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学者姓名：闫红
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Abstract ：
Background: Epidermal growth factor receptor (EGFR) is a validated and therapeutically amenable target, and inhibition of the EGFR signaling pathway has emerged as an attractive target for cancer therapy.Methods: The present work was designed to synthesize and evaluate the antiproliferative activity of a novel series of 3,9-dioxatetraasteranes as potential inhibitors of EGFR. All target compounds were evaluated for antiproliferative activity in vitro against A549 and HepG2 cell lines.Results: Among the target compounds, compound B13 displayed the most potent antiproliferative activity against A549 with IC50 = 4.31 mu M and HepG2 with IC50 = 6.92 mu M. In addition, a molecular docking study was performed to investigate the binding mode and binding capacity with EGFR (PDB code: 1M17).Conclusion: The results indicated that 3,9-dioxatetraasteranes may be promising potential EGFR inhibitors.
Keyword ：
EGFR inhibitors EGFR inhibitors A549 A549 HepG2 cell lines HepG2 cell lines antiproliferative activity antiproliferative activity 3,9-dioxatetraasteranes 3,9-dioxatetraasteranes molecular docking molecular docking
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| GB/T 7714 | Wang, Hongjun , Tian, Nana , Chu, Dongchen et al. Synthesis and Biological Evaluation of 3,9-Dioxatetraasteranes as Potential Inhibitors of Epidermal Growth Factor Receptor [J]. | LETTERS IN DRUG DESIGN & DISCOVERY , 2024 , 21 (3) : 552-558 . |
| MLA | Wang, Hongjun et al. "Synthesis and Biological Evaluation of 3,9-Dioxatetraasteranes as Potential Inhibitors of Epidermal Growth Factor Receptor" . | LETTERS IN DRUG DESIGN & DISCOVERY 21 . 3 (2024) : 552-558 . |
| APA | Wang, Hongjun , Tian, Nana , Chu, Dongchen , Yan, Hong . Synthesis and Biological Evaluation of 3,9-Dioxatetraasteranes as Potential Inhibitors of Epidermal Growth Factor Receptor . | LETTERS IN DRUG DESIGN & DISCOVERY , 2024 , 21 (3) , 552-558 . |
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Abstract ：
In this article, we have investigated the photochemical reactions of 4-aryl-4H-pyran and found that the structural symmetry had a significant influence on its photochemical behavior. When symmetric 4-aryl-4H-pyran was used, such as diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate, mainly underwent [2 + 2] photocycloaddition reaction. While asymmetric 4-aryl-4H-pyran, such as 2-amino-3-cyano-4-aryl-4H-pyrans, mainly underwent photocleavage reactions. To speculate the reaction mechanism, density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations were carried out at the B3LYP-D3/def2TZVP//B3LYP-D3/6-31G(d) level. The results showed that diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate underwent a two-step [2 + 2] photocycloaddition to give 3,9-dioxatetraasterane derivatives via an intermolecular and an intramolecular reaction. And the 2-amino-3-cyano-4-aryl-4H-pyran underwent a ring cleavage to produce the conjugated diene de-rivatives. To explain the different photochemical behaviors of 4-aryl-4H-pyrans, electron spin density, frontier molecular orbitals (FMOs) analysis, electron-hole analysis and root-mean-square-deviation (RMSD) analysis were performed. (c) 2022 Elsevier Ltd. All rights reserved.
Keyword ：
Photocleavage Photocleavage Photochemical ring contraction Photochemical ring contraction Photocycloaddition Photocycloaddition Theoretical calculation Theoretical calculation 4-Aryl-4H-pyran 4-Aryl-4H-pyran
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| GB/T 7714 | Wang, Shijie , Song, Xiuqing , Sun, Runzhi et al. Insight for the photochemical reaction of 4-aryl-4H-pyran: Experimental and theoretical studies [J]. | TETRAHEDRON , 2023 , 131 . |
| MLA | Wang, Shijie et al. "Insight for the photochemical reaction of 4-aryl-4H-pyran: Experimental and theoretical studies" . | TETRAHEDRON 131 (2023) . |
| APA | Wang, Shijie , Song, Xiuqing , Sun, Runzhi , Yan, Hong , Wang, Yeming . Insight for the photochemical reaction of 4-aryl-4H-pyran: Experimental and theoretical studies . | TETRAHEDRON , 2023 , 131 . |
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Abstract ：
In this study, the visible-light-driven [2 + 2] photocycloaddition of 1,4-dihydropyrazines in solution was reported. The N,N'-diacyl-1,4-dihydropyrazines with different substituents showed completely different reactivity under the irradiation of a 430 nm blue light-emitting diode (LED) lamp. N,N'-Diacetyl-1,4-dihydropyrazine and N,N'-dipropionyl-1,4-dihydropyrazine were the only compounds capable of undergoing a [2 + 2] photocycloaddition reaction, yielding syn-dimers and cage-dimers (known as 3,6,9,12-tetraazatetraasteranes) with overall yields of 76 and 83%, correspondingly. The substituent-reactivity effect on [2 + 2] photocycloaddition of N,N'-diacyl-1,4-dihydropyrazines was investigated by density functional theory calculations. The results show that the substituents have little influence on Gibbs free energy for the [2 + 2] photocycloaddition and mainly affect the excited energy, reaction sites, and the triplet excited-state structures of 1,4-dihydropyrazines, which are closely related to whether the reaction occurs. The results offer insights into the photochemical reactivity of 1,4-dihydropyrazines and an approach for constructing dimers of N,N'-diacyl-1,4-dihydropyrazines through a solution-based visible-light-driven [2 + 2] photocycloaddition, especially for the construction of 3,6,9,12-tetraazatetraasteranes. Compared with the solid-state [2 + 2] photocycloaddition of 1,4-dihydropyrazine, this photocycloaddition will be an efficient and environmentally friendly method for synthesizing tetraazatetraasteranes with the advantages of milder reaction conditions, simple operation, adjustable reaction amounts by omitting the cocrystal growth step, etc.
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| GB/T 7714 | Zhang, Xiaokun , Wei, Chaochun , Chu, Dongchen et al. Visible-Light-Driven [2+2] Photocycloaddition for Constructing Dimers of N,N'-Diacyl-1,4-dihydropyrazines: Experimental and Theoretical Investigation [J]. | JOURNAL OF ORGANIC CHEMISTRY , 2023 , 88 (19) : 13946-13955 . |
| MLA | Zhang, Xiaokun et al. "Visible-Light-Driven [2+2] Photocycloaddition for Constructing Dimers of N,N'-Diacyl-1,4-dihydropyrazines: Experimental and Theoretical Investigation" . | JOURNAL OF ORGANIC CHEMISTRY 88 . 19 (2023) : 13946-13955 . |
| APA | Zhang, Xiaokun , Wei, Chaochun , Chu, Dongchen , Yan, Hong , Song, Xiuqing . Visible-Light-Driven [2+2] Photocycloaddition for Constructing Dimers of N,N'-Diacyl-1,4-dihydropyrazines: Experimental and Theoretical Investigation . | JOURNAL OF ORGANIC CHEMISTRY , 2023 , 88 (19) , 13946-13955 . |
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Abstract ：
3,6-diazatetraasterane and 3,9-diazatetraasterane are diazatetraasterane derivatives and cage-dimers of 1,4-dihydropyridine in head-to-head or head-to-tail manner by the regioselective [2 + 2] photocycloaddition. They were synthesized and their structures were verified by NMR spectra, high-resolution mass spectrometry, and Single-crystal X-ray diffraction. The results showed that the molecular structure of 3,6-diazatetraasterane with a C 1 symmetric property and the 3,9-diazatetraasterane with a C 2 symmetric property. The molecular packing arrangement of 3,6-diazatetraasterane was in the zigzag-shape, and the 3,9-diazatetraasterane was in layer-like architecture. The non-covalent interaction (NCI) and Hirshfeld surface analysis were conducted to characterize and visualize the intramolecular and intermolecular interactions. The molecular electrostatic potential (MEP) was calculated to predict electrophilic and nucleophilic regions. The results will provide a theoretical basis for further studies on chemical properties and pharmacological application of the azatetraasterane derivatives. (c) 2022 Elsevier B.V. All rights reserved.
Keyword ：
Diazatetraasterane Diazatetraasterane Hirshfeld surface analysis Hirshfeld surface analysis X-ray crystal structure X-ray crystal structure Molecular electrostatic potential Molecular electrostatic potential Non -covalent interaction analysis Non -covalent interaction analysis NMR analysis NMR analysis
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| GB/T 7714 | Wang, Shijie , Wang, Yeming , Ge, Changwei et al. Insight for the synthesis and crystal structure of diazatetraasterane derivatives: Experimental and theoretical studies [J]. | JOURNAL OF MOLECULAR STRUCTURE , 2023 , 1273 . |
| MLA | Wang, Shijie et al. "Insight for the synthesis and crystal structure of diazatetraasterane derivatives: Experimental and theoretical studies" . | JOURNAL OF MOLECULAR STRUCTURE 1273 (2023) . |
| APA | Wang, Shijie , Wang, Yeming , Ge, Changwei , Sun, Runzhi , Wang, Huiqin , Yan, Hong . Insight for the synthesis and crystal structure of diazatetraasterane derivatives: Experimental and theoretical studies . | JOURNAL OF MOLECULAR STRUCTURE , 2023 , 1273 . |
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Abstract ：
The photocycloaddition of 1,4-dihydropyridines (1,4-DHPs)is amain approach to synthesize structurally complex compounds, whichare important intermediates for the preparation of cage compounds,such as 3,9-diazatetraasterane, 3,6-diazatetraasterane, 3,9-diazatetracyclododecane,and 6,12-diazaterakishomocubanes. The acquisition of different cagecompounds depended on the chemoselectivity, which is mainly causedby the reaction conditions and structural characteristics of 1,4-DHPs.This study aimed to investigate the effect of the structural characteristicson chemoselectivity in [2 + 2]/[3 + 2] photocycloaddition of 1,4-DHPs.The photocycloadditions were conducted on the 1,4-diaryl-1,4-dihydropyridine-3-carboxylicester with steric hindrance groups at the C3 position or chiralityat the C4 position irradiated by a 430 nm blue LED lamp. When the1,4-DHPs contained high steric hindrance groups at the C3 position,[2 + 2] photocycloaddition was the main reaction, resulting in 3,9-diazatetraasteraneswith a yield of 57%. Conversely, when the 1,4-DHPs were resolved toa chiral isomer, the main reaction was [3 + 2] photocycloaddition,producing 6,12-diazaterakishomocubanes with a yield of 87%. To investigatethe chemoselectivity and understand the photocycloaddition of 1,4-DHPs,density functional theory (DFT) and time-dependent DFT (TDDFT) calculationswere performed at the B3LYP-D3/def-SVP//M06-2X-D3/def2-TZVP level.The steric hindrance and excitation energy modulated by substituentsat the C3 position and chiral carbon at the C4 position were crucialfor the chemoselectivity in [2 + 2]/[3 + 2] photocycloaddition of1,4-DHPs.
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| GB/T 7714 | Zhang, Xiaokun , Song, Xiuqing , Shi, Jiwen et al. Chemoselective [2+2]/[3+2] Photocycloaddition of 1,4-Dihydropyridines: Experimental and Theoretical Investigation [J]. | JOURNAL OF ORGANIC CHEMISTRY , 2023 , 88 (13) : 9066-9076 . |
| MLA | Zhang, Xiaokun et al. "Chemoselective [2+2]/[3+2] Photocycloaddition of 1,4-Dihydropyridines: Experimental and Theoretical Investigation" . | JOURNAL OF ORGANIC CHEMISTRY 88 . 13 (2023) : 9066-9076 . |
| APA | Zhang, Xiaokun , Song, Xiuqing , Shi, Jiwen , Yan, Hong , Tian, Nana . Chemoselective [2+2]/[3+2] Photocycloaddition of 1,4-Dihydropyridines: Experimental and Theoretical Investigation . | JOURNAL OF ORGANIC CHEMISTRY , 2023 , 88 (13) , 9066-9076 . |
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Abstract ：
Dengue virus (DENV) is a major mosquito-borne human pathogen in tropical countries; however, there are currently no targeted antiviral treatments for DENV infection. Compounds 27 and 29 have been reported to be allosteric inhibitors of DENV RdRp with potent inhibitory effects. In this study, the structures of compounds 27 and 29 were optimized using computer-aided drug design (CADD) approaches. Nine novel compounds were synthesized based on rational considerations, including molecular docking scores, free energy of binding to receptor proteins, predicted Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) parameters, structural diversity, and feasibility of synthesis. Subsequently, the anti-DENV activity was assessed. In the cytopathic effect (CPE) assay conducted on BHK-21 cells using the DENV2 NGC strain, both SW-b and SW-d demonstrated comparable or superior activity against DENV2, with IC50 values of 3.58 +/- 0.29 mu M and 23.94 +/- 1.00 mu M, respectively, compared to that of compound 27 (IC50 = 19.67 +/- 1.12 mu M). Importantly, both SW-b and SW-d exhibited low cytotoxicity, with CC50 values of 24.65 mu mol and 133.70 mu mol, respectively, resulting in selectivity indices of 6.89 and 5.58, respectively. Furthermore, when compared to the positive control compound 3 '-dATP (IC50 = 30.09 +/- 8.26 mu M), SW-b and SW-d displayed superior inhibitory activity in an enzyme inhibitory assay, with IC50 values of 11.54 +/- 1.30 mu M and 13.54 +/- 0.32 mu M, respectively. Molecular dynamics (MD) simulations elucidated the mode of action of SW-b and SW-d, highlighting their ability to enhance pi-pi packing interactions between benzene rings and residue W795 in the S1 fragment, compared to compounds 27 and 29. Although the transacylsulphonamide fragment reduced the interaction between T794 and NH, it augmented the interaction between R729 and T794. In summary, our study underscores the potential of SW-b and SW-d as allosteric inhibitors targeting the DENV NS5 RdRp domain. However, further in vivo studies are warranted to assess their pharmacology and toxicity profiles.
Keyword ：
dengue virus dengue virus NS5-RdRp inhibitors NS5-RdRp inhibitors molecular docking molecular docking antiviral compounds antiviral compounds
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| GB/T 7714 | Zong, Keli , Li, Wei , Xu, Yijie et al. Design, Synthesis, Evaluation and Molecular Dynamics Simulation of Dengue Virus NS5-RdRp Inhibitors [J]. | PHARMACEUTICALS , 2023 , 16 (11) . |
| MLA | Zong, Keli et al. "Design, Synthesis, Evaluation and Molecular Dynamics Simulation of Dengue Virus NS5-RdRp Inhibitors" . | PHARMACEUTICALS 16 . 11 (2023) . |
| APA | Zong, Keli , Li, Wei , Xu, Yijie , Zhao, Xu , Cao, Ruiyuan , Yan, Hong et al. Design, Synthesis, Evaluation and Molecular Dynamics Simulation of Dengue Virus NS5-RdRp Inhibitors . | PHARMACEUTICALS , 2023 , 16 (11) . |
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Abstract ：
Polyoxometalates (POMs), as a class of multinuclear metal oxygen clusters, have promising biological activities. And their amino acid derivatives will lead to better pharmacological activity by the diversity in structures and properties. With reference to the anti-HIV-1 activities of PM-19 (K7PTi2W10O40) and its pyridinium derivatives, a series of novel Keggin-type POMs with amino acid as organic cations (A7PTi2W10O40) were synthesized by hydrothermal synthetic method. The final products were characterized by 1H NMR, Elemental analyzes and single crystal X-ray diffraction. All the synthesized compounds were obtained in the yields of 44.3-61.7% and evaluated the cytotoxicity and anti-HIV-1 activity in vitro. Compared with the reference compound PM-19, the target compounds had a lower toxicity to TZM-bl cells and a higher inhibitory activity against HIV-1. Among them, compound A3 showed higher anti-HIV-1 activity with IC50 of 0.11 nM than that of PM-19 with 4.68 nM. This study demonstrated that combination of Keggin-type POMs and amino acids can be a new strategy to enhance the anti-HIV-1 biological activity of POMs. All results will be expected to helpful for developing more potent and effective HIV-1 inhibitors.
Keyword ：
Anti-HIV-1 Anti-HIV-1 Polyoxometalates Polyoxometalates Synthesis Synthesis Biological activity Biological activity Amino acids Amino acids
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| GB/T 7714 | Tian, Nana , Chu, Dongchen , Wang, Hongjun et al. Synthesis and anti-HIV-1 activity evaluation of Keggin-type polyoxometalates with amino acid as organic cations [J]. | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 2023 , 91 . |
| MLA | Tian, Nana et al. "Synthesis and anti-HIV-1 activity evaluation of Keggin-type polyoxometalates with amino acid as organic cations" . | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 91 (2023) . |
| APA | Tian, Nana , Chu, Dongchen , Wang, Hongjun , Yan, Hong . Synthesis and anti-HIV-1 activity evaluation of Keggin-type polyoxometalates with amino acid as organic cations . | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 2023 , 91 . |
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Abstract ：
Epidermal growth factor receptor (EGFR) kinase is a promising target for the development of novel anticancer drugs. Based on the structure-activity relationships for the known inhibitors, 3,9-diazatetraasteranes have been developed as novel EGFR inhibitors. Molecular docking is performed for 3,9-diazatetraasteranes and the known inhibitor Erlotinib, and it suggests that 3,9-diazatetraasteranes are similar to Erlotinib in interactions with the catalytic sites of EGFR. A series of 3,9-diazatetraasteranes has been synthesized by photocyclization of 4-atyl-1,4-dihydropyridines, and their biological activity has been evaluated against A431 and HepG2 cell lines using Erlotinib as a control. Compound 1c exhibits the most potent antiproliferative activity against A431 (IC50 = 7.37 mu M) and HepG2 (IC50 = 9.81 mu M) cell lines compared to positive controls (IC50 = 8.92 mu M and 12.08 mu M). The results are indicating that 3,9-diazatetraasteranes may be the promising potential EGFR inhibitors.
Keyword ：
EGFR inhibitors EGFR inhibitors 3,9-diazatetraasteranes 3,9-diazatetraasteranes biological activities biological activities synthesis synthesis molecular docking molecular docking
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| GB/T 7714 | Mao, Li , Tian, Nana , Wei, Chaochun et al. Synthesis and Biological Activity of 3,9-Diazatetraasteranes as Novel EGFR Tyrosine Kinase Inhibitors [J]. | RUSSIAN JOURNAL OF GENERAL CHEMISTRY , 2022 , 92 (3) : 446-456 . |
| MLA | Mao, Li et al. "Synthesis and Biological Activity of 3,9-Diazatetraasteranes as Novel EGFR Tyrosine Kinase Inhibitors" . | RUSSIAN JOURNAL OF GENERAL CHEMISTRY 92 . 3 (2022) : 446-456 . |
| APA | Mao, Li , Tian, Nana , Wei, Chaochun , Wang, Hongjun , Yan, Hong . Synthesis and Biological Activity of 3,9-Diazatetraasteranes as Novel EGFR Tyrosine Kinase Inhibitors . | RUSSIAN JOURNAL OF GENERAL CHEMISTRY , 2022 , 92 (3) , 446-456 . |
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A series of pyrazolo[3,4-d]pyrimidin-4-one scaffold were designed and synthesized as novel CDK2 inhibitors. By analyzing the common motifs of various known inhibitors, the designed compounds 1 were virtually screen for their inhibitory activity by docking into the active pocket of CDK2. The influence of different substitutes on the docking results was investigated. A total of 15 pyrazolo[3,4-d]pyrimidin-4-ones 1 were synthesized by Paal-Knorr reaction, pyrimidine ring closure, bromination, Suzuki coupling reaction, amide formation and Knoevenagel condensation. The Cell Counting Kit-8 (CCK-8) was used to evaluate the inhibitory activity of pyrazolo[3,4-d]pyrimidin-4-ones 1 in the breast cancer cell line MCF-7 in vitro using Etoposide as a reference control substance. The screening results demonstrated that the designed compounds have significant antiproliferative activity, and compounds 1e and 1j were the most active compounds with IC50 values of 10.79 mu M and 10.88 mu M, respectively, being better than that of Etoposide (IC50 = 18.75 mu M). The enzyme inhibition assay was carried out against CDK2, the results indicated that the compounds 1e and 1j significantly inhibited CDK2 with IC50 values of 1.71 mu M and 1.60 mu M.
Keyword ：
Pyrazolo[3,4-d]pyrimidin-4-one Pyrazolo[3,4-d]pyrimidin-4-one Synthesis Synthesis Design Design CDK2 inhibitor CDK2 inhibitor Biological evaluation Biological evaluation
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| GB/T 7714 | Xie, Fan , Zhou, Liying , Ge, Changwei et al. Development of pyrazolo[3,4-d]pyrimidin-4-one scaffold as novel CDK2 inhibitors: Design, synthesis, and biological evaluation [J]. | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 2022 , 70 . |
| MLA | Xie, Fan et al. "Development of pyrazolo[3,4-d]pyrimidin-4-one scaffold as novel CDK2 inhibitors: Design, synthesis, and biological evaluation" . | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 70 (2022) . |
| APA | Xie, Fan , Zhou, Liying , Ge, Changwei , Song, Xiuqing , Yan, Hong . Development of pyrazolo[3,4-d]pyrimidin-4-one scaffold as novel CDK2 inhibitors: Design, synthesis, and biological evaluation . | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 2022 , 70 . |
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Abstract ：
In our research on novel anticancer agents, a series of N-6-hydrazone purine derivatives were designed and synthesized by analysis of a pharmacophore model for ATP-competitive inhibitors. The activities screening results showed that N-6-hydrazone purine derivatives 21 and 26 not only showed potential antiproliferative activity against the A549 and MCF-7 cell lines comparable to Vandetanib as a positive control but also had moderate antiplatelet aggregation activity. In order to investigate the possible targets, a molecular docking study was carried out on the fourteen kinases associated with anticancer and antiplatelet aggregation activities. The results indicated that compounds 21 and 26 had the potential activity to target VEGFR-2, PI3K alpha, EGFR, and HER2 kinases. The inhibition of the kinases assay showed that compound 26 could target VEGFR-2, PI3K alpha, and EGFR (IC50 = 0.822, 3.040 and 6.625 mu M). All results indicated that compound 26 will be an encouraging framework as potential new multi-target anticancer agent with potential antiplatelet aggregation activity.
Keyword ：
antiplatelet aggregation antiplatelet aggregation N-6-hydrazone derivatives of purine N-6-hydrazone derivatives of purine synthesis synthesis anticancer anticancer molecular docking molecular docking
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| GB/T 7714 | Wei, Chaochun , Zhou, Liying , Yang, Yifan et al. Design, synthesis, and anticancer evaluation of N-6-hydrazone purine derivatives with potential antiplatelet aggregation activity [J]. | CHEMICAL BIOLOGY & DRUG DESIGN , 2022 , 101 (3) : 568-580 . |
| MLA | Wei, Chaochun et al. "Design, synthesis, and anticancer evaluation of N-6-hydrazone purine derivatives with potential antiplatelet aggregation activity" . | CHEMICAL BIOLOGY & DRUG DESIGN 101 . 3 (2022) : 568-580 . |
| APA | Wei, Chaochun , Zhou, Liying , Yang, Yifan , Niu, Lexuan , Yan, Hong . Design, synthesis, and anticancer evaluation of N-6-hydrazone purine derivatives with potential antiplatelet aggregation activity . | CHEMICAL BIOLOGY & DRUG DESIGN , 2022 , 101 (3) , 568-580 . |
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