4-(4-Benzoylamino-phenyl)-butyric acid | 177653-17-7

• 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: 4-(4-Benzoylamino-phenyl)-butyric acid
• 英文别名: Benzenebutanoic acid, 4-(benzoylamino)-；4-(4-benzamidophenyl)butanoic acid
• CAS: 177653-17-7
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: ULVZWMUGKCFLMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(4-氨基苯基)丁酸 、 苯甲酰氯 在 sodium hydroxide 作用下， 反应 2.5h， 生成 4-(4-Benzoylamino-phenyl)-butyric acid
  参考文献：
  名称：

  4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric Acid as a Novel Oral Delivery Agent for Recombinant Human Growth Hormone

  摘要：

  A series of N-acetylated, non-alpha, aromatic amino acids was prepared and shown to promote the absorption of recombinant human growth hormone (rhGH) from the gastrointestinal tract. Seventy compounds in this family were tested in vivo in rats. Of the compounds tested, 4-[4-[(2-hydroxybenzoyl)amino]phenyl]butyric acid was identified as a preclinical candidate and was used to demonstrate the oral delivery of rhGH in primates. A significant positive correlation was found between the relative log k' of the delivery agents, as determined by HPLC on an immobilized artificial membrane (IAM) column, and serum rhGH concentrations following oral or colonic dosing in rats. Structure-activity relationships have also been developed on the basis of electronic effects and hydrogen-bonding characteristics of the aromatic amide substituents.

  DOI：

  10.1021/jm960038f

文献信息

• Method for administering GLP-1 molecules
  申请人：Emisphere Technologies, Inc.

  公开号：EP2409569A2

  公开（公告）日：2012-01-25

  The invention encompasses formulations that demonstrate the feasibility of oral absorption comprising GLP-1 compounds and specified delivery agents.

  本发明包括能证明口服吸收 GLP-1 化合物和特定给药剂可行性的制剂。
• Solution Phase Preparation of Highly Pure Amide Mixtures via In-Situ Chlorotrimethylsilane Protection and Activation
  作者：Koc-Kan Ho、Nai Fang Wang、Christine Lercara、Doris C. O'Toole、Douglas M. Achan、Edmund A. Vuocolo、Andrea Leone-Bay

  DOI：10.1080/00397919708004209

  日期：1997.3

  Coupling of 4-(4-aminophenyl)butyric acid 1 with acyl halides in both organic and aqueous media were found to produce large amount of oligomeric materials. By using an in situ chlorotrimethylsilane protection/activation procedure, these oligomers were suppressed completely and the desired 4-(4-acylaminophenyl)butyric acids 3 were obtained in good yield and high purity. The method was also extended to a parallel synthesis of a three component mixture. H-1-NMR of the mixture indicated that each component was formed in a nearly stoichiometric quantity.
• METHOD FOR ADMINISTERING GLP-1 MOLECULES
  申请人：Emisphere Technologies, Inc.

  公开号：EP1478233B1

  公开（公告）日：2016-11-09
• EP2409569B1
  申请人：——

  公开号：EP2409569B1

  公开（公告）日：2017-08-16
• US7939494B2
  申请人：——

  公开号：US7939494B2

  公开（公告）日：2011-05-10