3-[N-(4-methoxyphenyl)amino]benzoic acid | 852927-06-1

• 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-[N-(4-methoxyphenyl)amino]benzoic acid
• 英文别名: 3-[(4-methoxyphenyl)amino]benzoic acid；3-((4-Methoxyphenyl)amino)benzoic acid；3-(4-methoxyanilino)benzoic acid
• CAS: 852927-06-1
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: RAYGAWWVJQZVJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-甲氧基苯胺基)苯甲酸甲酯 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以76%的产率得到3-[N-(4-methoxyphenyl)amino]benzoic acid
  参考文献：
  名称：

  Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3)

  摘要：

  Aldo-keto reductase 1C3 (AKR1C3) also known as type 5 17 beta-hydroxysteroid dehydrogenase has been implicated as one of the key enzymes driving the elevated intratumoral androgen levels observed in castrate resistant prostate cancer (CRPC). AKR1C3 inhibition therefore presents a rational approach to managing CRPC. Inhibitors should be selective for AKR1C3 over other AKR1C enzymes involved in androgen metabolism. We have synthesized 2-, 3-, and 4-(phenylamino)benzoic acids and identified 3-(phenylamino) benzoic acids that have nanomolar affinity and exhibit over 200-fold selectivity for AKR1C3 versus other AKR1C isoforms. The AKR1C3 inhibitory potency of the 4'-substituted 3-(phenylamino)benzoic acids shows a linear correlation with both electronic effects of substituents and the pK(a) of the carboxylic acid and secondary amine groups, which are interdependent. These compounds may be useful in treatment and/or prevention of CRPC as well as understanding the role of AKR1C3 in endocrinology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.010

文献信息

• Nitroso derivatives of diphenylamine
  申请人：Lardy Claude

  公开号：US20070123586A1

  公开（公告）日：2007-05-31

  The invention relates to a compound of the formula I in which: R 1 represents, independently of each other, a halogen atom; an aliphatic hydrocarbon-based group optionally substituted and/or optionally interrupted by one or more oxygen or sulfur atoms; a nitro group; a cyano group; an amino group; a mono- or dialkylamino group; an alkylcarbonyl group; a carboxyl group; an alkylcarbonylamino group; an alkylsulfonyl group; R 2 represents, independently of each other, a cyano group; a hydroxyl group, an alkylcarbonyl group; a carboxyl group; an alkoxycarbonyl group; an unsubstituted amide group; or a linear or branched alkyl group substituted by a cyano, hydroxyl, carboxyl, alkoxycarbonyl or unsubstituted amide group; i and j independently being 1 to 5, with the exclusion of the compound for which i and j=1 and R 1 =carboxyl and R 2 =alkoxycarbonyl or R 1 =CF 3 and R 2 =carboxyl, and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.

  本发明涉及一种具有公式I的化合物，其中：R1分别表示卤素原子；一种基于脂肪族的羟基烃基团，可选地被一个或多个氧或硫原子取代和/或中断；硝基基团；氰基团；氨基团；一种单烷基或二烷基氨基团；烷基羰基基团；羧基团；烷基羰基氨基基团；烷基磺酰基基团；R2分别表示氰基团；羟基团；烷基羰基基团；羧基团；烷氧羰基基团；未取代酰胺基团；或线性或支链烷基团，被氰基，羟基，羧基，烷氧羰基或未取代酰胺基团取代；i和j分别独立地为1到5，除了i和j=1且R1=羧基和R2=烷氧羰基或R1=CF3和R2=羧基的化合物之外，还包括其药学上可接受的衍生物，盐，溶剂和立体异构体，包括所有比例的混合物。
• Diphenylamine derivatives
  申请人：Lardy Claude

  公开号：US20070129433A1

  公开（公告）日：2007-06-07

  The invention relates to compounds of the formula (I) in which: i and j=1; R 1 is in position 3 or 4 on the phenyl ring and represents a cyano group, an alkoxy group substituted by halogen, a thioalkyl group, an alkylcarbonyl group or an alkylsulfonyl group; and R 2 represents a carboxyl group, an aikoxycarbonyl group, an alkylcarbonyl group, an unsubstituted amide group or a linear or branched alkyl group substituted by a cyano, hydroxyl, cabboxyl, aikoxycarbonyl or unsubstituted amide group; and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.

  本发明涉及式(I)的化合物，其中：i和j=1；R1位于苯环上的3或4位置，并表示氰基，被卤素取代的烷氧基，硫代烷基，烷基羰基基团或烷基磺酰基团；R2表示羧基，烷氧羰基基团，烷基羰基基团，未取代酰胺基团或被氰基，羟基，羧基，烷氧羰基或未取代酰胺基团取代的线性或支链烷基；以及其药学上可接受的衍生物，盐，溶剂合物和立体异构体，包括所有比例的混合物。
• Bifunctional AKR1C3 Inhibitors/Androgen Receptor Modulators and Methods of Use Thereof
  申请人：The Trustees of The University of Pennsylvania

  公开号：US20140107085A1

  公开（公告）日：2014-04-17

  The invention includes compositions comprising selective AKR1C3 inhibitors. The invention also includes compositions comprising bifunctional AKR1C3 inhibitors and selective androgen receptor modulators. The invention further includes methods of treatment using the compositions of the invention.

  该发明包括含有选择性AKR1C3抑制剂的组合物。该发明还包括含有双功能AKR1C3抑制剂和选择性雄激素受体调节剂的组合物。该发明还包括使用该发明的组合物进行治疗的方法。
• Bifunctional AKR1C3 inhibitors/androgen receptor modulators and methods of use thereof
  申请人：The Trustees of the University of Pennsylvania

  公开号：US10071953B2

  公开（公告）日：2018-09-11

  The invention includes compositions comprising selective AKR1C3 inhibitors. The invention also includes compositions comprising bifunctional AKR1C3 inhibitors and selective androgen receptor modulators. The invention further includes methods of treatment using the compositions of the invention.

  本发明包括由选择性 AKR1C3 抑制剂组成的组合物。本发明还包括包含双功能 AKR1C3 抑制剂和选择性雄激素受体调节剂的组合物。本发明还包括使用本发明组合物的治疗方法。
• DIPHENYLAMINE DERIVATIVES
  申请人：Merk Patent Gmbh

  公开号：EP1687253A2

  公开（公告）日：2006-08-09