methyl 4-(3-methoxyphenylamino)benzoate

• 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 4-(3-methoxyphenylamino)benzoate
• 英文别名: 4-[(3-methoxyphenyl)amino]benzoic acid methyl ester；methyl 4-(3-methoxyanilino)benzoate
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: WPXDDCPYINVEBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(3-methoxyphenylamino)benzoate 在 氧气 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 生成 clausine C
  参考文献：
  名称：

  One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling

  摘要：

  一种常见的钯催化剂可以在适当的添加剂存在下促进“一锅法”N-芳基化和氧化偶联：在标准条件下钯催化苯胺与芳基三氟甲磺酸酯的N-芳基化，随后在氧气或空气氛围中添加醋酸，可以获得各类功能化的卡巴唑，产率良好至优异。

  DOI：

  10.1039/b707899d
• 作为产物：
  描述：

  对溴苯甲酸甲酯 、 间氨基苯甲醚 在 palladium diacetate 、 potassium carbonate 、 S-1,1'-联-2-萘酚 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到methyl 4-(3-methoxyphenylamino)benzoate
  参考文献：
  名称：

  掌握三环系统以获得所需的功能性大麻素活性

  摘要：

  人们对使用大麻素受体 2 (CB2) 激动剂治疗神经性疼痛和其他适应症越来越感兴趣。为了继续我们正在进行的旨在开发新的小分子大麻素配体的计划，我们合成了一系列新型咔唑和 γ-咔啉衍生物。新合成的化合物的亲和力通过对人 CB2 大麻素受体和大鼠 CB1 大麻素受体的竞争性放射性配体置换试验确定。使用受体内化和 [ 35 S] GTP-γ-S 测定法表征对人 CB1 和 CB2 受体的功能活性和选择性。咔唑系列的构效关系和优化研究导致发现了非选择性 CB1 和 CB2 激动剂，化合物4. 我们随后为提高该先导化合物的 CB2 选择性所做的研究工作导致了 CB2 选择性化合物64的发现，该化合物可强力内化 CB2 受体。在神经性疼痛的大鼠模型中，化合物64对疼痛超敏反应具有强效抑制作用。还发现了其他有效的 CB2 受体选择性化合物，包括化合物63和68，以及选择性 CB1 激动剂，化合物74。此外，我们还鉴定了

  DOI：

  10.1016/j.ejmech.2013.09.038

文献信息

• Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines
  作者：Xinyu Guan、Haoran Zhu、Tom G. Driver

  DOI：10.1021/acscatal.1c03113

  日期：2021.10.15

  copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic

  描述了使用苯基硅烷作为化学计量末端还原剂的硝基芳烃与芳基硼酸形成二芳基胺的简单铜催化反应的开发和研究。这种交叉偶联反应只需要 2 mol% 的 CuX 和 4 mol% 的二膦即可成功，并且可以容忍硝基芳烃或芳基硼酸上的多种官能团，从而以良好的收率提供胺。机理研究表明，交叉偶联反应通过亚硝基芳烃中间体进行，并且铜需要催化硝基芳烃的脱氧以提供亚硝基芳烃和亚硝基芳烃与芳基硼酸的 C-NAr 键形成。
• Novel Tricyclic Modulators of Cannabinoid Receptors
  申请人：Diaz Philippe

  公开号：US20120039804A1

  公开（公告）日：2012-02-16

  The compounds of the invention are modulators of cannabinoid receptors CB1 or CB2. The compounds can be used for the prevention or treatment of, e.g., pain, cancer, skin diseases, weight-associated disorders, chemical addictions, psychiatric disorders, neurodegenerative disorders, bone diseases, and inflammatory diseases. The compounds of the invention can further be used to study these diseases and disorders, as well as cannabinoid receptor biology, by coupling the compounds to, e.g., imaging agents.

  该发明的化合物是大麻素受体CB1或CB2的调节剂。这些化合物可用于预防或治疗疼痛、癌症、皮肤疾病、与体重相关的疾病、化学成瘾、精神障碍、神经退行性疾病、骨疾病和炎症性疾病等。该发明的化合物还可用于研究这些疾病和障碍，以及大麻素受体生物学，方法是将这些化合物与成像剂等耦合。
• One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
  作者：Toshiaki Watanabe、Satoshi Ueda、Shinsuke Inuki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1039/b707899d

  日期：——

  One-pot N-arylation and oxidative coupling can be promoted by a common palladium catalyst in the presence of appropriate additives: palladium-catalyzed N-arylation of anilines with aryl triflates under the standard conditions followed by addition of acetic acid under oxygen or air atmosphere afforded various types of functionalized carbazoles in good to excellent yields.

  一种常见的钯催化剂可以在适当的添加剂存在下促进“一锅法”N-芳基化和氧化偶联：在标准条件下钯催化苯胺与芳基三氟甲磺酸酯的N-芳基化，随后在氧气或空气氛围中添加醋酸，可以获得各类功能化的卡巴唑，产率良好至优异。
• Kinesin Spindle Protein (KSP) Inhibitors with 2,3-Fused Indole Scaffolds
  作者：Shinya Oishi、Toshiaki Watanabe、Jun-ichi Sawada、Akira Asai、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1021/jm100476d

  日期：2010.7.8

  On the basis of a common 2,3-fused indole substructure within the complex frameworks of terpendole E and other KSP inhibitors, the carbazoles with a bulky alkyl group were identified as a novel KSP inhibitory scaffold. Additionally, among several naturally occurring cell growth inhibitors with 2,3-fused indole structures, β-carboline alkaloids, harman and harmine, showed moderate inhibition of KSP

  有丝分裂驱动蛋白纺锤体蛋白（KSP）在细胞分裂过程中参与了双极纺锤体的组装。根据萜烯E和其他KSP抑制剂复杂框架中常见的2,3-稠合的吲哚亚结构，具有庞大烷基的咔唑被鉴定为新型KSP抑制支架。另外，在具有2，3-融合的吲哚结构的几种天然存在的细胞生长抑制剂中，β-咔啉生物碱，harman和harmine显示出对KSP的中等抑制作用。
• 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.