2-(3,5-dimethylanilino)benzoic acid | 55602-36-3

• 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-(3,5-dimethylanilino)benzoic acid
• 英文别名: 3,5-Xylyl anthranilic acid
• CAS: 55602-36-3
• 化学式: C₁₅H₁₅NO₂
• mdl: MFCD19497396
• 分子量: 241.29
• InChiKey: LQAICXZTMFLLTO-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C
• 沸点：
  398.5±30.0 °C(Predicted)
• 密度：
  1.203±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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethylanilino)benzoic acid 在 锌 作用下， 生成 3,5-二甲基三苯胺
  参考文献：
  名称：

  Fries; Boeker; Wallbaum, Justus Liebigs Annalen der Chemie, 1934, vol. 509, p. 73,100

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3,5-bis-(methyl)phenyl)anthranilic acid methyl ester 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以52%的产率得到2-(3,5-dimethylanilino)benzoic 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

• Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety
  作者：Qidong Tang、Xin Zhai、Yayi Tu、Ping Wang、Linxiao Wang、Chunjiang Wu、Wenhui Wang、Hongbo Xie、Ping Gong、Pengwu Zheng

  DOI：10.1016/j.bmcl.2016.02.037

  日期：2016.4

  A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety were synthesized, and evaluated for their antiproliferative activity against 5 cancer cell lines (H460, HT-29, MKN-45, A549, and U87MG). Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 42 (c-Met/Flt-3 IC50 = 1.21/2

  合成了一系列带有2-oxo-4-chloro-1,2，dihydroquinoline-3-carboxamide部分的6,7-di取代-4-phenoxyquinoline衍生物，并评估了它们对5种癌细胞系（H460， HT-29，MKN-45，A549和U87MG）。大多数化合物显示出中等至出色的效力，并且与foretinib相比，最有前途的类似物42（c-Met / Flt-3 IC 50  = 1.21 / 2.15 nM）在体外对H460细胞系的活性提高了6.1倍。在体外评估了化合物42的酶促测定（c-Met，VEGFR-2，Flt-3，PDGFR-β，c-Kit和EGFR）。对接分析表明，化合物42可以与c-Met形成三个氢键 结构与活性之间的关系研究表明，在苯环的4位上，水溶性更强的环状叔胺和吸电子基团有助于抗肿瘤活性。
• Hydrogen-bonded dimer stacking induced emission of aminobenzoic acid compounds
  作者：Tianlei Zhou、Feng Li、Yan Fan、Weifeng Song、Xiaoyue Mu、Hongyu Zhang、Yue Wang

  DOI：10.1039/b900476a

  日期：——

  A series of aminobenzoic acid crystals with stacking-induced emission properties has been achieved and the packing structures of the hydrogen-bonded acid dimers provided an explanation for the emission characteristics of the crystals.

  我们获得了一系列具有堆叠诱导发射特性的氨基苯甲酸晶体，氢键酸二聚体的堆积结构为晶体的发射特性提供了解释。
• Preparation and Evaluation of Sterically Hindered Acridine Photocatalysts
  作者：Kirill A. Zhilyaev、Dmitry L. Lipilin、Mikhail D. Kosobokov、Aida I. Samigullina、Alexander D. Dilman

  DOI：10.1002/adsc.202200515

  日期：2022.9.20

  A practical nickel-catalyzed protocol for the synthesis of sterically hindered 9-arylacridines via Negishi type cross-coupling was developed. The method enables a convenient approach to a set of active acridine photocatalysts starting from commercially available 9-chloroacridine, inexpensive catalyst [NiCl2(Ph3P)2], and organozinc reagent with no need for additional ligands and precious metals. The

  开发了一种通过 Negishi 型交叉偶联合成空间位阻 9-芳基吖啶的实用镍催化方案。该方法可以方便地从市售的 9-氯吖啶、廉价催化剂 [NiCl 2 (Ph 3 P) 2 ] 和有机锌试剂开始制备一组活性吖啶光催化剂，而无需额外的配体和贵金属。合成协议可以很容易地以克级执行。在脱羧硫醇化和胺化反应中测试了所得吖啶的光催化效率。通过 X 射线分析研究了 19 种吖啶的结构，从而提出了与催化活性相关的空间描述符。
• Utilization of Aryl(TMP)iodonium Salts for Copper-Catalyzed <i>N</i>-Arylation of Isatoic Anhydrides: An Avenue to Fenamic Acid Derivatives and <i>N,N</i>′-Diarylindazol-3-ones
  作者：Raktim Abha Saikia、Khanindra Talukdar、Debabrat Pathak、Bipul Sarma、Ashim Jyoti Thakur

  DOI：10.1021/acs.joc.2c02762

  日期：2023.3.17

  isatoic anhydrides with unsymmetrical iodonium salts at room temperature. The developed catalytic protocol is mild and operationally simple, and aryl(TMP)iodonium trifluoroacetate is employed as the arylating partner. The methodology offers the broad applicability of both structurally and electronically diverse aryl groups from aryl(TMP)iodonium salts to access N-arylated isatoic anhydrides in moderate

  在此，我们报告了一种在室温下用不对称碘盐对铜催化的靛红酸酐进行N-芳基化的通用方法。开发的催化方案温和且操作简单，芳基（TMP）三氟乙酸碘用作芳基化伙伴。该方法提供了从芳基 (TMP) 碘盐中结构和电子不同的芳基基团的广泛适用性，以中等至优异的产率 (53–92%)获得N-芳基化靛红酸酐。此外，取代的靛红酸酐也同样符合该协议。为了证明N -arylation 过程的合成效用，我们还报告了一种生物相关的灭酸衍生物的替代方法和N , N' -diarylindazol-3-ones 在一锅法经济体系中。此外，还说明了氟灭酸的放大合成。
• Kaltenbronn; Scherrer; Short, Arzneimittel-Forschung/Drug Research, 1983, vol. 33, # 4 A, p. 621 - 627
  作者：Kaltenbronn、Scherrer、Short、Jones、Beatty、Saka、Winder、Wax、Williamson

  DOI：——

  日期：——