• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
DAI Weiguo, TAN Hongzhou, GU Hongxia, HE Bing, HE Liqin, HUANG Peng. Design, synthesis and anti-platelet aggregation activity of paeonol oxime derivatives[J]. Journal of China Pharmaceutical University, 2022, 53(5): 535-541. DOI: 10.11665/j.issn.1000-5048.20220504
Citation: DAI Weiguo, TAN Hongzhou, GU Hongxia, HE Bing, HE Liqin, HUANG Peng. Design, synthesis and anti-platelet aggregation activity of paeonol oxime derivatives[J]. Journal of China Pharmaceutical University, 2022, 53(5): 535-541. DOI: 10.11665/j.issn.1000-5048.20220504

Design, synthesis and anti-platelet aggregation activity of paeonol oxime derivatives

Funds: This study was supported by the Natural Science Research Project for Colleges and Universities in Anhui Province (No.KJ2020A0957)
More Information
  • Received Date: May 23, 2022
  • Revised Date: September 20, 2022
  • In order to afford new antiplatelet agents with higher potency, a series of paeonol oxime derivatives (4a-4y) were designed and synthesized from paeonol.Their structures were confirmed by HRMS, 1H NMR spectra.The anti-platelet aggregation activity of the target compounds was evaluated.The results revealed that most of them had moderate to good anti-platelet aggregation activity.Among them, compound 4h and 4j were the most potent on adenosine diphosphate (ADP)-induced platelet aggregation and collagen-induced platelet aggregation. Furthermore, the target compound 4h not only showed strong antiplatelet aggregation activity, but also exhibited good water-solubility and drug-like properties, which can be used as a new antiplatelet active compound for further research.
  • [1]
    . Bioorg Med Chem,2005,13(21):5996-6001.
    [2]
    Saahene RO,Wang JJ,Wang ML,et al. The antitumor mechanism of paeonol on CXCL4/CXCR3-B signals in breast cancer through induction of tumor cell apoptosis[J]. Cancer Biother Radiopharm,2018,33(6):233-240.
    [3]
    Liao WY,Tsai TH,Ho TY,et al. Neuroprotective effect of paeonol mediates anti-inflammation via suppressing toll-like receptor 2 and toll-like receptor 4 signaling pathways in cerebral ischemia-reperfusion injured rats[J]. Evid Based Complement Alternat Med,2016,2016:3704647.
    [4]
    Zhao HL,Wang X,Liu SH,et al. Paeonol regulates NLRP3 inflammasomes and pyroptosis to alleviate spinal cord injury of rat[J]. BMC Neurosci,2022,23(1):16.
    [5]
    Wang QJ,Xu XM,Kang ZQ,et al. Paeonol prevents IL-1β-induced inflammatory response and degradation of type II collagen in human primary chondrocytes[J]. Artif Cells Nanomed Biotechnol,2019,47(1):2139-2145.
    [6]
    Li XL,Yang R,Yang XH,et al. Paeonol protects H9C2 cardiomyocytes from ischemia/reperfusion injury by activating Notch 1 signaling pathway in vitro[J]. Int J Clin Exp Med,2017,10(2):2866-2873.
    [7]
    Li W,Wang YL,Cai SX,et al. Effects of paeonol in comparison with aspirin on hemorrheological parameters in rats[J]. Chin Tradit Herb Drugs(中草药),2000,31(1):29-31.
    [8]
    Tsai CY,Kapoor M,Huang YP,et al. Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents[J]. Molecules,2016,21(2):145.
    [9]
    Huang TJ,Chuang H,Liang YC,et al. Design,synthesis,and bioevaluation of paeonol derivatives as potential anti-HBV agents[J]. Eur J Med Chem,2015,90:428-435.
    [10]
    Bai ZW,He LQ,Fang W. Synthesis and bioactivity of NO-donating paeonol derivatives[J]. Chem World(化学世界),2018,59(4):241-245.
    [11]
    Dai WG,Shang FY,Huang P,et al. Synthesis and antiplatelet aggregation activity of paeonol nitrate derivatives[J]. Chem World(化学世界),2021,62(4):219-223.
    [12]
    Bai ZW. Design,synthesis,and biological evaluation of paeonol derivatives(丹皮酚衍生物的设计、合成及生物活性研究)[D]. Hefei:Anhui University of Chinese Medicine,2018.
    [13]
    Rehse K,Brehme F. Azide oximes and 1-hydroxytetrazoles[J]. Arch Pharm Pharm Med Chem,2000,333(6):157-161.
    [14]
    Muri EMF,Barreiro EJ,Fraga CAM. Synthesis of new benzylic ethers of oximes derived from 1-phenyl-pyrazole compounds[J]. Synth Commun,1998,28(7):1299-1321.
    [15]
    Reil TD,Moore WS,Kashyap VS,et al. The effects of thrombus,thrombectomy and thrombolysis on endothelial function[J]. Eur J Vasc Endovasc Surg,2000,19(2):162-168.
    [16]
    Bai ZW,He LQ. Synthesis and anti-platelet aggregation activities of paeonol oxime ethers compounds[J]. Chem World(化学世界),2017,58(7):421-425.
    [17]
    Wang R,Ke JT,Sun H,et al. Synthesis and antiplatelet aggregation activity of peaonol oxime compounds[J]. Chem World(化学世界),2021,62(4):236-239.
    [18]
    Huang JK,He LQ,Huang P,et al. Synthesis and biological evaluation of aminoalcohol rheinate as anti-osteosarcoma agents[J]. Acta Pharm Sin(药学学报),2018,53(2):249-255.

Catalog

    Article views (306) PDF downloads (415) Cited by()

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return