CAS: 380905-48-6; 2-(1-Hydroxypentyl)Benzoic Acid

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    butylphthalide 6-(1-hydroxy-pentyl)-cyclohex-1-enecarboxylic acid 2-(1-hydroxy-pentyl)-cyclohex-2-enecarboxylic acid phthalic anhydridebenzene-1,2-dicarboxylic acid (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester (+/-)-(E)-2-methoxy-4-(3-(4-(nitrooxy)butoxy)-3-oxoprop-1-en-1-yl)phenyl 2-(1-(2-chloroacetoxy)pentyl)benzoate (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester

    合成工艺路线路线简述

      📜3-丁基-1(3H)-异苯并呋喃酮置于sodium Hydroxide,盐酸体系中,用 甲醇,水 作为反应溶剂,化学反应 0.5H,反应生成 丁苯酞杂质
      参考文献:Studies On The Enantiomers Of Zjm-289: Synthesis And Biological Evaluation Of Antiplatelet,Antithrombotic And Neuroprotective Activities
      标题:Studies On The Enantiomers Of Zjm-289: Synthesis And Biological Evaluation Of Antiplatelet,Antithrombotic And Neuroprotective Activities
      摘要:Zjm-289是一种强效的外消旋剂,其在抑制血小板聚集和血栓形成方面优于已知的抗缺血性脑卒药物3-N-丁基苯酞(Nbp).在此,合成了zjm-289的两种对映体,即(S)-Zjm-289和(R)-Zjm-289,并对其生物活性进行了评估.观测到这两种对映体在抑制体外血小板聚集和体内血栓形成方面几乎与zjm-289同样有效.此外,与zjm-289类似,其对映体能够调节血栓素b2(Txb2)和6-酮前列腺素f1α的比例,并增强一氧化氮(No),Camp和cgmp的水平,这表明对映体和zjm-289的抗血小板和抗血栓活性与花生四烯酸级联反应和cgmp-No信号通路有关.进一步发现,口服对映体和zjm-289三天显著减少了脑缺血再灌注后大鼠的脑梗死面积,脑含水量和神经功能缺损.重要的是,这两种对映体同样改善了缺血性脑卒模型中的血流,并通过释放适度的no来调节内皮功能,这可能至少部分地促使其神经保护作用.总之,本研究表明,两种对映体在抑制血小板聚集和血栓形成以及神经保护方面与zjm-289同样强效,并且在某些情况下,(S)-Zjm-289显示出比(R)-Zjm-289和zjm-289更好的效果.这些发现可能为开发类似于zjm-289的治疗血栓相关缺血性脑卒的药物提供新的见解.
      DOI:10.1039/c2Ob26511G

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      专利信息


      专利号:US-12403116-B2
      优先权日:2022-03-04
      标 题:Hydroxypentyl benzoic acid diester compound, and preparation method and pharmaceutical application thereof
      发明人:SUN XIAOBO; TIAN YU; SUN XIAO
      权利人:CHINESE ACADEMY OF MEDICAL SCIENCES INST OF MEDICINAL PLANT DEVELOPMENT
      摘要:Disclosed are a hydroxypentyl benzoic acid diester compound, a method preparing the same, and an application of the same. This application uses a combination principle, on the one hand, the medicine concentration of butylphthalide in cerebral vessels is improved through a function of promoting the medicine to penetrate through a blood-brain barrier of dexborneol, and a multi-target multi-channel synergistic brain protection effect of the medicine is exerted; on the other hand, the treatment effect of dexborneol on cerebral ischemia is exerted. Anti-cerebral ischemia in-vivo pharmacodynamic activity evaluation is carried out on the synthesized compound, a high-activity candidate medicine is obtained, and industrial production can be achieved through the synthesis method.

      专利号:CN-117229144-A
      优先权日:2023-09-18
      标题:A kind of synthesis technology of butylphthalide derivatives

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      合成参考文献


      参考文献:10.1124/jpet.105.098517
      摘要:Zhang Y, Wang L, Li J, Wang X. 2-(1-Hydroxypentyl)-benzoate Increases Cerebral Blood Flow and Reduces Infarct Volume in Rats Model of Transient Focal Cerebral Ischemia. The Journal of Pharmacology and Experimental Therapeutics. 2006 Jun;317(3):973–9. doi: 10.1124/jpet.105.098517.
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