N-(4-acetylphenyl)anthranilic acid | 23600-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)anthranilic acid
• 英文别名: N-(4-acetylphenyl)anthanilic acid；N-(4-acetyl-phenyl)-anthranilic acid；N-(4-Acetyl-phenyl)-anthranilsaeure；(Acetyl-4-phenyl)-(carboxyl-2'-phenyl)-amin；4'-Acetyl-diphenylamin-2-carbonsaeure；2-[(4-Acetylphenyl)amino]benzoic acid；2-(4-acetylanilino)benzoic acid
• CAS: 23600-82-0
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: QYOXABROWSLTCG-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C(Solv: ethanol (64-17-5))
• 沸点：
  455.0±30.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)anthranilic acid 在 camphor-10-sulfonic acid 作用下， 生成 N-(4-acetyl-phenyl)-N-phenyl-acetamide
  参考文献：
  名称：

  二苯胺的一些衍生物

  摘要：

  DOI：

  10.1039/jr9550001278
• 作为产物：
  描述：

  methyl 2-(4'-acetylphenylamino)benzoate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以79%的产率得到N-(4-acetylphenyl)anthranilic acid
  参考文献：
  名称：

  Development of Potent and Selective Inhibitors of Aldo–Keto Reductase 1C3 (Type 5 17β-Hydroxysteroid Dehydrogenase) Based on N-Phenyl-Aminobenzoates and Their Structure–Activity Relationships

  摘要：

  Aldo-keto reductase 1C3 (AKR1C3; type 5 17 beta-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5 alpha-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of Sa-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.

  DOI：

  10.1021/jm201547v

文献信息

• Studies on 4(1H)-Quinazolinones. 5. Synthesis and Antiinflammatory Activity of 4(1H)-Quinazolinone Derivatives
  作者：Ken-ichi Ozaki、Yoshihisa Yamada、Toyonari Oine、Tōru Ishizuka、Yoshio Iwasawa

  DOI：10.1021/jm50001a006

  日期：1985.5

  new 4(1H)-quinazolinones were synthesized and evaluated in the carrageenin-induced paw edema test. Most of the compounds were obtained by the cyclization of the appropriately substituted anthranilamides with acid chlorides, followed by further chemical transformation. Structure-activity data suggest that 2-isopropyl-1-phenyl-, 2-cyclopropyl-1-phenyl-, and 1-isopropyl-2-phenyl-4(1H)-quinazolinones afford

  合成了许多新的4（1H）-喹唑啉酮，并在角叉菜胶诱导的爪水肿试验中进行了评估。大多数化合物是通过将适当取代的邻氨基苯甲酰胺与酰氯环合，然后进一步化学转化而获得的。结构活性数据表明2-异丙基-1-苯基-，2-环丙基-1-苯基-和1-异丙基-2-苯基-4（1H）-喹唑啉酮具有最佳效价，卤素原子的存在为首选活动。肾上腺切除术不影响抗炎测试结果。1-异丙基-（2-氟苯基）-4-（1H）-喹唑啉酮（50）显示出兼顾功效和副作用的最佳结果。
• Itier,J.; Casadevall,A., Bulletin de la Societe Chimique de France, 1969, p. 2342 - 2355
  作者：Itier,J.、Casadevall,A.

  DOI：——

  日期：——
• Montanari, Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 33,37,41
  作者：Montanari

  DOI：——

  日期：——
• Kauffman, Joel M.; Taraporewala, Irach B., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1557 - 1559
  作者：Kauffman, Joel M.、Taraporewala, Irach B.

  DOI：——

  日期：——
• KAUFFMAN, J. M.;TARAPOREWALA, I. B., J. HETEROCYCL. CHEM., 1982, 19, N 6, 1557-1559
  作者：KAUFFMAN, J. M.、TARAPOREWALA, I. B.

  DOI：——

  日期：——