2-苯胺基-3-甲氧基-苯甲酸 | 59425-27-3

• 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: 2-苯胺基-3-甲氧基-苯甲酸
• 英文名称: 2-anilino-3-methoxy-benzoic acid
• 英文别名: 2-Anilino-3-methoxy-benzoesaeure；3-Methoxy-N-phenyl-anthranilsaeure；3-Methoxy-2-(phenylamino)benzoic acid；2-anilino-3-methoxybenzoic acid
• CAS: 59425-27-3
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: URWJWWULDLOJGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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

• 作为反应物：
  描述：

  2-苯胺基-3-甲氧基-苯甲酸 在 lithium aluminium tetrahydride 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 3-methoxy-2-(methyl(phenyl)amino)benzaldehyde
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h
• 作为产物：
  描述：

  2-碘-3-甲氧基苯甲酸 、 苯胺 在 copper diacetate 、 sodium acetate 作用下， 以 水 为溶剂， 生成 2-苯胺基-3-甲氧基-苯甲酸
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h

文献信息

• Evaluation of synthetic acridones and 4-quinolinones as potent inhibitors of cathepsins L and V
  作者：Emerson F. Marques、Mauro A. Bueno、Patrícia D. Duarte、Larissa R.S.P. Silva、Ariani M. Martinelli、Caio Y. dos Santos、Richele P. Severino、Dieter Brömme、Paulo C. Vieira、Arlene G. Corrêa

  DOI：10.1016/j.ejmech.2012.04.002

  日期：2012.8

  Cathepsins, also known as lysosomal cysteine peptidases, are members of the papain-like peptidase family, involved in different physiological processes. In addition, cathepsins are implicated in many pathological conditions. This report describes the synthesis and evaluation of a series of N-arylanthranilic acids, acridones, and 4-quinolinones as inhibitors of cathepsins V and L The kinetics revealed that compounds of the classes of acridones are reversible competitive inhibitors of the target enzyme with affinities in the low micromolar range. They represent promising lead candidates for the discovery of novel competitive cathepsin inhibitors with enhanced selectivity and potency. On the other hand, 4-quinolinones were noncompetitive inhibitors and N-arylanthranilic acids were uncompetitive inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Gleu; Nitzsche, Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 153, p. 200,213
  作者：Gleu、Nitzsche

  DOI：——

  日期：——
• Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth
  作者：Aleksandar Putic、Lambert Stecher、Helge Prinz、Klaus Müller

  DOI：10.1016/j.ejmech.2010.04.013

  日期：2010.8

  A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones. (C) 2010 Elsevier Masson SAS. All rights reserved.
• KIMURA, MICHIO;OKABAYASHI, ICHIZO;KATO, AKIRA, CHEM. AND PHARM. BULL., 37,(1989) N, C. 697-701
  作者：KIMURA, MICHIO、OKABAYASHI, ICHIZO、KATO, AKIRA

  DOI：——

  日期：——
• BURKARTSMAIER A.; MUTSCHLER E., ARCH. PHARM. <APBD-AJ>, 1976, 309, NO 3, 228-233
  作者：BURKARTSMAIER A.、 MUTSCHLER E.

  DOI：——

  日期：——