3-氨基-4-苯基氨基苯甲酸 | 55296-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-4-苯基氨基苯甲酸
• 英文名称: 3-amino-4-(phenylamino)benzoic acid
• 英文别名: 3-amino-4-phenylaminobenzoic acid；3-amino-4-anilino-benzoic acid；2-Amino-diphenylamin-carbonsaeure-(4)；3-Amino-4-anilino-benzoesaeure；3-amino-4-phenylamino-benzoic acid；3-amino-4-anilinobenzoic acid
• CAS: 55296-17-8
• 化学式: C₁₃H₁₂N₂O₂
• mdl: MFCD00450821
• 分子量: 228.25
• InChiKey: SOSRJZNYVRVFOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  3-氨基-4-苯基氨基苯甲酸 生成 邻氨基二苯胺
  参考文献：
  名称：

  Schoepff, Chemische Berichte, 1889, vol. 22, p. 3287

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 铜 作用下， 以 甲醇 、 异戊醇 为溶剂， 反应 21.0h， 生成 3-氨基-4-苯基氨基苯甲酸
  参考文献：
  名称：

  Structure−Activity Relationships for 1-Phenylbenzimidazoles as Selective ATP Site Inhibitors of the Platelet-Derived Growth Factor Receptor

  摘要：

  1-Phenylbenzimidazoles are shown to be a new class of ATP-site inhibitors of the platelet-derived growth factor receptor (PDGFR). Structure-activity relationships (SARs) are narrow, with closely related heterocycles being inactive. A systematic study of substituted 1-phenyl-benzimidazoles showed clear SARs. Substituents at the 4'- and 3'-positions of the phenyl ring are tolerated but do not significantly improve activity, while substituents at the 2'-position abolish it. Substituents in the 2-, 4-, and 7-positions of the benzimidazole ring (with the exception of 4-OH) also abolish activity. Most substituents at the 5- and B-positions maintain or increase activity, with the 5-OH, 5-OMe, 5-COMe, and 5-CO2Me analogues being >10-fold more potent than the parent 1-phenylbenzimidazole. The 5-OMe analogue was both the most potent inhibitor, and showed the highest selectivity (50-fold) between PDGFR and FGFR isolated enzymes, and also a moderately effective inhibitor (IC50 = 1.9 mu M) of PDGF-stimulated PDGFR autophosphorylation in rat aorta smooth muscle cells.

  DOI：

  10.1021/jm9804681

文献信息

• Novel benzimidazole anti-inflammatory compounds
  申请人：Pfizer Inc.

  公开号：US20030092749A1

  公开（公告）日：2003-05-15

  The present invention relates to novel triazolo-pyridines of the formula I 1 wherein Het is an optionally substituted 5 -membered heterocycle containing one to two heteroatoms selected from nitrogen, sulfur and oxygen wherein at least one of said heteroatoms atoms must be nitrogen; R 2 is selected from the group consisting of hydrogen, (C 1 -C 6 )alkyl or other suitable substituents; R 3 is selected from the group consisting of hydrogen, (C 1 -C6)alkyl or other suitable substituents; s is an integer from 0-5; to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, repurfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

  本发明涉及公式I的新型三唑基吡啶 其中Het是一个可选择取代的 含有一个到两个氮、硫和氧杂原子的5元杂环，其中至少一个杂原子必须是氮; R 2 选自由氢、(C 1 -C 6 )烷基或其他适当的取代基组成的群; R 3 选自由氢、(C 1 -C6)烷基或其他适当的取代基组成的群; s是0-5之间的整数; 用于它们的制备的中间体，含有它们的药物组合物以及它们的药用。本发明的化合物是MAP激酶，优选为p38激酶的有效抑制剂。它们在治疗炎症、骨关节炎、类风湿性关节炎、癌症、中风或心脏病发中的再灌注或缺血、自身免疫疾病和其他疾病中有用。
• [EN] N-SUBSTITUTED BENZIMIDAZOLYL C-KIT INHIBITORS<br/>[FR] INHIBITEURS D'UN ENSEMBLE DE BENZIMIDAZOLYLE C N SUBSTITUE
  申请人：OSI PHARM INC

  公开号：WO2005021531A1

  公开（公告）日：2005-03-10

  Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, are useful in the treatment of cancer.

  公式（I）代表的化合物或其药用可接受的盐或N-氧化物，在癌症治疗中是有用的。
• N-substituted benzimidazolyl c-Kit inhibitors and combinatorial benzimidazole library
  申请人：Crew Philip Andrew

  公开号：US20060116402A1

  公开（公告）日：2006-06-01

  Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, are useful in the treatment of tumors. Combinatorial libraries composed of compounds represented by Formula (I) or benzimidazole compounds represented by Formula (II): are useful in providing compounds to assay for such therapeutically useful compounds.

  式(I)表示的化合物：或其药学上可接受的盐或N-氧化物，在肿瘤治疗中具有用途。由式(I)表示的化合物或式(II)表示的苯并咪唑化合物组成的组合库：在提供用于筛选此类治疗上有用的化合物的化合物方面具有用途。
• Structural Modifications of Benzimidazoles via Multi-Step Synthesis and Their Impact on Sirtuin-Inhibitory Activity
  作者：Yeong Keng Yoon、Tan Soo Choon

  DOI：10.1002/ardp.201500337

  日期：2016.1

  Benzimidazole derivatives have been shown to possess sirtuin‐inhibitory activity. In the continuous search for potent sirtuin inhibitors, systematic changes on the terminal benzene ring were performed on previously identified benzimidazole‐based sirtuin inhibitors, to further investigate their structure–activity relationships. It was demonstrated that the sirtuin activities of these novel compounds

  苯并咪唑衍生物已被证明具有抑制沉默调节蛋白的活性。在不断寻找有效的sirtuin抑制剂的过程中，对先前鉴定的苯并咪唑类sirtuin抑制剂末端苯环进行了系统的改变，以进一步研究它们的构效关系。结果表明，这些新化合物的sirtuin活性遵循除卤代取代基外，间位取代化合物的效力明显弱于邻位和对位取代化合物的趋势。进行分子对接研究以使这些观察合理化。除此之外，还讨论了用于合成有趣化合物的方法。
• N-substituted benzimidazolyl c-Kit inhibitors
  申请人：Bolger Joshua

  公开号：US20060189629A1

  公开（公告）日：2006-08-24

  Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, are useful in the treatment of cancer.

  由公式（I）表示的化合物或其药学上可接受的盐或N-氧化物，在癌症治疗中是有用的。