methyl 2-<(3-carbomethoxyphenyl)amino>benzoate | 114918-37-5

• 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: methyl 2-<(3-carbomethoxyphenyl)amino>benzoate
• 英文别名: N-(3-(methoxycarbonyl)phenyl)anthranilic acid methyl ester；methyl 2-(3-carbomethoxyphenylamino)-benzoate；methyl 2-(3-methoxycarbonylanilino)benzoate
• CAS: 114918-37-5
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: YFPYIONRNZYEKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  418.9±30.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-<(3-carbomethoxyphenyl)amino>benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2,3-亚氨基二苯甲酸
  参考文献：
  名称：

  基于邻氨基苯甲酸的运甲状腺素蛋白淀粉样蛋白原纤维抑制剂的合成和评价。

  摘要：

  合成八个小分子以评估N-取代邻氨基苯甲酸的结构活性关系（SAR）。通过邻氨基苯甲酸甲酯的苄基化或芳基化合成分子。基于光散射的淀粉样蛋白原纤维形成试验用于评估体外转甲状腺素蛋白（TTR）淀粉样蛋白原纤维形成的潜在抑制剂。间羧基苯基化和邻三氟甲基苯基化的邻氨基苯甲酸是有效的抑制剂，将经受进一步的SAR和结构分析。

  DOI：

  10.1016/s0960-894x(98)00696-9
• 作为产物：
  描述：

  间氨基苯甲酸 在 盐酸 、 铜 、 potassium carbonate 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 methyl 2-<(3-carbomethoxyphenyl)amino>benzoate
  参考文献：
  名称：

  Structure-activity relationship of quinazolinedione inhibitors of calcium-independent phosphodiesterase

  摘要：

  A series of quinazolinediones and azaquinazolinediones is described which possess potent inhibitory activity toward the calcium-independent phosphodiesterase enzyme (CaIPDE). In vivo testing showed that this in vitro activity translates to animal models predictive of chronic diseases such as depression and inflammation. These results support the hypothesis that inhibition of CaIPDE may lead to useful activity in such chronic diseases.

  DOI：

  10.1021/jm00106a024

文献信息

• Development of Potent and Selective Inhibitors of Aldo–Keto Reductase 1C3 (Type 5 17β-Hydroxysteroid Dehydrogenase) Based on <i>N</i>-Phenyl-Aminobenzoates and Their Structure–Activity Relationships
  作者：Adegoke O. Adeniji、Barry M. Twenter、Michael C. Byrns、Yi Jin、Mo Chen、Jeffrey D. Winkler、Trevor M. Penning

  DOI：10.1021/jm201547v

  日期：2012.3.8

  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.
• Quinazolinediones and pyridopyrimidinediones
  申请人：PFIZER INC.

  公开号：EP0260817B1

  公开（公告）日：1991-05-15
• LOWE, J. A.
  作者：LOWE, J. A.

  DOI：——

  日期：——
• LOWE, JOHN A.
  作者：LOWE, JOHN A.

  DOI：——

  日期：——
• LOWE, JOHN A. (III);ARCHER, ROBERT L.;CHAPIN, DOUGLAS S.;CHENG, JOHN B.;H+, J. MED. CHEM., 34,(1991) N, C. 624-628
  作者：LOWE, JOHN A. (III)、ARCHER, ROBERT L.、CHAPIN, DOUGLAS S.、CHENG, JOHN B.、H+

  DOI：——

  日期：——