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学者姓名：闫红
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Abstract ：
Introduction SARS-CoV-2 pandemic has presented a significant threat to global health and the economy, necessitating urgent efforts to develop effective antiviral drugs. The main protease (3CLpro) of SARS-CoV-2 is a critical target for antiviral therapy due to its essential role in viral replication.Methods In order to find new structural types of 3CLpro inhibitors to facilitate the solution to the problem of new virus resistance. Six potential pharmacologically bioactive compounds were identified by utilizing structure-based virtual screening and in vitro assays from the Topscience database containing 10 million compounds.Results and Discussion Among these, compounds 34 and 36 exhibited potent inhibitory activity with IC50 values of 6.12 +/- 0.42 mu M and 4.47 +/- 0.39 mu M, respectively. To elucidate their binding mechanisms with 3CLpro, all-atom molecular dynamics (MD) simulations were conducted. Principal component analysis (PCA), free energy landscapes (FEL) and dynamic cross-correlation maps (DCCM) revealed that the binding of compounds 34 and 36 to 3CLpro significantly enhanced the structural stability of 3CLpro, reducing conformational flexibility and internal motions. The results of protein-ligand interaction showed that compounds 34 and 36 formed strong and stable interactions to key residues at active site of 3CLpro with different binding modes from S-217622. And HOMO-LUMO gap and molecular electrostatic potential distribution revealed the quantum chemical properties of compounds 34 and 36. These findings suggested that compounds 34 and 36 can be as novel SARS-CoV-2 3CLpro inhibitors and promising lead-like drug candidates for developing COVID-19 treatments.
Keyword ：
DFT DFT 3CLpro 3CLpro molecular docking molecular docking molecular dynamics molecular dynamics enzymatic assay enzymatic assay
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| GB/T 7714 | Zong, Keli , Wei, Chaochun , Li, Wei et al. Identification of novel SARS-CoV-2 3CLpro inhibitors by molecular docking, in vitro assays, molecular dynamics simulations and DFT analyses [J]. | FRONTIERS IN PHARMACOLOGY , 2024 , 15 . |
| MLA | Zong, Keli et al. "Identification of novel SARS-CoV-2 3CLpro inhibitors by molecular docking, in vitro assays, molecular dynamics simulations and DFT analyses" . | FRONTIERS IN PHARMACOLOGY 15 (2024) . |
| APA | Zong, Keli , Wei, Chaochun , Li, Wei , Ruan, Jiajun , Zhang, Susu , Li, Jingjing et al. Identification of novel SARS-CoV-2 3CLpro inhibitors by molecular docking, in vitro assays, molecular dynamics simulations and DFT analyses . | FRONTIERS IN PHARMACOLOGY , 2024 , 15 . |
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Abstract ：
C26H22BrN3O3, monoclinic, P21/c (no. 14), a = 17.7467(15) & Aring;, b = 10.7974(8) & Aring;, c = 11.9136(8) & Aring;, beta = 96.084 degrees, V = 2270.0(3) & Aring;3, Z = 4, Rgt(F) = 0.0375, wRref(F2) = 0.1205, T = 293 K.
Keyword ：
2350232 2350232
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| GB/T 7714 | Sun, Wuji , Sun, Lixin , Yan, Hong . Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3 [J]. | ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES , 2024 , 239 (4) : 763-765 . |
| MLA | Sun, Wuji et al. "Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3" . | ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES 239 . 4 (2024) : 763-765 . |
| APA | Sun, Wuji , Sun, Lixin , Yan, Hong . Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3 . | ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES , 2024 , 239 (4) , 763-765 . |
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Classical hydrocarbon scaffolds have long assisted in bringing new molecules to the market for a variety of applications, but one notable omission is that of tetraasteranes, which are homologues of cubanes belonging to a class of polycyclic hydrocarbon cage compounds. Tetraasteranes exhibit potential as scaffolds in drug discovery due to their identical cyclobutane structures and rigid conformation resembling cubanes. Based on the studies of the physical and chemical properties of tetraasteranes by density functional theory, three series of compounds were designed as homologues of cubanes by the substitution of cubane scaffolds in pharmaceuticals with tetraasteranes. Their potential for pharmaceutical applications was evaluated in silico by molecular docking and dynamics simulations. Their pharmacokinetic and physicochemical properties were studied by the ADMET (absorption, distribution, metabolism, excretion, and toxicity) analysis. The results indicate that tetraasteranes may be scaffolds as novel bioisosteres of cubanes, as well as hydrogen bond donors or acceptors, which enhance the affinity between ligands and receptors with more stable binding behavior and feasible tolerability in ADMET. All these findings provide new opportunities for tetraasteranes to serve as effective pharmaceutical scaffolds for drug discovery and to accelerate the drug discovery process by repurposing both new and old commercial compounds. An in silico study shows that polycyclic hydrocarbon cage compounds, tetraasteranes, can be effective scaffolds for drug discovery.
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| GB/T 7714 | Zhang, Xiaokun , Wei, Chaochun , Zong, Keli et al. Tetraasteranes as homologues of cubanes: effective scaffolds for drug discovery [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2024 , 22 (39) : 8037-8047 . |
| MLA | Zhang, Xiaokun et al. "Tetraasteranes as homologues of cubanes: effective scaffolds for drug discovery" . | ORGANIC & BIOMOLECULAR CHEMISTRY 22 . 39 (2024) : 8037-8047 . |
| APA | Zhang, Xiaokun , Wei, Chaochun , Zong, Keli , Zhong, Qidi , Yan, Hong . Tetraasteranes as homologues of cubanes: effective scaffolds for drug discovery . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2024 , 22 (39) , 8037-8047 . |
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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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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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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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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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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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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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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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