4-(benzylamino)-2-hydroxybenzoic acid | 32484-16-5

• 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: 4-(benzylamino)-2-hydroxybenzoic acid
• 英文别名: 4-benzylamino-2-hydroxy-benzoic acid；4-Benzylamino-2-hydroxy-benzoesaeure；4-Benzylaminosalicylic acid
• CAS: 32484-16-5
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: DORGHVATGZQCJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛 、 4-氨基水杨酸 在 (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane 、 氢气 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、8.11 MPa 条件下， 反应 6.0h， 以47%的产率得到4-(benzylamino)-2-hydroxybenzoic acid
  参考文献：
  名称：

  使用 H2 的多取代胺与醛的主基团催化还原烷基化

  摘要：

  鉴于对绿色和可持续化学过程的需求不断增长，以低毒主族催化剂和分子氢为还原剂的胺的催化还原烷基化将是一种理想的胺官能化方法。然而，这样的过程仍然具有挑战性。在此，提出了一种使用 H2 的新型还原性烷基化系统，该系统通过串联反应进行，该反应涉及 B(2,6-Cl2C6H3)(p-HC6F4)2 催化形成亚胺，随后通过沮丧的刘易斯对（FLP）。这种还原性烷基化反应产生 H2O 作为唯一的副产物，并直接将带有广泛取代基的胺官能化，这些取代基包括羧基、羟基、附加氨基、伯酰胺和伯磺酰胺基团。异吲哚啉酮和氨基邻苯二甲酸酐的合成也已通过一锅法实现，该法分别由本发明的还原烷基化与分子内酰胺化和分子内脱水反应的组合组成。该反应分别显示出对亚胺中间体和 B(2,6-Cl2C6H3)(p-HC6F4)2 浓度的零级和一级依赖性。此外，H2 浓度显着影响反应进程。这些结果表明了一种可能的机制，其中包含 THF 和 B(2

  DOI：

  10.1021/jacs.8b03626

文献信息

• Pharmaceutical applications of hydrotropic agents, polymers thereof, and hydrogels thereof
  申请人：——

  公开号：US20030031715A1

  公开（公告）日：2003-02-13

  The present invention is directed to compounds effective for increasing the water solubility of poorly soluble drugs. Hydrotropic agents are identified, such as for increasing the solubility of paclitaxel. Polymerizable monomers of the hydrotropic agents are prepared and hydrotropic polymers formed from such monomers are generated. Both the monomers and resulting polymers increase the solubility of poorly soluble drugs. In some cases, the hydrotropic polymers are more effective at increasing solubility at low concentrations relative to a corresponding amount of the hydrotropic agent precursor. Additionally, the hydrotropic polymers (hytrops) can be crosslinked to yield hydrotropic hydrogels (hytrogels) capable of solubilizing a drug. The hytrogels can further be employed to generate micro- and nano-particle suspensions of a poorly soluble drug. The water solubility of paclitaxel can be increased by four orders of magnitude using compounds of the invention. Large molecular weight compounds, such as the hytrops and hytrogels, are expected to have low levels of absorption in the gastrointestinal tract, thereby making them particularly preferred for oral delivery of poorly soluble drugs.

  本发明涉及一种有效增加水溶性的难溶性药物的化合物。识别了亲水性剂，例如用于增加紫杉醇的溶解度。制备了亲水性剂的可聚合单体，并生成了由这些单体形成的亲水性聚合物。这些单体和最终产生的聚合物都可以增加难溶性药物的溶解度。在某些情况下，亲水性聚合物在低浓度下相对于相应量的亲水性剂前体更有效地增加溶解度。此外，亲水性聚合物（hytrops）可以交联以产生能够溶解药物的亲水性水凝胶（hytrogels）。这些hytrogels还可以用于生成难溶性药物的微米和纳米颗粒悬浮液。使用本发明的化合物，可以将紫杉醇的水溶性提高四个数量级。大分子量化合物，例如hytrops和hytrogels，预计在胃肠道中吸收水平较低，因此特别适用于口服难溶性药物的给药。
• Aumueller et al., Chemische Berichte, 1952, vol. 85, p. 760,772
  作者：Aumueller et al.

  DOI：——

  日期：——
• Some Derivatives of 4-Amino-2-hydroxybenzoic Acid (p-Aminosalicylic Acid)
  作者：Leonard Doub、J. J. Schaefer、L. L. Bambas、Constance T. Walker

  DOI：10.1021/ja01147a006

  日期：1951.3
• US7741352B2
  申请人：——

  公开号：US7741352B2

  公开（公告）日：2010-06-22
• [EN] PHARMACEUTICAL APPLICATIONS OF HYDROTROPIC AGENTS, POLYMERS THEREOF, AND HYDROGELS THEREOF<br/>[FR] APPLICATIONS PHARMACEUTIQUES D'AGENTS HYDROTROPES, POLYMERES ET HYDROGELS DE CES DERNIERS
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2002030466A2

  公开（公告）日：2002-04-18

  The present invention is directed to compounds effective for increasing the water solubility of poorly soluble drugs. Hydrotropic agents are identified, such as for increasing the solubility of paclitaxel. Polymerizable monomers of the hydrotropic agents are prepared and hydrotropic polymers formed from such monomers are generated. Both the monomers and resulting polymers increase the solubility of poorly soluble drugs. In some cases, the hydrotropic polymers are more effective at increasing solubility at low concentrations relative to a corresponding amount of the hydrotropic agent precursor. Additionally, the hydrotropic polymers (hytrops) can be crosslinked to yield hydrotropic hydrogels (hytrogels) capable of solubilizing a drug. The hytrogels can further be employed to generate micro-and nano-particle suspensions of a poorly soluble drug. The water solubility of paclitaxel can be increased by four orders of magnitude using compounds of the invention. Large molecular weight compounds, such as the hytrops and hytrogels, are expected to have low levels of absorption in the gastrointestinal tract, thereby making them particularly preferred for oral delivery of poorly soluble drugs.