Design, synthesis and evaluation of nitric oxide releasing derivatives of 3-n-butylphthalide as antiplatelet and antithrombotic agents

Xuliang Wang; Yang Li; Qian Zhao; Zhenli Min; Chao Zhang; Yisheng Lai; Hui Ji; Sixun Peng; Yihua Zhang

doi:10.1039/C1OB05478C

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Organic & Biomolecular Chemistry

Issue 16, 2011

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Design, synthesis and evaluation of nitric oxide releasing derivatives of 3-n-butylphthalide as antiplatelet and antithrombotic agents

Xuliang Wang , Yang Li , Qian Zhao , Zhenli Min , Chao Zhang , Yisheng Lai , Hui Ji , Sixun Peng and Yihua Zhang

Org. Biomol. Chem., 2011,9, 5670-5681

DOI: 10.1039/C1OB05478C
Received 26 Mar 2011, Accepted 12 Apr 2011
First published on the web 12 Apr 2011

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Novel nitric oxide (NO) releasing derivatives (7a–7l) of 3-n-butylphthalide (NBP) were designed and synthesized. Compound 7e inhibited the adenosine diphosphate (ADP), thrombin (TH) and arachidonic acid (AA)-induced in vitro platelet aggregation, superior to NBP and aspirin, released moderate levels of NO, and improved aqueous solubility relative to NBP. Furthermore, 7e exhibited greater antithrombotic activity than NBP and aspirin in rats, and protected against collagen and adrenaline-induced thrombosis in mice. Therefore, NO-releasing NBP derivatives possessed potent antiplatelet aggregation and antithrombotic activity. Our findings may aid in the design of new therapeutic agents for the treatment of thrombosis-related ischemic stroke.