Article
Chemistry, Organic
Lijie Zhang, Ling Fang, Hao Huang, Chaofan Wang, Fang Gao, Zhiyong Wang
Summary: The study presents a novel and reliable method for synthesizing biologically interesting benzo[e][1,4]thiazepine derivatives in synthetically useful yields. Postsynthetic modification also leads to the formation of its sulfoxide and sulfone derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Liping Fu, Jing Wang, Xiaojuan Chen, Tao Shi, Zhanying Shao, Jinbai Chen, Chongmei Tian, Zhongdong Zhou, Huajian Zhu, Jiankang Zhang
Summary: An efficient synthesis of indolizines with a thioether group has been developed, forming a variety of target compounds with moderate to good yields. This transformation provides an alternative approach to previous protocols, with potential pharmaceutical and biomedical applications expected upon further development.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Thirupathi Reddy Penjarla, Adarash Kumar Shukla, Rituparna Hazra, Durba Roy, Maheshwar Kundarapu, Mudit Dixit, Anupam Bhattacharya
Summary: This article reports the synthesis of spiro compounds based on an indanedione-cyclopropane-pyrazolone framework. The reaction was carried out using the Michael-initiated ring closure strategy under Cu(OAc)(2) catalysis, assisted by an oxygen atmosphere and the base Et3N. The obtained compounds were mostly inseparable mixtures with modest to good yields using diverse substrates. Computational studies suggested that a route involving a four-membered Cu containing intermediate is feasible. The developed method has the potential to synthesize other analogous spiro systems.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Shuangrong Liu, Zhimin Ying, Qi Zhu, Xiuwen Zhong, Jie Cen, You Wu, Yongping Yu, Jiaan Shao, Wenteng Chen
Summary: This study reveals a step-economical nitrite-triggered cycloaddition reaction for the modular assembly of isoxazoles (or isoxazolines) from bromide and alkyne/alkene. The reaction offers high regio-selectivity, excellent efficiency, wide functionality tolerance, biocompatible conditions, and operational simplicity, making it suitable for the direct diversification of pharmaceuticals and bio-relevant motifs.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Hao-Jin Xu, Cui-Ting Li, Can-Ming Chen, Jie Chen, Xin-Qi Zhu, Bo Zhou, Long-Wu Ye
Summary: An efficient copper-catalyzed formal [4 + 1] annulation reaction of N-propargyl ynamides with diketones is described, enabling practical and atom-economic synthesis of valuable pyrrole-substituted dioxoles in generally moderate to excellent yields under mild reaction conditions. Thus, two new five-membered heterocycles can be constructed in one step through this vinyl cation chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Cheng Yuan, Jiatong Wang, Gangqiang Wang, Shaofa Sun, Jian Wang
Summary: This article describes an unprecedented example of synthesizing multi-substituted pyridazines via the [4+2] cycloaddition of azoalkenes generated in situ. The protocol has a wide range of substrate compatibility and allows for the rapid assembly of pyridazines. Importantly, this process provides an alternative method for in situ generation of azoalkenes.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chao Lin, Mao-Chang Wang, Peng Wie, Qi Xing, Chen-He Liu
Summary: A concise and efficient method for the synthesis of aziridines has been developed. The reaction proceeds through a [2+1] cycloaddition reaction of saccharin-derived cyclic ketimines with sulfur ylides. This methodology offers high atom-economy, broad substrate scope, and a simple procedure, resulting in excellent yields and diastereoselectivity (>20:1 dr). The aziridine products can be easily converted to benzothiazines through an unusual rearrangement reaction in the presence of base.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Radell Echemendia, Kleber T. de Oliveira, Antonio C. B. Burtoloso
Summary: A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides.
Article
Chemistry, Multidisciplinary
Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa
Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Pengwei Tan, Haoran Wang, Sunewang R. Wang
Summary: An unprecedented reductive [2 + 1] annulation of α-keto esters with alkynones mediated by P(NMe2)(3) has been described, leading to the formation of cyclopropenes with an unbiased alkene scaffold in good to excellent yields. This provides a promising complementarity to electrophilic metal-catalyzed cyclopropenation.
Article
Chemistry, Multidisciplinary
Ludovic Leleu, Thomas Martzel, Arona Fall, Morgane Sanselme, Vincent Levacher, Sylvain Oudeyer, Jean-Francois Briere
Summary: By utilizing metal- and catalyst-free electrochemical conditions in an undivided cell, a series of easily available redox-active N-(acyloxy)phthalimide esters were reacted with chiral C5-substituted azomethine imines, resulting in an efficient and highly stereoselective addition reaction to produce an array of polyaminated hydrazine derivatives.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yulong Wang, Shenyu Shen, Chonglong He, Youkang Zhou, Keyuan Zhang, Bin Rao, Tian Han, Yaqiong Su, Xin-Hua Duan, Le Liu
Summary: Here, we report a practical copper-mediated direct intramolecular cyclopropanation of distal olefinic acetate to synthesize cyclopropane-fused gamma-lactones and lactams. This cascade reaction proceeds through a hydrogen atom transfer-induced radical cyclization and copper-mediated cyclopropanation sequence. The protocol features high atom- and step-economy, excellent diastereoselectivity, broad tolerance of functional groups, and operational simplicity.
Article
Chemistry, Multidisciplinary
Jie Zhang, Xue Song, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A catalytic cyclopropanation reaction between benzyl bromides and activated alkenes has been developed using phosphonium ylide intermediates. The reaction produces densely functionalized cyclopropane derivatives with excellent diastereoselectivity, which can be further transformed into five-membered heterocycles. Moderate enantioselectivity can be achieved using a commercially available DuPhos catalyst.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Rong Zeng, Zheng Wang, Ruikun Peng, Peng Yan, Jie Yang, Qian Zhou, Jing Gu, Peng-Fei Zheng, Ying-Chun Chen, Qin Ouyang
Summary: Through density functional theory (DFT) calculations, the mechanism of the (4 + 1 + 1) annulations between alpha-bromo carbonyls and 1-azadienes was investigated, and the formation of a carbon anion intermediate and its attack on another alpha-bromo carbonyl substrate in a (4 + 1 + 1) manner were proposed as more reasonable processes. Based on this, a new controllable divergent (4 + 1 + 1 ') reaction was achieved by changing the feeding sequence of two different alpha-bromo substrates in the presence of tertiary amines and bases, resulting in the efficient construction of a series of fused benzofuro[3,2-b]pyridines or benzo[4,5]thieno[3,2-b]pyridines with more functional diversity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jianfeng Zheng, Lin Yang, Xin Dai, Lvli Chen, Luhao Tang, Yuqiao Zhou, Wei-Dong Z. Li
Summary: Magnesium-(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides were conducted. The method showed high tolerance towards different functional groups and had a wide range of substrates. A series of anti-pentacyclic spiroindolines with N,N'-fused heterocycle skeletons were obtained in good yields (up to 82%) with high selectivity (8.5:1 dr) under mild conditions. Interestingly, a sequential HOAc-mediated protonation led to diastereoenriched epimerization, resulting in the formation of exclusively syn-pentacyclic spiroindolines.
Article
Agriculture, Multidisciplinary
Hongbin Fang, Zhanfang Chen, Yang Liu, Tiancheng Zhang, Jing Chang, Zizheng Li, Lingxiao Zhang, Junkang Sui, Jing Ru, Yucheng Gu, Xuewen Hua
Summary: The development of new green fungicides is an effective way to solve the resistance of agricultural pathogens and plays an important role in promoting high-quality and sustainable development of modern agriculture.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Guantian Yang, Cong Zhou, Yutong Wang, Yuxin Li, Yucheng Gu, Zhong Li, Jiagao Cheng, Xiaoyong Xu
Summary: To develop novel chemotypes of anthranilic diamides, a series of anthranilic diamides with acrylamide linkers were synthesized. The compounds with a monofluoroalkene amide linker showed good larvicidal activity against lepidopteran pests. Compound A23 exhibited similar symptoms as chlorantraniliprole and had a better binding potency to P. xylostella RyR. This study explored the feasibility of using fluoroalkenes as insecticide fragments.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Plant Sciences
Xin He, Guoqing Peng, Jianying Luo, Jian-Ping Huang, Jing Yang, Yijun Yan, Yu-Cheng Gu, Li Wang, Sheng-Xiong Huang
Summary: Six new azoxy-aromatic compounds and two new nitrogen-bearing phenylvaleric/phenylheptanoic acid derivatives were isolated from Streptomyces sp. Py50 and their structures were elucidated. Compounds 1, 5, and 6 exhibited anti-fungal activity against Epidermophyton floccosum with MIC50 values ranging from 10.1 to 51.2 μM. A possible biosynthetic pathway for compounds 2 and 3 was proposed.
JOURNAL OF NATURAL PRODUCTS
(2023)
Review
Chemistry, Multidisciplinary
Rui Zhang, Chang-Yang Song, Zhe Sui, Ye Yuan, Yu-Cheng Gu, Cheng Chen
Summary: Carbon-heteroatom bond formation without transition metals is a powerful synthetic method for efficiently synthesizing valuable molecules. This review presents selected examples and discusses the construction of C-N (including amination and amidation) and C-O (including etherification and hydroxylation) bonds under transition-metal free conditions. The involved catalysts/promoters, substrate scope, potential applications, and reaction mechanisms are systematically discussed.
Article
Biochemistry & Molecular Biology
Jia-Dong Yu, Ming-Zhi Su, Yu-Cheng Gu, Dan-Dan Yu, Li-Gong Yao, Shou-Mao Shen, Yue-Wei Guo, Hong Wang
Summary: Two new cembranoids, sarcoboettgerols D and E, along with four known compounds, were isolated from Sarcophyton boettgeri coral collected from Weizhou Island in the South China Sea. Their structures and configurations were determined by spectroscopic analysis, quantum mechanical nuclear magnetic resonance methods, and comparison with reported data. A possible biogenetic relationship of the four cembranoids was proposed. Sarcomililatin B exhibited cytotoxic activity against H1299 cells (IC50=35.0 μM), while both Sarcomililatin B and Sarcomililatin A showed moderate antibacterial activity (MIC 17.4-34.8 μg/mL).
CHEMISTRY & BIODIVERSITY
(2023)
Article
Chemistry, Multidisciplinary
Jiao Liu, Song-Wei Li, Qing-Min Zhao, Zai-Yong Zhang, Li-Gong Yao, Yu-Cheng Gu, Le-Fu Lan, Yue-Wei Guo
Summary: Nanolobatone A, a compound with an unprecedented tricyclo[10.3.0.0(1,2)]pentadecane carbon skeleton, as well as four new polyoxygenated compounds and four rare endoperoxide-bridged casbane-type diterpenoids, were isolated from the Hainan soft coral Sinularia nanolobata. The structures of the new compounds were determined through extensive spectroscopic analysis, X-ray diffraction analysis, and time-dependent density functional theory/electronic circular dichroism calculations. A possible biosynthetic pathway for the new isolates was proposed. Bioassays showed that nanolobatone A exhibited weak antibacterial activity against the Gram-positive bacteria Streptococcus pyogenes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Medicinal
Zhiwei Li, Sheng Mei, Jiuyu Liu, Jingxuan Huang, Hao Yue, Tingjie Ge, Kang Wang, Xinzi He, Yu-Cheng Gu, Changliang Hu, Minghui Tong, Xuan Shi, Yanfang Zhao, Yajing Liu, Mingze Qin, Ping Gong, Yunlei Hou
Summary: This study optimized a series of novel dihydropteridone derivatives as potent inhibitors of PLK1. Compound 21g showed improved PLK1 inhibitory capability and significant anti-proliferative activities against tumor-derived cell lines. It also exhibited better pharmacokinetic characteristics compared to BI2536 in mice.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemical Research Methods
Hong-bing Sun, Rui Song, Bing Xia, Quan-wei Xiao, Yu-cheng Gu, Yan Zhou
Summary: This study aimed to enhance the molecular networking (MN)-based dereplication and visualization ability of potential anti-breast cancer xanthones from H. bellum to overcome the scarcity of xanthones mass spectral data in GNPS libraries. A combined strategy of seed mass spectra-based MN and various computational tools was introduced to facilitate the rapid recognition and targeted isolation of potential anti-breast cancer xanthones in H. bellum.
PHYTOCHEMICAL ANALYSIS
(2023)
Article
Multidisciplinary Sciences
Yun-Zhao Wang, Zhen-Hua Wang, Inbal L. L. Eshel, Bing Sun, Dong Liu, Yu-Cheng Gu, Anat Milo, Tian-Sheng Mei
Summary: The efficiency of the enantioselective nickel-catalyzed reductive cross-coupling of aryl aziridines with aryl iodides is improved through an electrochemical method. Beta-phenethylamines are produced in good to excellent enantioselectivity with broad functional group tolerance. The electroreduction-mediated turnover of the nickel catalyst is credited for the high efficiency of this method.
NATURE COMMUNICATIONS
(2023)
Article
Agriculture, Multidisciplinary
Zhanfang Chen, Hongbin Fang, Jing Chang, Tiancheng Zhang, Yanhong Cui, Lingxiao Zhang, Junkang Sui, Qingping Ma, Peisen Su, Juyuan Wang, Jing Ru, Yucheng Gu, Hengjia Zhang, Xuewen Hua
Summary: In this project, quinoline and quinolone-containing hydrazide compounds were synthesized and showed excellent and broad-spectrum fungicidal activity. Compound E8 was found to affect the plasma membrane of fungi, leading to changes in morphology and subcellular structure. Fusarium graminearum exhibited resistance to E8 through metabolic pathways related to l-glutamate, l-glutamine, and glutathione. Additionally, the study investigated the effects of compound E8 on wheat seedling growth and its toxicity to zebrafish. These findings provide valuable guidance for the discovery of novel fungicidal lead compounds and the exploration of new targets to combat drug resistance.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Hongbin Fang, Jing Chang, Tiancheng Zhang, Zhanfang Chen, Guiqing Wang, Yanhong Cui, Junkang Sui, Lingxiao Zhang, Chen Liu, Yucheng Gu, Xue-Wen Hua
Summary: Structure optimization based on natural products is an effective approach for developing new green fungicides. In this project, thirty-two novel hydrazide compounds derived from natural products were designed and synthesized. The fungicidal bioassays showed that these compounds exhibited excellent and selective activity against specific pathogens. Further investigations revealed the fungicidal mechanism and analyzed the structural factors influencing the bioactivity. These findings provide important guidance for the development and practical application of novel fungicides.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Guantian Yang, Yutong Wang, Cong Zhou, Yuxin Li, Yucheng Gu, Zhong Li, Zhiping Xu, Jiagao Cheng, Xiaoyong Xu
Summary: The research successfully synthesized 44 compounds containing monofluoroalkene and found that some of them exhibited excellent larvicidal activity against lepidopteran pests. Three-dimensional QSAR analysis and molecular docking were conducted to investigate the bioactivity mechanisms of these compounds. Additionally, typical symptoms caused by the compounds and the potential insecticidal mechanism were observed.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Plant Sciences
Hong-bing Sun, Hai-fei Zou, Bing Xia, Yu-cheng Gu, Wen-lin Wu, Yan Zhou
Summary: The phytochemical investigation of Tragopogon porrifolius L. using the Feature-Based Molecular Networking (FBMN) approach led to the targeted isolation of eleven ursane-type triterpenoids. Their structures were determined through extensive analysis of NMR and HRMS spectra data. These compounds were reported for the first time from this plant, with compounds 2, 3, and 6-9 representing unusual (18α,198)-ursane-type triterpenes. All the isolated compounds were evaluated for their antioxidant activities, and compound 3 showed high antioxidant activity in the DPPH assay, with an IC50 value of 24.19 ± 0.42% at 50 μM.
PHYTOCHEMISTRY LETTERS
(2023)
Article
Plant Sciences
Congcong Li, Leiqiang Gong, Yu Jiang, Xueyan Huo, Lijun Huang, Haoran Lei, Yucheng Gu, Dong Wang, Dale Guo, Yun Deng
Summary: This study demonstrates that the ethyl acetate fraction of S. officinalis (SOEA) has significant efficacy in the treatment of ulcerative colitis (UC) by inhibiting the PI3K-AKT/NF-B/STAT3 pathway to improve clinical symptoms, inflammatory response, mucosal barrier, and intercellular interactions.
Article
Marine & Freshwater Biology
Yi-Qian Han, Qun Zhang, Wei-Feng Xu, Yang Hai, Rong Chao, Cui-Fang Wang, Xue-Mei Hou, Mei-Yan Wei, Yu-Cheng Gu, Chang-Yun Wang, Chang-Lun Shao
Summary: Further investigation on Aspergillus versicolor, a fungus derived from a soft coral, using MS/MS-based molecular networking, led to the discovery of seven known cycloheptapeptides and one new cycloheptapeptide. The structure of the new compound was determined through spectroscopic analysis and its configuration was confirmed using Marfey's method. The synthesis of a derivative of one of the known cycloheptapeptides was successfully achieved and optimized. The anti-tubercular activities of the synthesized compounds were evaluated, revealing the importance of serine hydroxy groups and tryptophan residue in the activity.
MARINE LIFE SCIENCE & TECHNOLOGY
(2023)
