2-[(2-甲氧基苯基)氨基]-苯甲酸 | 13278-32-5

• 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-[(2-甲氧基苯基)氨基]-苯甲酸
• 英文名称: 2'-methoxydiphenylamine-2-carboxylic acid
• 英文别名: 2-(2-methoxyphenylamino)benzoic acid；N-(2-methoxyphenyl)anthranilic acid；N-(o-methoxyphenyl)anthranilic acid；N-(2-methoxy-phenyl)-anthranilic acid；N-(2-Methoxy-phenyl)-anthranilsaeure；2-o-Anisidino-benzoesaeure；2-(2-methoxyanilino)benzoic acid
• CAS: 13278-32-5
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD00477470
• 分子量: 243.262
• InChiKey: FPIMZRVJKYCPAX-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  399.3±27.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

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：
  0.071
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  2-[(2-甲氧基苯基)氨基]-苯甲酸 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-(2-methoxyethoxymethyl)-4-methoxy-9-acridone
  参考文献：
  名称：

  吖啶基间苯二酚作为具有协调饱和度的稳健氢键二维网络的自互补构建块。在客体改变、客体去除和主体改性时保留晶体结构

  摘要：

  吖啶基间苯二酚主体 3（9-（3,5-二羟基-1-苯基）吖啶）形成加合物，如 3.（苯）、3.（氯仿）、3.0.5（甲苯）和 3.（苯甲酸异丁酯）。在吖啶环上具有额外 OH 基团的改性吖啶醇主体 4（9-（3,5-二羟基-1-苯基）-4-羟基吖啶）提供诸如 4.（苯）、4.（氯仿）、4.0 之类的加合物。 5(甲苯).0.5(水)、4.(甲醇).(水)和4.(乙酸乙酯)。在晶体中，主体 3 和 4 形成氢键 (OH...OH) 聚（间苯二酚）链，这些链通过链间 OH...N 氢键连接在一起，形成配位饱和的 (OH...OH.. .N) 由双氢键和反平行堆叠、自互补环状二聚体 3(2) 或 4(2) 组成的 2D 网络作为刚性结构单元，否则柔性 OH...OH 氢键由此被引入类似环烷的结构。事实证明，该网络在上述加合物中保存得非常好。客体分子在许多情况下是无序的，它们被结合在留下的空腔中。小极性客体与主体

  DOI：

  10.1021/ja026704l
• 作为产物：
  描述：

  N-(2-甲氧基苯基)邻氨基苯甲酸甲酯 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以53%的产率得到2-[(2-甲氧基苯基)氨基]-苯甲酸
  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

• Synthesis and Characterization of 1-carboxyphenothiazine Derivatives Bearing Nitrogen Mustard as Promising Class of Antitubercular Agents
  作者：V.B. Kataria、M.J. Solanki、A.R. Trivedi、V.H. Shah

  DOI：10.2174/15701808113109990022

  日期：2013.10.1

  A series of 1-carboxyphenothiazines bearing nitrogen mustard was synthesized, characterized, and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. The results showed that compounds 5h, 5i and 5j found most active with percentage inhibition of 96, 91, and 92, respectively, at minimum inhibitory concentration (MIC) of 6.25 μg/mL. The structures of synthesized compounds were elucidated by various spectroscopic tools like IR, 1H NMR, 13C NMR, mass and elemental analysis.

  一系列含有氮芥的1-羧基吩噻嗪化合物被合成、表征，并对其对结核分枝杆菌H37Rv的体外抗结核活性进行了评估。结果显示，化合物5h、5i和5j的活性最高，在最低抑制浓度（MIC）为6.25 μg/mL时，抑制率分别为96%、91%和92%。合成化合物的结构通过各种光谱工具如IR、1H NMR、13C NMR、质谱和元素分析得以阐明。
• Substituted aminobenzamides and their use as agents which inhibit
  申请人：Sterling Drug Inc.

  公开号：US04510139A1

  公开（公告）日：1985-04-09

  Novel 2-(hydroxyphenylamino)benzamides and oxidation products thereof, useful as inhibitors of lipoxygenase, are of the formulas ##STR1## wherein R is hydrogen, lower-alkyl, halo or lower-alkoxy; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and N.dbd.Z is amino or substituted amino. The compounds of Formula I are prepared by de-etherification of the corresponding alkyl or benzyl ethers; and the compounds of Formula II are prepared by oxidation of the compounds of Formula I where R' is hydrogen and OH is in the 4-position.

  Novel 2-(羟基苯胺基)苯甲酰胺及其氧化产物，可用作芦丁氧化酶抑制剂，其化学式如下：##STR1## 其中R为氢、较低烷基、卤素或较低烷氧基；R'为氢或较低烷基；R"为氢、较低烷基或卤素；N.dbd.Z为氨基或取代氨基。式I的化合物通过相应的烷基或苄基醚的脱醚制备；式II的化合物通过氧化式I的化合物制备，其中R'为氢且OH位于4位。
• Substituted aminobenzoates, their preparation and use
  申请人：Sterling Drug Inc.

  公开号：US04515980A1

  公开（公告）日：1985-05-07

  Novel lower-alkyl 2-(hydroxyphenylamino)benzoates, useful as inhibitors of lipoxygenase, are of the formula ##STR1## wherein R is hydrogen, lower-alkyl or lower-alkoxy; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and Alk is lower-alkyl. The compounds are prepared by de-etherification of the corresponding alkyl or benzyl ethers.

  新型的下烷基2-(羟基苯胺基)苯甲酸酯，作为脂氧合酶抑制剂，其化学式为##STR1##其中R为氢、下烷基或下烷氧基；R'为氢或下烷基；R"为氢、下烷基或卤素；Alk为下烷基。这些化合物是通过相应的烷基或苄基醚的脱醚反应制备的。
• Synthesis of Novel Carbohydrate Acridinone Derivatives with Potential Biological Activities using 1,3‐Dipolar Cycloaddition
  作者：Mirta L. Fascio、Norma Beatriz D'Accorso、Rolando F. Pellón、Maite L. Docampo

  DOI：10.1080/00397910701575178

  日期：2007.12

  Abstract Novel 10‐[3‐(6‐hydroxy‐2,2‐dimethyltetrahydrofuro[2,3‐d][1,3]dioxol‐5‐yl)‐4,5‐dihydro‐5‐isoxazolyl]methyl}‐9(10H)‐acridinone derivatives (13–16) were synthesized by 1,3‐dipolar cycloaddition using the carbohydrate derivative as dipole and different 10‐allyl‐9(10H)‐acridinone derivatives (9–12) as dipolarophiles. The new cycloadducts as well as the dipolarophiles precursors were characterized

  摘要 10-[3-(6-hydroxy-2,2-二甲基四氢呋喃[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-5-isoxazolyl]methyl}- 9(10H)-吖啶酮衍生物 (13-16) 是通过 1,3-偶极环加成反应合成的，使用碳水化合物衍生物作为偶极子，不同的 10-烯丙基-9(10H)-吖啶酮衍生物 (9-12) 作为亲偶极体。新的环加合物以及亲偶极体前体通过光谱进行了表征。
• Synthesis and Computational Studies on Optoelectronically Important Novel Acridin-Isoindoline-1,3-Dione Derivatives
  作者：Smita Mane、Kariyappa Katagi、Raveendra Melavanki

  DOI：10.1007/s10895-019-02376-2

  日期：2019.5

  donor groups containing derivatives exhibited excellent properties as fluorescent compounds. Computational studies were done using DFT (Density Functional Theory) G09 software (B3LYP/6-311G++V(d,p)) basis sets in order to calculate the optical band gap and FMO (Frontier Molecular Orbital) energies. The chemical stability of the four derivatives was determined by means of chemical hardness (η) using HOMO-LUMO

  设计并合成了一系列新颖的2-（4-（4-（acridin-9-ylamino）phenyl）isoindoline-1,3-dione衍生物，即2-（4-（4-甲氧基acridin-9-ylamino）phenyl）isoindoline-1 ，3-二酮[S1]，2-（4-（3-氯rid啶-9基氨基）苯基）异吲哚啉-1,3-二酮[S2]，2-（4-（2-氟丙烯酸酯-9基氨基）苯基）异吲哚啉- 1,3-二酮[S3]，2-（4-（1,4-二氯ac啶-9基氨基）苯基）异吲哚啉-1,3-二酮[S4]。这些化合物的光物理，热性质通过光谱和热成像方法表征。记录了这些衍生物在不同溶剂中的吸光度和荧光光谱，以了解溶质和溶剂相互作用的作用。这些化合物显示出高的热稳定性，在250–287°C的范围内，热分解温度在失重5％的情况下。与这些化合物相比，含衍生物的供体基团表现出优异的荧光化合物性能。使用DFT（密度泛函理论）G09软件（B3LYP