3-(2-acetoxybenzamido)propanoic acid | 161992-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-acetoxybenzamido)propanoic acid
• 英文别名: o-acetoxy-N-benzoyl-β-alanine；3-[(2-Acetyloxybenzoyl)amino]propanoic acid
• CAS: 161992-97-8
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: FLEVCNLUTPGAEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-acetoxybenzamido)propanoic acid 在 sodium hydroxide 作用下， 反应 2.0h， 生成 N-salicyloyl-β-alanine
  参考文献：
  名称：

  Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin

  摘要：

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.

  DOI：

  10.1021/jm970811m
• 作为产物：
  描述：

  β-alanine trimethylsilyl ester 、 邻乙酰水杨酰氯 在 三乙胺 作用下， 生成 3-(2-acetoxybenzamido)propanoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin

  摘要：

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.

  DOI：

  10.1021/jm970811m

文献信息

• Modeling of Controlled Release of Aspirin Derivatives from Human Erythrocytes.
  作者：Masahiko OHSAKO、Yasuhiro OKA、Osami TSUZUKI、Yasuhiro MATSUMOTO

  DOI：10.1248/bpb.18.310

  日期：——

  binding positions, the hydrolyzed derivatives were released rapidly in the order of p- > m- > o-AcOHBA (ASP). The rates of derivatives were accelerated by lengthening of the side chain of the acetoxyl group (BuOHBA > PrOHBA > ASP). The rate of release of o-, m- or p-AcOHBA, BuOHBA and PrOHBA was related to hydrolysis rate in erythrocytes but not to partition coefficient (log P). In different amino acids

  阿司匹林（ASP）及其衍生物（间或对乙酰氧基苯甲酸（间或对AcOHBA），邻丙酰氧基苯甲酸（PrOHBA），邻丁酰氧基苯甲酸（BuOHBA），邻乙酰氧马尿酸（AcOHPA）的运输，并通过人红细胞膜研究了邻乙酰氧基-N-苯甲酰基-β-丙氨酸（AcONBA）。尽管ASP衍生物的转运速率有所不同，但它们被转运到红细胞中，然后被水解然后释放。在不同的结合位置，水解的衍生物以p-> m-> o-AcOHBA（ASP）的顺序快速释放。通过延长乙酰氧基基团的侧链（BuOHBA> PrOHBA> ASP），可以加快衍生物的转化率。o-，间-或对-AcOHBA的释放速率，BuOHBA和PrOHBA与红细胞中的水解速率有关，但与分配系数无关（log P）。在ASP羧基的不同氨基酸中，AcONBA的释放较慢，需要大约2小时才能达到平衡。在孵育3小时后，AcOHPA的释放也较慢并逐渐增加。AcOHPA和AcONB
• Synthesis and biological evaluation of the codrug of Leonurine and Aspirin as cardioprotective agents
  作者：Huan Gao、Xiaohong Yang、Xianfeng Gu、Yi-Zhun Zhu

  DOI：10.1016/j.bmcl.2016.08.058

  日期：2016.10

  The novel codrugs of Leonurine and Aspirin, compounds 545 and 503 have been synthesized and evaluated on their cardioprotective effects. Preliminary pharmacological studies showed that both compounds 545 and 503 were able to increase cell viability of hypoxia-induced H9c2 cells, and compound 545 exhibited at least ten fold potency than 503 and their parent drugs (Leonurine and Aspirin). Further mechanisms

  合成了Leururine和Aspirin的新型前药化合物545和503，并对其心脏保护作用进行了评估。初步的药理研究表明，化合物545和503均能增加缺氧诱导的H9c2细胞的细胞活力，并且化合物545的功效至少比503及其母体药物（利尿氨酸和阿司匹林）高十倍。进一步的机制研究表明545的心脏保护作用是由于其（1）通过增加SOD和CAT酶的活性以及降低MDA含量和LDH漏出率的抗氧化能力，（2）通过调节凋亡相关蛋白的表达的抗凋亡活性。在缺氧期间，（3）通过抑制促炎性介质发挥抗炎作用。
• 益母草碱与阿司匹林缀合物的制备方法
  申请人：复旦大学

  公开号：CN106146355B

  公开（公告）日：2018-02-27

  本发明属于药物化学领域，涉及益母草碱‑阿司匹林缀合物的合成方法。本发明以丁香酸、S‑甲基异硫脲和阿司匹林为起始原料，分别经乙酰化、BOC保护、酰胺化以及去乙酰化等反应，得到相应结构片段，最后采用二异丙基碳酰亚胺、4‑二甲氨基吡啶和4‑甲基苯磺酸合用作为缩合催化剂将三个片段进行连接，三氟乙酸脱BOC保护得到目标化合物。本发明方法操作简便，条件温和，后处理简单，能提高中间体益母草碱产品收率；制得的益母草碱‑阿司匹林缀合物，总收率25.27％，经药理活性测试，结果表明其在细胞水平上具有很好的抗氧化、抗凋亡作用，对心肌细胞保护作用确切。
• Pegylated Ion Channel Modulating Compounds
  申请人：Cheu L.S. Elizabeth

  公开号：US20080021005A1

  公开（公告）日：2008-01-24

  This invention is directed to PEGlyated derivatives, drug conjugates and isotopic derivatives of certain ion channel modulating compounds. Pharmaceutical compositions and methods of use of also disclosed

  这项发明是针对某些离子通道调节化合物的PEG化衍生物、药物偶联物和同位素衍生物。还公开了制药组合物和使用方法。
• PEGYLATED ION CHANNEL MODULATING COMPOUNDS
  申请人：Cheu Elizabeth L. S.

  公开号：US20100273724A1

  公开（公告）日：2010-10-28

  This invention is directed to PEGlyated derivatives, drug conjugates and isotopic derivatives of certain ion channel modulating compounds. Pharmaceutical compositions and methods of use of also disclosed

  这项发明涉及某些离子通道调节化合物的PEG化衍生物、药物结合物和同位素衍生物。还公开了制药组合物和使用方法。