2-<(4-Methylphenyl)amino>benzoesaeure-methylester | 23868-15-7

• 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: 2-<(4-Methylphenyl)amino>benzoesaeure-methylester
• 英文别名: methyl 2‐[(4‐methylphenyl)amino]benzoate；N-(4-methylphenyl)anthranilic acid methyl ester；2-(4-methyl-anilino)-benzoic acid methyl ester；N-p-tolyl-anthranilic acid methyl ester；N-p-Tolyl-anthranilsaeure-methylester；2-(p-Tolylamino)-benzoesaeure-methylester；Methyl 2-(p-tolylamino)benzoate；methyl 2-(4-methylanilino)benzoate
• CAS: 23868-15-7
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: ZOMPXSOAWQYBGP-UHFFFAOYSA-N

物化性质

• 熔点：
  48.5 °C
• 沸点：
  374.0±25.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(4-Methylphenyl)amino>benzoesaeure-methylester 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以70%的产率得到2-[(4-甲基苯基)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
• 作为产物：
  描述：

  2-(三氟甲基磺酰氧基)苯甲酸甲酯 、 乙烷,三氯氟- 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 以99%的产率得到2-<(4-Methylphenyl)amino>benzoesaeure-methylester
  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

• Sodium Butylated Hydroxytoluene: A Functional Group Tolerant, Eco‐Friendly Base for Solvent‐Free, Pd‐Catalysed Amination
  作者：Volodymyr Semeniuchenko、Wilfried M. Braje、Michael G. Organ

  DOI：10.1002/chem.202101617

  日期：2021.9

  NaBHT (sodium 2,6-di-tert-butyl-4-methylphenolate), a strong, but hindered and lipophilic base, has been effectively paired with similarly lipophilic, high-reactivity Pd-NHC (N-heterocyclic carbene) catalysts to produce an ideal combination for performing solvent-free (melt) cross-coupling amination. The mild nucleophilicity of NaBHT, coupled with the anti-oxidant properties of its conjugate acid byproduct

  NaBHT（2,6-二叔丁基-4-甲基苯酚钠）是一种强但受阻且亲脂的碱，已与类似的亲脂性、高反应性 Pd-NHC（N-杂环卡宾）催化剂有效配对以生产进行无溶剂（熔融）交叉偶联胺化的理想组合。NaBHT 温和的亲核性，加上其共轭酸副产物的抗氧化特性，BHT 意味着该过程似乎没有官能团不相容性。在所有情况下，仅使用 0.1-0.2 mol% 的催化剂就观察到碱敏感和氧化还原活性官能团的高效偶联。使用该反应的标准碱 KOtBu 进行比较，导致大多数应用中偶联不良或完全降解 - 只有 NaBHT 有效。
• Polymerized thermally activated delayed fluorescence small molecules: long‐axis polymerization leads to a nearly concentration‐independent luminescence
  作者：Junqiao Ding、Xue Li、Libing Yan、Shen Liu、Shumeng Wang、Jiancheng Rao、Lei Zhao、Hongkun Tian、Lixiang Wang

  DOI：10.1002/anie.202300529

  日期：——

  A nearly concentration-independent luminescence has been demonstrated by polymerizing a donor-acceptor-donor type TADF small molecule through its long-axis direction rather than the short-axis one. The corresponding PLQY remains almost unchanged, leading a promising EQE up to 20 % in a whole doping control window of 5–100 wt. %.

  通过其长轴方向而不是短轴方向聚合供体-受体-供体型 TADF 小分子，证明了几乎与浓度无关的发光。相应的 PLQY 几乎保持不变，在 5-100 wt 的整个掺杂控制窗口中导致有希望的 EQE 高达 20%。%。
• Legrand,L.; Lozac'h,N., Bulletin de la Societe Chimique de France, 1969, p. 1173 - 1182
  作者：Legrand,L.、Lozac'h,N.

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• Synthèses dans la classe des carbazines VII
  作者：Henri Goldstein、Gérald Huser

  DOI：10.1002/hlca.19440270176

  日期：——
• Hellwinkel, Dieter; Ittemann, Peter, Chemische Berichte, 1986, vol. 119, # 10, p. 3165 - 3197
  作者：Hellwinkel, Dieter、Ittemann, Peter

  DOI：——

  日期：——