging Michael acceptors, with alkenes. This method enables the synthesis of diverse chiral heteroarenes with good to excellent yields and excellent enantioselectivity. Moreover, the Michael addition products can be further transformed into valuable acyclic enantioenriched structures through chiral amine catalysis. Mechanistic studies suggest that the hydrocupration step may be the turnover-limiting step, and control experiments provide insights into the preferential alkene hydrocupration in the presence of beta-substituted alkenyl heteroarenes and the Ph-BPE-ligated CuH catalyst.
Article
Chemistry, Multidisciplinary
Akshi Tyagi, Sunita Mondal, Anmol, Vikas Tiwari, Tarak Karmakar, Subrata Kundu
Summary: The research demonstrates that the hydroamination of electron-deficient olefins can be efficiently carried out using the (CAAC)Cu-Cl catalyst at room temperature and under an open atmosphere, and the catalyst also shows excellent efficiency in the hydroaryloxylation and hydroalkoxylation of alkenes. Detailed computational studies reveal that the reaction proceeds via either a four-membered or a six-membered cyclic transition state containing the copper ion.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yuli He, Marino Borjesson, Huayue Song, Yuhang Xue, Daning Zeng, Ruben Martin, Shaolin Zhu
Summary: A new catalytic blueprint was reported in this study, merging the modularity of nickel catalysis for bond formation with the ability to enable a rather elusive 1,4-hydride shift at arene sp(2) C-H sites, thus allowing access to ipso/ortho-difunctionalized arenes from readily available aryl halides under mild conditions and exquisite selectivity profile.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Siqi Wang, Jian-Shu Wang, Zhengjie Le, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed dicarbonylation reaction has been developed for the synthesis of aryl esters from p-benzoquinones and aryl triflates using Cr(CO)(6) as the CO source. The reaction proceeds smoothly and efficiently, yielding a series of aryl esters in moderate to good yields (up to 90%).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaofeng Jie, Yingying Zhao, Qinglei Chong, Fanke Meng
Summary: A catalytic chemo- and enantioselective method for generating secondary benzylic copper complexes from Cu-B(pin) additions to 1,2-disubstituted aryl alkenes, followed by site-selective cyanation at either aryl group or benzylic position, is presented. The study identifies chiral Cu complexes that offer not only high enantioselectivity but also superior efficiency compared to achiral catalysts. This method also reveals an unprecedented mode of cyanation at the benzylic site through dearomative isomerization. The functionalization of the resulting alkylboron products provides valuable building blocks that are otherwise difficult to access.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xinrui Dong, Wenhua Jiang, Dexiang Hua, Xiaohui Wang, Liang Xu, Xiaoxing Wu
Summary: The addition of trifluoromethyl sulfonyl radicals to alkynes is a valuable method for constructing highly functionalized sulfonyl compounds. This process shows broad functional group compatibility and potential in drug discovery and chemical biology.
Article
Chemistry, Medicinal
Xiang Zhang, Ruisong Bai, Huan Xiong, Hongtao Xu, Wei Hou
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Multidisciplinary
Hongtao Xu, Yuang Gu, Shuning Zhang, Huan Xiong, Fei Ma, Fengping Lu, Qun Ji, Lili Liu, Peixiang Ma, Wei Hou, Guang Yang, Richard A. Lerner
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Review
Biochemistry & Molecular Biology
Yunfei Bian, Wei Hou, Xinrou Chen, Jinzhang Fang, Ning Xu, Benfang Helen Ruan
Summary: This perspective summarizes the progress in the discovery and development of GDH inhibitors for the treatment of Hyperinsulinism-hyperammonemia syndrome (HHS). It explores the pathogenesis of HHS and the potential binding sites, screening methods, and research models for GDH inhibitors. Future therapeutic perspectives and research directions are provided.
CURRENT MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hongtao Xu, Yan Wang, Hewei Dong, Yiyuan Zhang, Yuang Gu, Shuning Zhang, Yu Meng, Jie Li, Xiao Jie Shi, Qun Ji, Lili Liu, Peixiang Ma, Fei Ma, Guang Yang, Wei Hou
Summary: Click chemistry is a concept of using modular synthesis for rapid functional discovery. This report describes the development of a clickable C3-H selenylation of indole and highlights its potential in high-throughput medicinal chemistry and chemical biology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Pharmacology & Pharmacy
Wei Hou, Hewei Dong, Xiang Zhang, Yan Wang, Lin Su, Hongtao Xu
Summary: The pharmacological activities of organoselenium compounds are related to their ability to scavenge and induce reactive oxygen species (ROS), their oxidative properties, and their Se(0) release property. Incorporating selenium into small molecules, especially heterocycles and natural products, has great potential for altering the potency and selectivity of these molecules. Selenium will thus be crucial in drug discovery in the near future. This article summarizes the effects of different organoselenium species on cellular oxidative stress levels and correlates the structural properties of selenium-containing heterocycles and natural product derivatives with their biological activities and therapeutic applications, providing guidance for rational design of selenium-containing drugs.
DRUG DISCOVERY TODAY
(2022)
Article
Chemistry, Medicinal
Wei Hou, Hongtao Xu
Summary: This article summarizes and discusses the relationship between the pharmacological activities and chemical properties of selenium compounds and the strategic incorporation of selenium into organic molecules, as well as provides perspectives on future research directions.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Wei Hou, Hewei Dong, Ying Yao, Kangyin Pan, Guang Yang, Peixiang Ma, Hongtao Xu
Summary: This research proposes the development of clickable selenylation reactions for the synthesis of Se-containing compounds, aiming to boost the development of seleno-medicinal chemistry.
Article
Chemistry, Multidisciplinary
Hongtao Xu, Tingting Tan, Yiyuan Zhang, Yan Wang, Kangyin Pan, Ying Yao, Shuning Zhang, Yuang Gu, Wanting Chen, Jie Li, Hewei Dong, Yu Meng, Peixiang Ma, Wei Hou, Guang Yang
Summary: This study describes a substrate activation approach for the arylation of DNA-conjugated phenols. By using diaryliodonium salts as arylation reagents, the researchers achieved highly selective on-DNA arylation reactions with phenols and oximes, enabling late-stage modification of peptides and synthesis of DNA-tagged analogues of existing drug molecules.
Article
Chemistry, Medicinal
Jun Song, Chuqiao Pan, Jinxiu Li, Ruisong Bai, Ziying Zeng, Yunying Han, Zhao Chen, Wei Hou, Yong Li, Benfang Helen Ruan
Summary: The study found that alpha,beta-unsaturated carboxylic acids derivatives, such as GJ2 and GJ5, can effectively inhibit GLS1 activity with good stability and pharmacokinetics.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Plant Sciences
Qiwen Shi, Yu Meng, Shufen Deng, Ziyuan Zhang, Hewei Dong, Hongtao Xu, Wei Hou
Summary: In this study, a series of new C-14 amide substituted derivatives of dehydroabietic acid were designed, synthesized and evaluated for their anti-proliferative activity. Compound 20 showed the best anti-proliferative activity against four tumor cell lines (A549, HepG2, MCF-7 and HCT-116), with IC50 values ranging from 1.83 μM - 4.58 μM. Mechanistic studies suggested that compound 20 causes cell cycle arrest at the G2/M phase and induces apoptosis of HCT-116 tumor cells in a dose-dependent manner through the intrinsic mitochondrial signaling pathway. These results indicate that compound 20 is a promising starting point for further optimization.
PHYTOCHEMISTRY LETTERS
(2023)
Article
Chemistry, Medicinal
Wei Hou, Zhao Chen, Chuqiao Pan, Maowei Ni, Haoqiang Ruan, Jun Song, Shiying Lu, Aman Bhasin, Benfang Helen Ruan
Summary: By designing a series of diselenide compounds with a covalent linkage to the allosteric site of KGA, we successfully targeted the synthetic region and strengthened the interaction. Proteomic analysis confirmed the cross-linking between the diselenide compounds and the Lys320 residue at the KGA allosteric site. SAR analysis showed a correlation between growth inhibition and KGA inhibition, which was enhanced by TrxR inhibition. Importantly, the designed novel diselenides are glutaminase allosteric inhibitors that demonstrated in vivo efficacy and survival in the xenograft animal model.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Biochemical Research Methods
Kangyin Pan, Ying Yao, Yiyuan Zhang, Yuang Gu, Yan Wang, Peixiang Ma, Wei Hou, Guang Yang, Shuning Zhang, Hongtao Xu
Summary: The DNA-encoded chemical library (DEL) is a powerful hit selection technique in basic science or innovative drug discovery. To solve the issue of DNA barcode damage in conventional on-DNA copper-catalyzed azide-alkyne cycloaddition reaction, we have successfully developed the first DNA-compatible enolate-azide [3 + 2] cycloaddition reaction. This DEL chemistry has the advantages of metal-free reaction, high DNA fidelity, high conversions, broad substrate scope, and easy access to highly substituted triazoles.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Jinzhang Fang, Zhao Chen, Jun Song, Jinxiu Li, Yunying Han, Wei Hou, Wenxi Wang, Benfang H. Ruan
Summary: The study identified Soluplus as a promising molecular carrier for allosteric inhibitors, enhancing their solubility and in vivo efficacy to overcome the bottleneck of tumor glutaminolysis targeting.
RSC CHEMICAL BIOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Yiyuan Zhang, Wanting Chen, Tingting Tan, Yuang Gu, Shuning Zhang, Jie Li, Yan Wang, Wei Hou, Guang Yang, Peixiang Ma, Hongtao Xu
Summary: This study presents a general palladium-catalyzed procedure for the synthesis of phosphonates, phosphinates, and phosphine oxides from phenols mediated by sulfuryl fluoride. The method shows mild conditions, broad substrate scope, high functionality tolerance, and water insensitivity. The utility of this procedure is demonstrated through various applications including gram-scale synthesis, late-stage decoration of drugs and natural products, and on-DNA synthesis for a DNA-encoded library.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Huan Xiong, Yuang Gu, Shuning Zhang, Fengping Lu, Qun Ji, Lili Liu, Peixiang Ma, Guang Yang, Wei Hou, Hongtao Xu
CHEMICAL COMMUNICATIONS
(2020)
