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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 31859

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Prof. Dr. Jiang Wang

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State Key Laboratory of Drug Research, Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China
Interests: medicinal chemistry; drug design; discovery and development of metabolic novel drug; lead compound discovery and optimization; high efficient synthetic methodology; non-natural amino acid
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Prof. Dr. Liang-Ren Zhang

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State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
Interests: nucleosides and nucleotides; drug design and synthesis; molecular modeling
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Prof. Dr. Peng Zhan

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Key Laboratory of Chemical Biology (Ministry of Education), Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, 44 Wenhuaxi Road, Ji'nan 250012, China
Interests: antiviral drug; medicinal chemistry; drug design; new drug modalities
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Prof. Dr. Qi-Dong You

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State Key Laboratory of Natural Medicines and Jiangsu Key Laboratory of Drug Design and Optimization, China Pharmaceutical University, Nanjing 210009, China
Interests: design and synthesis of bioactive compound; synthesis and modification of natural product; drugability optimization
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Prof. Dr. Tian-Miao Ou

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School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
Interests: telomere; DNA; senescence; cancer biology; genome stability; molecular cell biology; RNA
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Prof. Dr. Xiao-Yun Lu

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School of Pharmacy, Jinan University, Guangzhou 510632, China
Interests: design and synthesis of bioactive compounds targeting lung disease; lung cancer; tuberculosis

Special Issue Information

Dear Colleagues,

This Special Issue is entitled “Medicinal Chemistry in China”. In China, many research groups, both from industry and academia, are working on medicinal chemistry topics that cover almost all therapeutic fields, ranging from metabolic disease, CNS disease, anticancer agents, and antiviral agents. Molecules devoted to the treatment of rare disease are also being investigated. The results obtained, frequently very important and recognized all over the world, are derived from the close collaboration of experts in different areas, such as computational chemistry, organic chemistry, biology, biochemistry, and pharmacology.

Scientists from China are cordially invited to contribute original research papers or reviews to this Special Issue of Molecules, which reports on the design, synthesis, and biological evaluation of potentially active compounds in the different subjects of medicinal chemistry.

Prof. Dr. Jiang Wang
Prof. Dr. Liang-Ren Zhang
Prof. Dr. Peng Zhan
Prof. Dr. Qi-Dong You
Prof. Dr. Tian-Miao Ou
Prof. Dr. Xiao-Yun Lu
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

drug design
drug discovery
lead compounds
anticancer agents
antiviral agents
antidiabetic agents
CNS agents

Related Special Issue

Medicinal Chemistry in Europe in Molecules (15 articles)

Published Papers (11 papers)

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Research

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20 pages, 7096 KiB

Open AccessArticle

Identification of Influenza PA_N Endonuclease Inhibitors via 3D-QSAR Modeling and Docking-Based Virtual Screening

by Chao Zhang, Junjie Xiang, Qian Xie, Jing Zhao, Hong Zhang, Erfang Huang, Pangchui Shaw, Xiaoping Liu and Chun Hu

Molecules 2021, 26(23), 7129; https://doi.org/10.3390/molecules26237129 - 25 Nov 2021

Cited by 5 | Viewed by 2178

Abstract

Structural and biochemical studies elucidate that PA_N may contribute to the host protein shutdown observed during influenza A infection. Thus, inhibition of the endonuclease activity of viral RdRP is an attractive approach for novel antiviral therapy. In order to envisage structurally diverse novel compounds with better efficacy as PA_N endonuclease inhibitors, a ligand-based-pharmacophore model was developed using 3D-QSAR pharmacophore generation (HypoGen algorithm) methodology in Discovery Studio. As the training set, 25 compounds were taken to generate a significant pharmacophore model. The selected pharmacophore Hypo1 was further validated by 12 compounds in the test set and was used as a query model for further screening of 1916 compounds containing 71 HIV-1 integrase inhibitors, 37 antibacterial inhibitors, 131 antiviral inhibitors and other 1677 approved drugs by the FDA. Then, six compounds (Hit01–Hit06) with estimated activity values less than 10 μM were subjected to ADMET study and toxicity assessment. Only one potential inhibitory ‘hit’ molecule (Hit01, raltegravir’s derivative) was further scrutinized by molecular docking analysis on the active site of PA_N endonuclease (PDB ID: 6E6W). Hit01 was utilized for designing novel potential PA_N endonuclease inhibitors through lead optimization, and then compounds were screened by pharmacophore Hypo1 and docking studies. Six raltegravir’s derivatives with significant estimated activity values and docking scores were obtained. Further, these results certainly do not confirm or indicate the seven compounds (Hit01, Hit07, Hit08, Hit09, Hit10, Hit11 and Hit12) have antiviral activity, and extensive wet-laboratory experimentation is needed to transmute these compounds into clinical drugs. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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12 pages, 1851 KiB

Open AccessArticle

Design, Synthesis, and Anticancer Activity Studies of Novel Quinoline-Chalcone Derivatives

by Yong-Feng Guan, Xiu-Juan Liu, Xin-Ying Yuan, Wen-Bo Liu, Yin-Ru Li, Guang-Xi Yu, Xin-Yi Tian, Yan-Bing Zhang, Jian Song, Wen Li and Sai-Yang Zhang

Molecules 2021, 26(16), 4899; https://doi.org/10.3390/molecules26164899 - 13 Aug 2021

Cited by 23 | Viewed by 2862

Abstract

The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC₅₀ values of 1.38, 5.34, and 5.21 µM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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23 pages, 8888 KiB

Open AccessArticle

Discovery of Novel Small-Molecule Inhibitors of PD-1/PD-L1 Interaction via Structural Simplification Strategy

by Hongbo Zhang, Yu Xia, Chunqiu Yu, Huijie Du, Jinchang Liu, Hui Li, Shihui Huang, Qihua Zhu, Yungen Xu and Yi Zou

Molecules 2021, 26(11), 3347; https://doi.org/10.3390/molecules26113347 - 02 Jun 2021

Cited by 17 | Viewed by 4060

Abstract

Blockade of the programmed cell death 1 (PD-1)/programmed cell death-ligand 1 (PD-L1) interaction is currently the focus in the field of cancer immunotherapy, and so far, several monoclonal antibodies (mAbs) have achieved encouraging outcomes in cancer treatment. Despite this achievement, mAbs-based therapies are struggling with limitations including poor tissue and tumor penetration, long half-life time, poor oral bioavailability, and expensive production costs, which prompted a shift towards the development of the small-molecule inhibitors of PD-1/PD-L1 pathways. Even though many small-molecule inhibitors targeting PD-1/PD-L1 interaction have been reported, their development lags behind the corresponding mAb, partly due to the challenges of developing drug-like small molecules. Herein, we report the discovery of a series of novel inhibitors targeting PD-1/PD-L1 interaction via structural simplification strategy by using BMS-1058 as a starting point. Among them, compound A9 stands out as the most promising candidate with excellent PD-L1 inhibitory activity (IC₅₀ = 0.93 nM, LE = 0.43) and high binding affinity to hPD-L1 (K_D = 3.64 nM, LE = 0.40). Furthermore, A9 can significantly promote the production of IFN-γ in a dose-dependent manner by rescuing PD-L1 mediated T-cell inhibition in Hep3B/OS-8/hPD-L1 and CD3-positive T cells co-culture assay. Taken together, these results suggest that A9 is a promising inhibitor of PD-1/PD-L1 interaction and is worthy for further study. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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15 pages, 4925 KiB

Open AccessArticle

Discovery and Biological Evaluation of CD147 N-Glycan Inhibitors: A New Direction in the Treatment of Tumor Metastasis

by Wenqian Li, Daojiong Wang, Yushu Ge, Lei Zhang, Jiang Wu and Dan Liu

Molecules 2021, 26(1), 33; https://doi.org/10.3390/molecules26010033 - 23 Dec 2020

Cited by 4 | Viewed by 2866

Abstract

N-glycosylation is instrumental to the regulation of CD147 functions, including the maturation of CD147, secretion of matrix metalloproteinases (MMPs), and promotion of tumor metastasis. Glycosylated CD147 is highly expressed in various cancer types, participates in metastasis, and is associated with the poor prognosis of malignant tumors. However, to date, there has been little development of target-specific inhibitors for CD147 glycosylation. In this work, we report a strategy for discovering CD147 glycosylation inhibitors through computer-aided screening and inhibition assays. Four compounds were screened as potential CD147 glycosylation inhibitors. Of these, compound 72 was finally identified as the best candidate. Further experiments confirmed that compound 72 inhibited the production of MMPs and the metastasis of cancer cells in the Hela cell line. Results further suggest that compound 72 could promote the expression of E-cadherin by targeting CD147, thereby inhibiting tumor migration. Finally, the structures of the other potential CD147 N-glycosylation inhibitors may eventually provide guidance for future optimization. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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23 pages, 9447 KiB

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Discovery of Novel Dual Extracellular Regulated Protein Kinases (ERK) and Phosphoinositide 3-Kinase (PI3K) Inhibitors as a Promising Strategy for Cancer Therapy

by Lingzhi Zhang, Qiurong Ju, Jinjin Sun, Lei Huang, Shiqi Wu, Shuping Wang, Yin Li, Zhe Guan, Qihua Zhu and Yungen Xu

Molecules 2020, 25(23), 5693; https://doi.org/10.3390/molecules25235693 - 03 Dec 2020

Cited by 5 | Viewed by 2371

Abstract

Concomitant inhibition of MAPK and PI3K signaling pathways has been recognized as a promising strategy for cancer therapy, which effectively overcomes the drug resistance of MAPK signaling pathway-related inhibitors. Herein, we report the scaffold-hopping generation of a series of 1H-pyrazolo[3,4-d]pyrimidine dual ERK/PI3K inhibitors. Compound 32d was the most promising candidate, with potent inhibitory activities against both ERK2 and PI3Kα which displays superior anti-proliferative profiles against HCT116 and HEC1B cancer cells. Meanwhile, compound 32d possessed acceptable pharmacokinetic profiles and showed more efficacious anti-tumor activity than GDDC-0980 and the corresponding drug combination (BVD-523 + GDDC-0980) in HCT-116 xenograft model, with a tumor growth inhibitory rate of 51% without causing observable toxic effects. All the results indicated that 32d was a highly effective anticancer compound and provided a promising basis for further optimization towards dual ERK/PI3K inhibitors. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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11 pages, 1292 KiB

Open AccessArticle

Preparation and Biological Evaluation of [^99mTc]Tc-CNGU as a PSMA-Targeted Radiotracer for the Imaging of Prostate Cancer

by Di Xiao, Xiaojiang Duan, Qianqian Gan, Xuran Zhang and Junbo Zhang

Molecules 2020, 25(23), 5548; https://doi.org/10.3390/molecules25235548 - 26 Nov 2020

Cited by 6 | Viewed by 2355

Abstract

Prostate-specific membrane antigen (PSMA) is a well-established biological target that is overexpressed on the surface of prostate cancer lesions. Radionuclide-labeled small-molecule PSMA inhibitors have been shown to be promising PSMA-specific agents for the diagnosis and therapy of prostate cancer. In this study, a glutamate-urea-based PSMA-targeted ligand containing an isonitrile (CNGU) was synthesized and labeled with ^99mTc to prepare [^99mTc]Tc-CNGU with a high radiochemical purity (RCP). The CNGU ligand showed a high affinity toward PSMA (K_i value is 8.79 nM) in LNCaP cells. The [^99mTc]Tc-CNGU exhibited a good stability in vitro and hydrophilicity (log P = −1.97 ± 0.03). In biodistribution studies, BALB/c nude mice bearing LNCaP xenografts showed that the complex had a high tumor uptake with 4.86 ± 1.19% ID/g, which decreased to 1.74 ± 0.90% ID/g after a pre-injection of the selective PSMA inhibitor ZJ-43, suggesting that it was a PSMA-specific agent. Micro-SPECT imaging demonstrated that the [^99mTc]Tc-CNGU had a tumor uptake and that the uptake was reduced in the image after blocking with ZJ-43, further confirming its PSMA specificity. All of the results in this work indicated that [^99mTc]Tc-CNGU is a promising PSMA-specific tracer for the imaging of prostate cancer. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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14 pages, 3359 KiB

Open AccessArticle

Synthesis and Biological Evaluation of Amino Chalcone Derivatives as Antiproliferative Agents

by Chao-Fan Lu, Sheng-Hui Wang, Xiao-Jing Pang, Ting Zhu, Hong-Li Li, Qing-Rong Li, Qian-Yu Li, Yu-Fan Gu, Zhao-Yang Mu, Min-Jie Jin, Yin-Ru Li, Yang-Yang Hu, Yan-Bing Zhang, Jian Song and Sai-Yang Zhang

Molecules 2020, 25(23), 5530; https://doi.org/10.3390/molecules25235530 - 25 Nov 2020

Cited by 20 | Viewed by 2924

Abstract

Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity of amino chalcone derivatives was studied in vitro and 5-Fu as a control group. Some of the compounds showed moderate to good activity against three human cancer cells (MGC-803, HCT-116 and MCF-7 cells) and compound 13e displayed the best antiproliferative activity against MGC-803 cells, HCT-116 cells and MCF-7 cells with IC₅₀ values of 1.52 μM (MGC-803), 1.83 μM (HCT-116) and 2.54 μM (MCF-7), respectively which was more potent than the positive control (5-Fu). Further mechanism studies were explored. The results of cell colony formatting assay suggested compound 10e inhibited the colony formation of MGC-803 cells. DAPI fluorescent staining and flow cytometry assay showed compound 13e induced MGC-803 cells apoptosis. Western blotting experiment indicated compound 13e induced cell apoptosis via the extrinsic/intrinsic apoptosis pathway in MGC-803 cells. Therefore, compound 13e might be a valuable lead compound as antiproliferative agents and amino chalcone derivatives worth further effort to improve amino chalcone derivatives’ potency. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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15 pages, 3791 KiB

Open AccessArticle

Design, Synthesis and Biological Evaluation of (2′,5′ and 3′5′-Linked) cGAMP Analogs that Activate Stimulator of Interferon Genes (STING)

by Xin Xie, Junyi Liu and Xiaowei Wang

Molecules 2020, 25(22), 5285; https://doi.org/10.3390/molecules25225285 - 12 Nov 2020

Cited by 8 | Viewed by 2805

Abstract

Stimulator of interferon genes (STING) is an endoplasmic reticulum adaptor transmembrane protein that plays a pivotal role in innate immune system. STING agonists, such as endogenous cyclic dinucleotide (CDN) cyclic GMP-AMP (cGAMP), have been used in diverse clinical research for immunogenic tumor clearance, antiviral treatments and vaccine adjuvants. CDNs containing noncanonical mixed 3′-5′ and 2′-5′ phosphodiester linkages show higher potency in the activation of the STING pathway. In this study, a series of 2′3′-CDNs were designed and synthesized through a modified one-pot strategy. We then established a surface plasmon resonance (SPR)-based binding assay to quantify the binding affinities of synthesized CDNs for human STING, which requested a minuscule amount of sample without any pretreatment. Using this assay, we identified compound 8d (K_D = 0.038 μM), a novel CDN that showed higher binding affinity with hSTING than cGAMP (K_D = 0.543 μM). Cellular assays confirmed that 8d could trigger the expression of type I IFNs and other proinflammatory cytokines more robust than cGAMP. 8d also exhibited more resistant than cGAMP to enzymatic cleavage in vitro, indicating the successful improvement in drug availability. These findings provide guidelines for the design and structural optimization of CDNs as STING agonists. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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18 pages, 2262 KiB

Open AccessArticle

(5-Hydroxy-4-oxo-2-styryl-4H-pyridin-1-yl)-acetic Acid Derivatives as Multifunctional Aldose Reductase Inhibitors

by Huan Chen, Xin Zhang, Xiaonan Zhang, Wenchao Liu, Yanqi Lei, Changjin Zhu and Bing Ma

Molecules 2020, 25(21), 5135; https://doi.org/10.3390/molecules25215135 - 04 Nov 2020

Cited by 7 | Viewed by 2217

Abstract

As rate-limited enzyme of polyol pathway, aldose reductase (ALR2) is one of the key inhibitory targets for alleviating diabetic complications. To reduce the toxic side effects of the inhibitors and to decrease the level of oxidative stress, the inhibitory selectivity towards ALR2 against detoxicating aldehyde reductase (ALR1) and antioxidant activity are included in the design of multifunctional ALR2 inhibitors. Hydroxypyridinone derivatives were designed, synthesized and evaluated their inhibitory behavior and antioxidant activity. Notably, {2-[2-(3,4-dihydroxy-phenyl)-vinyl]-5-hydroxy-4-oxo-4H-pyridin-1-yl}-acetic acid (7l) was the most potent, with IC₅₀ values of 0.789 μM. Moreover, 7l showed excellent selectivity towards ALR2 with selectivity index 25.23, which was much higher than that of eparlestat (17.37), the positive control. More significantly, 7l performed powerful antioxidative action. At a concentration of 1 μM, phenolic compounds 7l scavenged DPPH radical with an inhibitory rate of 41.48%, which was much higher than that of the well-known antioxidant Trolox, at 11.89%. Besides, 7l remarkably suppressed lipid peroxidation with a rate of 88.76% at a concentration of 100 μM. The binding mode derived from molecular docking proved that the derivatives were tightly bound to the activate site, suggesting strongly inhibitory action of derivatives against ALR2. Therefore, these results provided an achievement of multifunctional ALR2 inhibitors capable with potency for both selective ALR2 inhibition and as antioxidants. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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16 pages, 3066 KiB

Open AccessArticle

Andrographolide and Its 14-Aryloxy Analogues Inhibit Zika and Dengue Virus Infection

by Feng Li, Wipaporn Khanom, Xia Sun, Atchara Paemanee, Sittiruk Roytrakul, Decai Wang, Duncan R. Smith and Guo-Chun Zhou

Molecules 2020, 25(21), 5037; https://doi.org/10.3390/molecules25215037 - 30 Oct 2020

Cited by 20 | Viewed by 2832

Abstract

Andrographolide is a labdene diterpenoid with potential applications against a number of viruses, including the mosquito-transmitted dengue virus (DENV). In this study, we evaluated the anti-viral activity of three 14-aryloxy analogues (ZAD-1 to ZAD-3) of andrographolide against Zika virus (ZIKV) and DENV. Interestingly, one analogue, ZAD-1, showed better activity against both ZIKV and DENV than the parental andrographolide. A two-dimension (2D) proteomic analysis of human A549 cells treated with ZAD-1 compared to cells treated with andrographolide identified four differentially expressed proteins (heat shock 70 kDa protein 1 (HSPA1A), phosphoglycerate kinase 1 (PGK1), transketolase (TKT) and GTP-binding nuclear protein Ran (Ran)). Western blot analysis confirmed that ZAD-1 treatment downregulated expression of HSPA1A and upregulated expression of PGK1 as compared to andrographolide treatment. These results suggest that 14-aryloxy analogues of andrographolide have the potential for further development as anti-DENV and anti-ZIKV agents. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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Review

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18 pages, 764 KiB

Open AccessReview

Secondary Metabolites and Their Bioactivities Produced by Paecilomyces

by Ze-Bao Dai, Xin Wang and Guo-Hong Li

Molecules 2020, 25(21), 5077; https://doi.org/10.3390/molecules25215077 - 01 Nov 2020

Cited by 20 | Viewed by 3117

Abstract

Paecilomyces, a common saprobic filamentous fungus, not only plays an important role in biological control, but also has applications in medicine, food, and environmental protection. In this paper, 223 secondary metabolites and their bioactivities from 13 known species and various unidentified strains of Paecilomyces are reviewed. Their structures can be described as polyketide, terpenoid, peptide, alkaloid, quinone, pyrone, sterol, and fatty acid. They have been demonstrated varying biological activities, including antimicrobial, antitumor, insecticidal, antiplasmodial, antimalarial, nematicidal, herbicidal, and enzyme-inhibiting. This review provides a comprehensive overview of secondary metabolites and their biological activities from strains of Paecilomyces. Full article

(This article belongs to the Special Issue Medicinal Chemistry in China)

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