(R)-2-(1-acetoxy-n-pentyl)benzoic acid | 1428866-34-5

• 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: (R)-2-(1-acetoxy-n-pentyl)benzoic acid
• 英文别名: 2-[(1R)-1-acetyloxypentyl]benzoic acid
• CAS: 1428866-34-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: WOLLRQSMWVBXJO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(1-acetoxy-n-pentyl)benzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 R-2-(1-acetoxy-n-pentyl)benzoyl chloride
  参考文献：
  名称：

  R-或S-2-(1-乙酰氧正戊基)苯甲酸与4-氟-依达拉奉的杂合物及其制备与应用

  摘要：

  本发明公开了R‑或S‑2‑(1‑乙酰氧正戊基)苯甲酸与4‑氟‑依达拉奉的杂合物(R‑或S‑FMPB)的制备方法及其用途，本发明的优选化合物S‑FMPB具有前体药物的基本特征，在体内可快速代谢并释放出可协同作用的S‑丁苯酞和4‑氟‑依达拉奉两个活性片段，展示了较RS‑和R‑FMPB更显著的抗急性缺血性脑卒中活性。S‑FMPB的疗效不仅优于等摩尔的S‑2‑(1‑乙酰氧正戊基)苯甲酸和4‑氟‑依达拉奉单独或联合给药，而且优于临床常用的丁苯酞与依达拉奉联合用药的效果。此外，S‑FMPB具有较高的体外稳定性及良好的体内药代动力学性质。

  公开号：

  CN115160227A
• 作为产物：
  描述：

  3-丁基-1(3H)-异苯并呋喃酮 在 甲醇 、 4-二甲氨基吡啶 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (R)-2-(1-acetoxy-n-pentyl)benzoic acid
  参考文献：
  名称：

  R-或S-2-(1-乙酰氧正戊基)苯甲酸与4-氟-依达拉奉的杂合物及其制备与应用

  摘要：

  本发明公开了R‑或S‑2‑(1‑乙酰氧正戊基)苯甲酸与4‑氟‑依达拉奉的杂合物(R‑或S‑FMPB)的制备方法及其用途，本发明的优选化合物S‑FMPB具有前体药物的基本特征，在体内可快速代谢并释放出可协同作用的S‑丁苯酞和4‑氟‑依达拉奉两个活性片段，展示了较RS‑和R‑FMPB更显著的抗急性缺血性脑卒中活性。S‑FMPB的疗效不仅优于等摩尔的S‑2‑(1‑乙酰氧正戊基)苯甲酸和4‑氟‑依达拉奉单独或联合给药，而且优于临床常用的丁苯酞与依达拉奉联合用药的效果。此外，S‑FMPB具有较高的体外稳定性及良好的体内药代动力学性质。

  公开号：

  CN115160227A

文献信息

• 2-(1-酰氧正戊基)苯甲酸与碱性氨基酸或氨基胍形成的盐、其制备方法及用途
  申请人：中国药科大学

  公开号：CN109678715A

  公开（公告）日：2019-04-26

  本发明公开了一种2‑(1‑酰氧正戊基)苯甲酸与碱性氨基酸或氨基胍形成的盐、其制备方法、含有这些盐的药物制剂，及其在制备预防或治疗心脑缺血性疾病、抗血栓、改善心脑循环障碍药物中的应用。本发明的化合物不仅具有优良的水溶性、水溶液稳定性及药代动力学性质，还具有强效的抗血小板聚集、抗血栓、抗脑缺血以及保护神经的活性，效果优于(S)‑丁苯酞和(R/S)‑2‑(1‑羟基正戊基)苯甲酸钾盐(PHPB)，并且本发明化合物对小鼠静脉注射给药的急性毒性显著小于丁苯酞和PHPB，对CHO‑hERG细胞hERG钾通道的抑制率低于(S)‑丁苯酞，微生物回复突变试验(Ames试验)的结果为阴性。
• 2-(1-ACYLOXYPENTYL) BENZOIC ACID SALT FORMED BY BASIC AMINO ACID OR AMINOGUANIDINE, PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：China Pharmaceutical University

  公开号：EP3838887A1

  公开（公告）日：2021-06-23

  The present disclosure discloses salts formed by 2-(1-acyloxy-n-pentyl)benzoic acid and basic amino acid or aminoguanidine, a preparation method thereof, pharmaceutical preparations containing these salts, and application thereof in preparation of drugs for preventing or treating ischemic cardiovascular and cerebrovascular diseases, resisting thrombosis and improving cardio-cerebral circulation disorders. The compound of the present disclosure has excellent water solubility, aqueous solution stability and pharmacokinetic properties, also has significant anti-platelet aggregation, anti-thrombosis, anti-cerebral ischemia and neuroprotective activity. The compound of the present disclosure has significantly better effects than those of (S)-butylphthalide and potassium (R/S)-2-(1-hydroxy-n-pentyl) benzoate (PHPB), has significantly lower acute toxicity to mice by intravenous injection than that of butylphthalide and PHPB, has a lower inhibition rate of the hERG potassium channel in CHO-hERG cells than that of (S)-butylphthalide, and has a negative result in Bacterial Reverse Mutation Test (Ames test).

  本发明公开了2-(1-乙酰氧基-n-戊基)苯甲酸与碱性氨基酸或氨基胍形成的盐、其制备方法、含有这些盐的药物制剂，以及其在制备预防或治疗缺血性心脑血管疾病、抗血栓形成和改善心脑循环障碍药物中的应用。本公开的化合物具有优异的水溶性、水溶液稳定性和药代动力学特性，还具有显著的抗血小板聚集、抗血栓形成、抗脑缺血和神经保护活性。与(S)-丁基苯酞和(R/S)-2-(1-羟基-n-戊基)苯甲酸钾（PHPB）相比，本公开的化合物具有明显更好的效果，静脉注射对小鼠的急性毒性明显低于丁基苯酞和 PHPB、在 CHO-hERG 细胞中对 hERG 钾通道的抑制率低于(S)-丁基苯酞，并且在细菌反向突变试验（Ames 试验）中呈阴性结果。
• Novel Hybrids of Optically Active Ring-Opened 3-<i>n</i>-Butylphthalide Derivative and Isosorbide as Potential Anti-Ischemic Stroke Agents
  作者：Xiaoli Wang、Linna Wang、Tingting Li、Zhangjian Huang、Yisheng Lai、Hui Ji、Xiaolong Wan、Jinyi Xu、Jide Tian、Yihua Zhang

  DOI：10.1021/jm4001693

  日期：2013.4.11

  In search of novel anti-ischemic stroke agents with higher potency than a known drug 3-n-butylphthalide (NBP), a series of hybrids ((S)- and (R)-5a-f) from optically active ring-opened NBP derivative and isosorbide were synthesized for evaluating their anti-ischemic stroke activity. Compound (S)-5e displayed the strongest activity in inhibiting the adenosine diphosphate (ADP) and arachidonic acid (AA)-induced platelet aggregation in vitro, with 10.0- and 8.4-fold more effectiveness than (S)-NBP, respectively. Furthermore, (S)-5e was stable in artificial gastrointestinal fluids and could penetrate the blood-brain barrier (BBB) with an appreciate lipid/water partition coefficient relative to (S)-NBP. More importantly, oral treatment with (S)-5e protected from acute thrombosis and inhibited the ischemia/reperfusion-related brain injury in animals. Our findings suggest that (S)-5e may be promising for further evaluation for the intervention of ischemic stroke.
• SALTS FORMED BY 2-(1-ACYLOXY-N-PENTYL) BENZOIC ACID AND BASIC AMINO ACID OR AMINOGUANIDINE, AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：CHINA PHARMACEUTICAL UNIVERSITY

  公开号：US20220024848A1

  公开（公告）日：2022-01-27

  The present disclosure discloses salts formed by 2-(1-acyloxy-n-pentyl)benzoic acid and basic amino acid or aminoguanidine, a preparation method thereof, pharmaceutical preparations containing these salts, and application thereof in preparation of drugs for preventing or treating ischemic cardiovascular and cerebrovascular diseases, resisting thrombosis and improving cardio-cerebral circulation disorders. The compound of the present disclosure has excellent water solubility, aqueous solution stability and pharmacokinetic properties, also has significant anti-platelet aggregation, anti-thrombosis, anti-cerebral ischemia and neuroprotective activity. The compound of the present disclosure has significantly better effects than those of (S)-butylphthalide and potassium (R/S)-2-(1-hydroxy-n-pentyl) benzoate (PHPB), has significantly lower acute toxicity to mice by intravenous injection than that of butylphthalide and PHPB, has a lower inhibition rate of the hERG potassium channel in CHO-hERG cells than that of (S)-butylphthalide, and has a negative result in Bacterial Reverse Mutation Test (Ames test).