Article
Chemistry, Organic
Guozhe Guo, Yong Yuan, Xiazhen Bao, Xuehui Cao, Tongzhi Sang, Jiayuan Wang, Congde Huo
Summary: The study presents a novel visible-light induced redox-neutral decarboxylative cross coupling reaction, which successfully synthesized a variety of symmetrical and unsymmetrical 3,3'-bisindolylmethane derivatives from indole-3-acetic acid NHPI esters and indoles. Additionally, the reaction can be easily adapted for the preparation of a wide range of diarylmethane derivatives.
Article
Chemistry, Multidisciplinary
Sanjeev Kumar, Ajay K. Singh
Summary: The study presents the development of a visible-light-driven modular micro-flow reactor for the synthesis of a fused N-heteroaryl scaffold and late-stage functionalization of pyrazolopyridines. The method offers a simple and efficient approach without the need for expensive oxidants or additional photo-catalysts.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xin Gong, Na Yu, Linghui Gu, Zheyu Li, Wenbo Ma, Fei Zhao
Summary: In this study, a rhodium-catalyzed C-H alkenylation/DG migration cascade for the synthesis of tetrasubstituted 1,3-enynes from N-phenoxyacetamides and 1,3-diynes has been achieved with the assistance of the acetamido directing group (DG). Alternatively, a rhodium-catalyzed [3 + 2] annulation for the synthesis of alkynylated benzofurans from the same set of substrates has also been achieved by simply changing the reaction conditions. This work highlights the tunable divergent synthesis of valuable compounds triggered by C-H activation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yogesh N. Aher, Amit B. Pawar
Summary: An external oxidant free Ru(II)-catalyzed C-H functionalization/annulation of primary benzylamines with sulfoxonium ylides has been developed for the synthesis of isoquinolines. The reaction utilizes free amine as a directing group, which is generally considered to be a poor directing group. This work presents the first example of Ru-catalyzed C-H functionalization of benzylamines under redox-neutral conditions. The detection of the amine-directed ruthenacyclic intermediate using high-resolution mass spectrometry corroborated the involvement of free amine as a directing group.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuanyuan Yue, Yan Yang, Chunying Sun, Junli Chao, Yaqing Ye, Xiaohui Guo, Jianming Liu
Summary: This study demonstrates the delivery of several polycyclic aromatic hydrocarbons through the copper-catalyzed aerobic oxidative C-H/C-H [4 + 2] annulation at room temperature, achieving dual aryl C-H functionalization. Mechanistic experiments show that the C-H bond cleavage on the indole and phenyl rings is not involved in the rate-limiting step.
Article
Chemistry, Multidisciplinary
Tamanna Rana, Arijit Ghosh, Yogesh N. N. Aher, Amit B. B. Pawar
Summary: We have developed a redox-neutral synthesis of 3,4-unsubstituted isoquinoline 1(2H)-ones using Cp*Co(III) catalyst and N-chloroamides as starting materials. The reaction is conducted at ambient temperature and utilizes vinyl acetate as a cost-effective and benign acetylene surrogate. The N-Cl bond of the N-chlorobenzamides acts as an internal oxidant, eliminating the need for an external oxidant. The reaction demonstrates broad substrate scope and can also be extended to N-chloroacrylamides, resulting in the formation of 2-pyridone derivatives through vinylic C-H activation.
Article
Chemistry, Organic
Sundaramoorthi Sarathkumar, Veerababurao Kavala, Ching-Fa Yao
Summary: A water-soluble and low-valent rhenium(I) catalyst has been described for the C2 alkenylation of N-pyridyl/N-pyrimidyl indole derivatives with ynamides under mild conditions using water as the solvent. The reaction results in high yields of C2-Z-selective alkenylation products.
Review
Chemistry, Physical
Thaipparambil Aneeja, Mohan Neetha, C. M. A. Afsina, Gopinathan Anilkumar
Summary: Manganese-catalyzed C-H activation has rapidly become a powerful tool in organic synthesis, with high selectivity, eco-friendliness, and a wide substrate scope. This strategy has been widely applied in medicinal chemistry, materials science, and natural product synthesis, showing significant advances from 2018-2020.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Sudeshna Mondal, Ratnadeep Bera, Deepan Chowdhury, Suman Dana, Mahiuddin Baidya
Summary: An enol-assisted regioselective arene C-H alkylation with maleimides is developed under redox-neutral ruthenium-(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C-H metalation step for this reaction.
Article
Chemistry, Organic
Guang Chen, Yue Wang, Jie Zhao, Xinying Zhang, Xuesen Fan
Summary: A one-pot cascade reaction of o-alkynylnitrobenzenes with maleimides was successfully achieved under Au(III)- Cu(II) relay/synergetic catalysis, leading to the formation of hydroxysuccinimide substituted indolin-3-ones. The reaction showed good atom economy, compatibility with a wide range of substrates bearing various functional groups, and significant antiproliferative activity in human cancer cell lines for the obtained products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yidi Li, Huiying Xu, Zhi Zhou, Lin Huang, Zhenhao Tang, Wei Yi, Xiaowei Wu
Summary: Efficient cascade reactions are highly desirable for their step-economy and convenience in synthesizing complex molecules. This article reports a rare four-step tandem reaction to prepare difficult-to-synthesize furo[3,4-c]pyridine-1,4-diones using acrylamides and 4-hydroxy-2-alkynoates. The reaction involves C-H activation, Lossen rearrangement, annulation, and lactonization, and offers good functional group tolerance, simple product isolation, and compatibility with room temperature and air. DFT calculations were conducted to understand the reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Shen Min Li, Wang Huai Wang, Hong Jiang Li, Fang Du, Ying Na Cui, Shu Jia Zhang
Summary: A series of isocoumarins were successfully synthesized through a one-pot cyclization reaction using mandelic acids and internal alkynes as raw materials, [RuCl2(p-cymene)](2) as the catalyst, and Cu(OAc)(2).H2O as the oxidant under reflux conditions in air. The established reaction conditions allowed for the exploration of various substrates, and it was found that aromatic aldehydes and aromatic acids also reacted smoothly in the system, providing moderate yields of the target products. Additionally, it was demonstrated that mandelic acids were converted into the corresponding benzoic acids as intermediates in the reaction.
Article
Chemistry, Organic
Teruhisa Tsuchimoto, Takahiro Johshita, Kazuhiro Sambai, Naoki Saegusa, Takumi Hayashi, Tomohiro Tani, Mana Osano
Summary: A new method for the formation of seven-membered carbon rings in heteroarylindoles reacting with different substrates was discovered in this study, and the two different annulation reactions could be controlled. The resulting tetracyclic products can be further extended through subsequent reactions to expand the p-conjugated region.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yi Luo, Lin Dong
Summary: An efficient synthetic method has been developed for the functionalization of bisindoles and indoles through catalyst-controlled C-H functionalization of pyrazolidinones and 1,3-diynes, providing a straightforward pathway with high selectivity for both chemoselectivity and regioselectivity challenges.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Smruti Ranjan Mohanty, Namrata Prusty, Tanmayee Nanda, Shyam Kumar Banjare, Ponneri C. Ravikumar
Summary: In this study, the ruthenium-catalyzed regioselective sp2(C-H) monoalkenylation of N-arylpyridones was demonstrated, where the pyridone served as a weakly coordinating directing group. Importantly, this methodology was effectively applied to the synthesis of various drug analogues, with high yields up to 93%. HRMS analysis also revealed the presence of a six-membered ruthenium complex.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xinming Li, Donglei Shi, Yihe Song, Yixiang Xu, Ying Gao, Wenjing Qiu, Xin Chen, Xiaokang Li, Yunyuan Huang, Yanjun Feng, Baoli Li, Yuan Guo, Jian Li
Summary: This study successfully developed two fluorescent turn-on probes (KXS-M1 and KXS-M2) for the highly selective and sensitive detection of monoamine oxidase A (MAO-A). Among them, KXS-M2 exhibited better fluorescence increment and sensitivity, and can be used for the diagnosis and treatment of heart failure.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Medicinal
Yunyuan Huang, Jiqun Wang, Jiaqi Liu, Donglei Shi, Xiaokang Li, Manjiong Wang, Taotao Lu, Bei Jiang, Conglong Xia, Houwen Lin, Yixiang Xu, Jian Li
Summary: This study developed a novel and rapid computer-guided combination drug-network-screening approach, which discovered a significant synergistic cardioprotective effect of the menthol-allethrin combination in vitro, providing a new synergistic mechanism and prospective agent for the treatment of heart failure.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2022)
Article
Pharmacology & Pharmacy
Zhifan Mao, Wenwen Liu, Yunyuan Huang, Tianyue Sun, Keting Bao, Jiali Feng, Alexey Moskalev, Zelan Hu, Jian Li
Summary: This study investigates the anti-aging effects of sulfonylurea drugs, specifically chlorpropamide, on various organisms. The findings suggest that chlorpropamide delays aging and reduces doxorubicin-induced senescence by interacting with mitochondrial ATP-sensitive K+ channels and mitochondrial complex II. The study also reveals that chlorpropamide increases mitochondrial reactive oxygen species levels, which are associated with longevity signals.
ACTA PHARMACEUTICA SINICA B
(2022)
Article
Chemistry, Medicinal
Xiaokang Li, Jinwen Li, Yunyuan Huang, Qi Gong, Yan Fu, Yixiang Xu, Junyang Huang, Haolan You, Dong Zhang, Dan Zhang, Fei Mao, Jin Zhu, Huan Wang, Haiyan Zhang, Jian Li
Summary: This study proposed a novel therapeutic strategy by merging the key pharmacophores of an antidepressant and an anti-AD drug to develop multi-target-directed ligands for the comorbidity of AD and depression. Compound 5 showed promising triple-target bioactivities and alleviated depressive symptoms and cognitive dysfunction in mouse models.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Conglong Xia, Manjiong Wang, Yunhui Guan, Yunfei Li, Jian Li
Summary: Aconitum episcopale is an important medicinal plant with detoxifying and antialcoholic properties. It is crucial to distinguish this plant species from others due to their morphological similarities and minimal chemical composition differences. This study obtained the complete chloroplast genome sequence of A. episcopale and compared it with other species in the same family and genus. The results provided a theoretical basis for molecular identification and phylogeny of A. episcopale.
SCIENTIFIC REPORTS
(2022)
Article
Genetics & Heredity
Conglong Xia, Manjiong Wang, Yunhui Guan, Jian Li
Summary: This study obtained the complete chloroplast genome sequence of ten medicinal plants of Aconitum species using sequencing technology and compared it with other species. The results showed similar structure and gene content among these genomes, and the chloroplast genome was found to be beneficial in determining the phylogenetic relationships and species identification of Aconitum species.
FRONTIERS IN GENETICS
(2022)
Article
Cell Biology
Jiqun Wang, Yunyuan Huang, Kaixuan Shi, Lingyuan Bao, Chaojiang Xiao, Tianyue Sun, Zhifan Mao, Jiali Feng, Zelan Hu, Zhenghan Guo, Jing Li, Bei Jiang, Wenwen Liu, Jian Li
Summary: The development of safe and effective therapeutic interventions to delay aging and reduce the risk of aging-related diseases is of great importance. Chinese herbal medicine, with its multiple components and targets, has shown potential in treating aging and complex diseases. This study found that Nicandra physalodes extract (HL0285) exhibited lifespan extension activity in Caenorhabditis elegans (C. elegans), improved healthspan, enhanced stress resistance, and delayed the progression of neurodegenerative diseases. HL0285 also ameliorated senescence in human lung fibroblasts and reversed liver function damage in aging mice induced by doxorubicin. The longevity effect of HL0285 in C. elegans was dependent on specific signaling pathways. Overall, HL0285 has demonstrated antiaging effects and should be further explored as a potential antiaging agent.
OXIDATIVE MEDICINE AND CELLULAR LONGEVITY
(2022)
Article
Pharmacology & Pharmacy
Yixiang Xu, Chao Zhang, Kai Jiang, Xinchun Yang, Feng Chen, Zhiyang Cheng, Jinlong Zhao, Jiaxing Cheng, Xiaokang Li, Xin Chen, Luoyifan Zhou, Hao Duan, Yunyuan Huang, Yaozu Xiang, Jian Li
Summary: To address the issue of separating ant-heart failure (HF) activity from glucose-lowering side-effects, the researchers conducted structural repurposing of the SGLT2 inhibitor EMPA. The optimized derivative JX01 showed weaker SGLT2-inhibitory activity and lower glucose-lowering side-effects, but better NHE1-inhibitory activity and HF mice cardioprotective effect. Furthermore, JX01 demonstrated good safety profiles and pharmacokinetic properties. This study provides a paradigm for discovering novel anti-HF drugs and indirectly highlights the importance of SGLT2-independent molecular mechanisms in the cardioprotective effects of SGLT2 inhibitors.
ACTA PHARMACEUTICA SINICA B
(2023)
Article
Chemistry, Medicinal
Jinlian Wei, Yongyun Li, Ruoxi Li, Xin Chen, Tiannuo Yang, Liang Liao, Yuqing Xie, Jin Zhu, Fei Mao, Renbing Jia, Xiaofang Xu, Jian Li
Summary: Propafenone, an FDA-approved antiarrhythmic medication, has been found to effectively inhibit the viability and homologous recombination pathway of conjunctival melanoma (CM) cells. The derivative D34, with promising structure-activity relationships, strongly suppressed CM cell proliferation, viability, and migration. Mechanistically, D34 increased gamma-H2AX nuclear foci and DNA damage by inhibiting the homologous recombination pathway, especially the MRE11-RAD50-NBS1 complex. Moreover, D34 dihydrochloride significantly suppressed tumor growth in a CM xenograft model without toxicity. This discovery suggests that propafenone derivatives targeting the MRE11-RAD50-NBS1 complex may provide a potential approach for CM therapy and enhance chemo- and radio-sensitivity.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Oncology
Xin Li, Xiaowei Wu, Shenyou Nie, Jidong Zhao, Yuan Yao, Fangrui Wu, Chandra Bhushan Mishra, Md Ashraf-Uz-Zaman, Bala Krishna Moku, Yongcheng Song
Summary: This study identified several small-molecule inhibitors that target MLL rearranged leukemia. These inhibitors showed significant suppression of characteristic gene expression, strong cellular anticancer activities, and low cytotoxicity. They serve as useful chemical probes for studying protein-protein interactions and as leads for developing drugs against MLL rearranged and other leukemias.
Article
Chemistry, Organic
Yidi Li, Huiying Xu, Zhi Zhou, Lin Huang, Zhenhao Tang, Wei Yi, Xiaowei Wu
Summary: Efficient cascade reactions are highly desirable for their step-economy and convenience in synthesizing complex molecules. This article reports a rare four-step tandem reaction to prepare difficult-to-synthesize furo[3,4-c]pyridine-1,4-diones using acrylamides and 4-hydroxy-2-alkynoates. The reaction involves C-H activation, Lossen rearrangement, annulation, and lactonization, and offers good functional group tolerance, simple product isolation, and compatibility with room temperature and air. DFT calculations were conducted to understand the reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yidi Li, Huiying Xu, Lin Huang, Zhi Zhou, Zhenhao Tang, Haifang Meng, Wei Zhang, Wei Yi, Xiaowei Wu
Summary: We developed an efficient and regioselective method for the synthesis of trisubstituted 2-pyridone derivatives using a rhodium-catalyzed cascade reaction. This protocol offers several advantages, including a reusable catalytic system, high regioselectivity, uncommon Lossen rearrangement, good functional group tolerance, mild reaction conditions, simple purification, and scalability. The reaction mechanism was investigated through deuterium labeling, KIE assays, control experiments, and DFT calculations. The role of the hydroxyl group on propargyl alcohols in determining the regioselectivity was demonstrated, and the origin of the observed preference for the Lossen rearrangement was probed through Mulliken atomic charge analysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Cell Biology
Donglei Shi, Wenwen Liu, Ying Gao, Xinming Li, Yunyuan Huang, Xiaokang Li, Tony D. James, Yuan Guo, Jian Li
Summary: This study presents a strategy to monitor and selectively eliminate senescent cells in mice during aging through controllable photodynamic therapy, which inhibited the age-related functional decline.
Article
Chemistry, Multidisciplinary
Yihe Song, Xinming Li, Donglei Shi, Tianyue Sun, Wenwen Liu, Xiaokang Li, Sicong Qiao, Xin Chen, Yuan Guo, Jian Li
Summary: In this study, a therapeutic prodrug was designed to specifically treat chronic renal failure by using a senescence-associated enzyme as a trigger. The prodrug showed promising results in improving kidney function in mice with the disease.
Letter
Biochemistry & Molecular Biology
Shuaishuai Ni, Qian Liu, Xin Chen, Lele Ding, Lili Cai, Fei Mao, Donglei Shi, Robert M. Hoffman, Jian Li, Lijun Jia
SIGNAL TRANSDUCTION AND TARGETED THERAPY
(2022)
