Article
Chemistry, Physical
Vincent Davenel, Chloe Puteaux, Christian Nisole, Fabien Fontaine-Vive, Jean-Marie Fourquez, Veronique Michelet
Summary: Efficient routes to access functionalized bicyclo[3.2.1]oct-2-ene and bicyclo[3.3.1]nonadiene via indium-mediated cycloisomerization of 1,6-enynes have been developed. The optimization of an atom-economical catalytic process using InCl3 led to high yields of up to 99% for the preparation of functionalized bicyclic adducts. The choice between 5-exo and 6-endo pathways in the cyclization reaction was influenced by the substitution of the alkynyl moiety, with electron-withdrawing groups favoring the exo isomer.
Article
Chemistry, Organic
Teng Jia, Shengyu Fan, Fengmian Li, Xiaohan Ye, Wenke Zhang, Zhiguang Song, Xiaodong Shi
Summary: The intermolecular hydro-amination of arylalkynes with aliphatic amine catalyzed by a combination of 1,2,3-triazole-coordinated gold(I) catalyst and Zn(OTf)(2) cocatalyst has been successfully achieved with good to excellent yields and regioselectivity. Compared to previous methods, this approach offers an alternative catalyst system for this fundamental chemical transformation with high efficiency and practical conditions.
Article
Chemistry, Organic
Andrea Serafino, Nicola Camedda, Matteo Lanzi, Nicola Della Ca, Gianpiero Cera, Giovanni Maestri
Summary: Trinuclear all-metal aromatic palladium clusters catalyze C-C forming reactions of polyunsaturated substrates, resulting in the synthesis of two new families of tricyclic compounds. The method exhibits peculiar regio- and diastereoselectivity, demonstrating the complementarity of trinuclear palladium complexes to their mononuclear peers. Preliminary studies on the mechanism of these polycyclization reactions revealed unique features of the homogeneous catalytic system.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wei-Cheng Zhao, Xin Wang, Juhua Feng, Ping Tian, Zhi-Tao He
Summary: A novel and straightforward palladium-catalyzed desymmetric [2+2+2] cycloaddition reaction has been established, leading to the diastereoselective preparation of widely existing fused tricyclic organic compounds in moderate to excellent yields. A one-step aromatization process provides facile access to benzene-containing tricycles from the above cycloaddition products.
Article
Chemistry, Physical
James H. Herbort, Remy F. Lalisse, Christopher M. Hadad, T. RajanBabu
Summary: Two intermolecular hydroalkenylation reactions of 1,6-enynes were demonstrated, leading to the formation of substituted 5-membered carbo- and heterocycles. The interactions of alkenes with a cobaltacyclopentene intermediate were found to be crucial, with unexpected beta-C-H activation observed in the case of acrylates. The reaction rate was dependent on the concentrations of cobalt, acrylate, and activator, indicating a complex mechanism involving multiple factors.
Review
Biochemistry & Molecular Biology
Sanjun Zhi, Hongjun Yao, Wei Zhang
Summary: This paper summarizes the recent development of radical reactions for the synthesis of difunctionalization cyclic compounds. Various methods including radical addition and cyclization of different compounds are discussed, and the use of radical initiators, transition metal catalysis, photoredox, and electrochemical conditions are included.
Article
Chemistry, Organic
Niaz Liaba, Junseong Lee, Chang Ho Oh
Summary: A practical and efficient method for synthesizing [6,6,6,5] tetracyclic fused ring steroid skeletons (8 a-i) has been developed using copper-catalyzed intramolecular [4+2] cycloaddition reaction of enyne-carbonyl substrates (7 a-i). The compound 8 a with OMe group at the aromatic ring was further employed to synthesize estradiol and estrone.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tian-Shu Zhang, Jing Li, Hua Sun, Shuai Liu, Jing Li, Yan Chen, Wen-Juan Hao, Bo Jiang
Summary: An efficient synthetic approach for the synthesis of cyclopentenones containing a C-C stereocenter using gold(I)-catalyzed Nazarov-type cyclization/1,6-addition of 1,3-enyne esters with p-quinone methides (p-QMs) is described. This tandem transformation showed satisfactory substrate scope and acceptable functional group compatibility, providing a novel protocol for the rapid assembly of cyclopentenones in good to excellent yields under mild reaction conditions.
Article
Chemistry, Organic
Erandi Liyanage Perera, Daesung Lee
Summary: In this study, a sequential inter- and intramolecular addition reaction on electron-deficient 1,3-diynes conjugated with a ketone, ester, or imide functionality is described. This process is effectively directed by a propargylic -OH or -NH functionality. Alcohols, amines, and thiols show excellent reactivity for the initial addition. The addition of amines occurs at ambient temperature, whereas other nucleophiles require high temperatures and a base additive.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Juyeon Kang, Ju Hui Lee, Junseong Lee, Chang Ho Oh
Summary: This article reports a synthetic method for [6,6,6]-tricyclic compounds using metal catalysts to cyclize ene-yne-aldehydes or enyne-carbonyl substrates. Compounds containing the CO2Me group are potential precursors of the natural product Lepenine.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ndidi U. N. Iwumene, Daniel F. Moseley, Robert D. C. Pullin, Michael C. Willis
Summary: Rhodium-catalyzed hydroacylation reactions can be used to synthesize linear α,β-unsaturated enone intermediates, which can be used to construct diverse substituted saturated O-, N-, and S-heterocycles in a one-pot process. The reaction conditions can be adjusted to selectively form O-heterocycles with high levels of diastereoselectivity.
Article
Chemistry, Organic
Anchal Saxena, Nayan Ghosh
Summary: A new multicomponent reaction method for the synthesis of complex organic scaffolds using copper catalysis and silica gel assistance in one pot has been developed. The reaction exhibits good diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Anchal Saxena, Nayan Ghosh
Summary: This article describes a Cu(II)-catalyzed and silica gel-assisted multicomponent reaction for the synthesis of hexahydrobenzofuran-3-carboxamide in one pot. The reaction proceeds via C-N coupling reaction and hydrative cyclization of ynamide intermediates. Importantly, the reaction exhibits good to excellent diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ting Zhou, Liangliang Yang, Ming Lang, Shiyong Peng
Summary: An efficient one-pot sequential annulation of 1,n-enynes with tosyl azide is reported, providing a series of novel N-alkyl 1,2,3-triazole-fused polycyclic scaffolds in moderate to excellent yields under mild reaction conditions.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Kousar Ghasemi, Mahdieh Darroudi, Marjan Rahimi, Hossein Rouh, Anju R. Gupta, Chun Cheng, Abbas Amini
Summary: A new green magnetic nanocatalyst was developed for the efficient one-pot synthesis of propargylamine and triazole derivatives, offering high yields and easy separation of the catalyst, demonstrating excellent environmental-friendly properties.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Dong Liang, Chen Yu, Xiaojun Qin, Xingye Yang, Xuhui Dong, Mingzhao Hu, Lupei Du, Minyong Li
Summary: In this study, three small-molecule fluorescent probes targeting c-Met were developed and their design strategies were explored. The probes exhibited fluorescence properties suitable for imaging and showed inhibitory activities against c-Met, particularly probe 16. Binding between the probes and c-Met was confirmed using fluorescence polarization assays and flow cytometry analysis. Cell imaging demonstrated that these probes could label c-Met on living cells. This research is of significance for the development of c-Met kinase inhibitors and tumor pathology research.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Xingye Yang, Xiaojun Qin, Huimin Ji, Lupei Du, Minyong Li
Summary: Bioluminescence imaging (BLI) is a widely used visual method for real-time detection of physiological and pathological processes. One of the most commonly used bioluminescent systems is the firefly luciferin system, which has been successfully applied in various fields such as analyzing physiological processes, monitoring the environment, diagnosing diseases, screening candidate drugs, and evaluating therapeutic effects.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xingye Yang, Mengzhen Li, Xiaojun Qin, Siyu Tan, Lupei Du, Chunhong Ma, Minyong Li
Summary: Researchers have discovered that the binding of phosphatidylserine (PS) to T-cell immunoglobulin and mucin domain containing protein-3 (Tim-3) can inhibit the activation of natural killer (NK) cells. They developed a photoswitchable ligand called photophosphatidylserine (phoPS) which mimics the effects of PS, and demonstrated its ability to modulate the function of NK cells and optically control acute hepatitis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Medicinal
Dong Liang, Chen Yu, Zhao Ma, Mingzhao Hu, Jiahui Wang, Xuhui Dong, Lupei Du, Minyong Li
Summary: In this study, the discovery of two series of parbendazole derivatives as tubulin inhibitors for the treatment of head and neck squamous cell carcinoma (HNSCC) was reported. Compound 9q exhibited the best pharmacological activities and pharmacokinetic properties, displaying reasonable inhibition activity on cell proliferation, induction of cell apoptosis, and suppression of cell migration and invasion.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Xiang Li, Minyong Li
Summary: Developing effective drug screening methods is crucial for antitumor drug research. Patient-derived xenograft (PDX) tumor animal models and zebrafish as a screening model organism enable accurate and rapid discovery of lead compounds in the preclinical stage, while elucidating tumor pathogenesis.
MEDICINAL RESEARCH REVIEWS
(2023)
Article
Chemistry, Medicinal
Zhenzhen Li, Siyue Ma, Ling Zhang, Shuxin Zhang, Zhao Ma, Lupei Du, Minyong Li
Summary: Targeted protein degradation strategies have been developed to explore new therapeutic avenues and tools for biological investigation. In this study, we introduce a novel approach called heat shock protein 90-mediated targeting chimeras (HEMTACs) to induce protein degradation by connecting a target protein to HSP90. We demonstrate the successful application of HEMTACs for cyclin-dependent kinase 4 and 6 (CDK4/6), highlighting their potential as a valuable addition to TPD strategies, particularly proteolysis-targeting chimera technology.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Teng Yuan, Kelton Radefeld, Chuan Shan, Carter Wegner, Erin Nichols, Xiaohan Ye, Qi Tang, Lukasz Wojtas, Xiaodong Shi
Summary: Here, we have reported an intermolecular asymmetric hydrative aldol reaction by using a vinyl-gold intermediate under ambient conditions. This reaction provides a base-free approach to β-hydroxy amides with high efficiency, yielding up to 95% and with over 50 examples. The use of vinyl gold intermediate as a reactive nucleophile and Fe(acac)(3) as a critical co-catalyst prevents undesired protodeauration, allowing the transformation to proceed under mild conditions with excellent functional group tolerance and stereoselectivity (>20:1 d.r. and up to 99% ee).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jingwen Wei, Yangyang Xing, Xiaohan Ye, Bao Nguyen, Lukasz Wojtas, Xin Hong, Xiaodong Shi
Summary: In this study, a new synthetic strategy for enantioselective 1,2-dihydropyridine synthesis was reported. Using the gold-catalyzed intermolecular condensation of amine and diyne-ene, the synthesis was achieved through a formal [3+2+1] fashion with up to 95% yield and up to 99% enantiomeric excess (e.e.).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Editorial Material
Chemistry, Multidisciplinary
Zhao Ma, Minyong Li
ACS CENTRAL SCIENCE
(2023)
Review
Pharmacology & Pharmacy
Zhenzhen Li, Siyue Ma, Shuxin Zhang, Zhao Ma, Lupei Du, Minyong Li
Summary: Targeted protein degradation strategies, such as PROTACs, are effective for intracellular protein degradation, but new technologies are emerging for the degradation of extracellular and membrane proteins. These technologies are still in their early stages of application, despite some progress in the field. In this review, we summarize and review the therapeutic potential of existing technologies for extracellular and membrane protein degradation.
DRUG DISCOVERY TODAY
(2023)
Article
Chemistry, Physical
Chenhuan Wang, Shuyao Zhang, Teng Yuan, Abiola Azee Jimoh, Maxwell Abreu, Chuan Shan, Lukasz Wojtas, Yangyang Xing, Xin Hong, Xiaodong Shi
Summary: Triazole-ruthenium carbene complexes (TA-Rus) are a new class of modified Grubbs catalysts that can achieve challenging olefin metathesis at higher temperatures without decomposition. Compared to previously reported N-tethered Ru-carbene complexes, TA-Ru complexes have higher reactivity and can be used for cross-metathesis, ring-closing metathesis, and dynamic covalent chemistry reactions.
Article
Chemistry, Analytical
Yuhao Chen, Tiantian Zhao, Zhuang Miao, Tianguang Huang, Meiyuan Chen, Yi Zhao, Ao Hai, Qingrong Qi, Ping Feng, Minyong Li, Bowen Ke
Summary: In this study, a selective bioluminescent probe (CBP 1) was designed, synthesized, and evaluated for the real-time detection of CES2. This probe offers a promising approach for understanding the physiological functions and underlying mechanisms of CES2.
Article
Chemistry, Multidisciplinary
Mengjia Liu, Ying He, Lukasz Wojtas, Xiaodong Shi
Summary: In this study, a recyclable isoG-star material was developed for selective extraction of Cs+, demonstrating good reusability. This new supramolecular macrocycle offers a practical platform for the environmentally friendly and highly effective treatment of radiocesium.
Article
Pharmacology & Pharmacy
Dong Liang, Chen Yu, Zhao Ma, Xingye Yang, Zhenzhen Li, Xuhui Dong, Xiaojun Qin, Lupei Du, Minyong Li
Summary: In this study, we identified parbendazole as a promising compound for the treatment of head and neck squamous cell carcinoma (HNSCC) through a batch query in the connectivity map. Parbendazole was found to inhibit the proliferation of HNSCC cell lines by targeting tubulin and disrupting microtubule polymerization. It demonstrated therapeutic effect and low toxicity in in vivo and in vitro anti-tumor evaluation.
ACTA PHARMACEUTICA SINICA B
(2022)
Article
Chemistry, Organic
Pei Zhao, Xiaokang Wu, Jie Li, Gaopan Dong, Yingai Sun, Zhao Ma, Minyong Li, Lupei Du
Summary: In this study, alkene-conjugated luciferins were designed and synthesized to develop new firefly bioluminescence substrates. The activities of these substrates were evaluated in vitro and in vivo. A novel luciferin analogue, AL3, showed a 100 nm red-shift in its maximum biological emission wavelength compared to d-luciferin.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
