3-(4-hydroxyphenyl)propionic acid propyl ester | 83281-52-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(4-hydroxyphenyl)propionic acid propyl ester
• 英文别名: n-propyl 3-(4-hydroxyphenyl)propionate；propyl 3-(4-hydroxyphenyl)propanoate
• CAS: 83281-52-1
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD24391534
• 分子量: 208.257
• InChiKey: QEOZPZMHUFEVEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)propionic acid propyl ester 在 Agaricus bisporus 、 氧气 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 24.0h， 以98%的产率得到3-(3,4-dihydroxyphenyl)propanoic acid propyl ester
  参考文献：
  名称：

  Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

  摘要：

  Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.026
• 作为产物：
  描述：

  丙醇 、 对羟基苯丙酸 在 3 A molecular sieve 、 硫酸 作用下， 反应 72.0h， 生成 3-(4-hydroxyphenyl)propionic acid propyl ester
  参考文献：
  名称：

  超短效β-肾上腺素受体阻断剂。2.在芳基官能团上含有酯的（芳氧基）丙醇胺。

  摘要：

  通过将酯官能团结合到某些（芳氧基）丙醇胺系统的芳基部分中，已经制备了几种短效β-肾上腺素能受体阻断剂。特别是，发现3- [4- [2-羟基-3-（异丙基氨基）丙氧基]苯基]丙酸甲酯盐酸盐（ASL-8052）是一种中度有效的心脏选择性化合物，当在以下条件下测定时具有短的作用时间体内犬模型。

  DOI：

  10.1021/jm00354a003

文献信息

• Method for treatment or prophylaxis of cardiac disorders
  申请人：American Hospital Supply Corporation

  公开号：US04387103A1

  公开（公告）日：1983-06-07

  A method for the treatment of prophylaxis of cardiac disorders in a mammal, comprising administering to such mammal a short-acting .beta.-blocking compound of the formula: ##STR1## wherein R may be lower alkyl, aryl, or aralkyl; n may be an integer from 0 to about 10; x may be an integer from 1 to 3; Ar may be substituted or unsubstituted aromatic; R.sub.1 may be lower alkyl, or aralkyl; and pharmaceutically accepted salts thereof. Novel compounds possessing short-acting .beta.-adrenergic blocking activity are also disclosed.

  一种用于治疗哺乳动物心脏疾病的预防的方法，包括向该类哺乳动物施用以下式的短效β-阻滞化合物：##STR1## 其中R可以是较低的烷基、芳基或芳基烷基；n可以是从0到约10的整数；x可以是从1到3的整数；Ar可以是取代或未取代的芳香基；R.sub.1可以是较低的烷基或芳基烷基；以及其药学上可接受的盐。还公开了具有短效β-肾上腺素能阻滞活性的新化合物。
• Compounds suitable for treatment or prophylaxis of cardiac disorders
  申请人：AMERICAN HOSPITAL SUPPLY CORPORATION

  公开号：EP0053435A1

  公开（公告）日：1982-06-09

  A method for the treatment or prophylaxis of cardiac disorders in a mammal, comprising administering to such mammal a short-acting β-blocking compound of the formula: wherein R may be lower alkyl, aryl, or aralkyl; n may be an integer from 0 to about 10; x may be an integer from 1 to 3; Ar may be substituted or unsubstituted aromatic; R, may be lower alkyl, or aralkyl; and pharmaceutically accepted salts thereof. Novel compounds possessing short acting β-adrenergic blocking activity are also disclosed.

  一种治疗或预防哺乳动物心脏疾病的方法，包括向哺乳动物施用式中的短效 β-阻断化合物： 其中 R 可以是低级烷基、芳基或烷基；n 可以是 0 至约 10 的整数；x 可以是 1 至 3 的整数；Ar 可以是取代或未取代的芳香族；R 可以是低级烷基或烷基；及其药学上可接受的盐类。还公开了具有短效β-肾上腺素能阻断活性的新型化合物。
• Ester derivatives of 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol as short-acting antiarrhythmic agents. 1
  作者：David M. Stout、Lawrence A. Black、Cynthia Barcelon-Yang、W. L. Matier、Barry S. Brown、Check Y. Quon、Herman F. Stampfli

  DOI：10.1021/jm00128a037

  日期：1989.8

  In an effort to find a replacement for the iv antiarrhythmic drug lidocaine having reduced systemic and central nervous system effects, activity against supraventricular as well as ventricular arrhythmias, and a biological half-life of less than 15 min, derivatives of the orally active class Ic clinical agent 2,6-bis(1-pyrrolidinylmethyl)-4-benzamidophenol, 1 (ACC-9358), were synthesized and tested. Compounds with ester groups attached to the phenyl ring were either weakly active or toxic. Replacement of the formanilide function with alkyl esters afforded compounds with antiarrhythmic activity in the range of 1. When the ester carboxyl was separated from the bis(aminomethyl)phenol by methylene units, very short half-lives were observed in human blood. In general, these compounds also had low lipophilic character.
• DE2735856
  申请人：——

  公开号：——

  公开（公告）日：——
• Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses
  作者：Giorgia Botta、Bruno Mattia Bizzarri、Adriana Garozzo、Rossella Timpanaro、Benedetta Bisignano、Donatella Amatore、Anna Teresa Palamara、Lucia Nencioni、Raffaele Saladino

  DOI：10.1016/j.bmc.2015.07.061

  日期：2015.9

  Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection. (C) 2015 Elsevier Ltd. All rights reserved.