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

DAI Weiguo; TAN Hongzhou; GU Hongxia; HE Bing; HE Liqin; HUANG Peng

doi:10.11665/j.issn.1000-5048.20220504

Journal of China Pharmaceutical University > 2022 > 53(5): 535-541. > DOI: 10.11665/j.issn.1000-5048.20220504

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

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

1.
College of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012
2.
West Anhui Health Vocational College, Liuan 237005, China

Funds: This study was supported by the Natural Science Research Project for Colleges and Universities in Anhui Province (No.KJ2020A0957)

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Received Date: May 23, 2022
Revised Date: September 20, 2022

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Abstract

Abstract

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.
- peaonol oxime derivatives,
- synthesis,
- aqueous solubility,
- anti-platelet aggregation

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References (18)

References

[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.

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