4'-Methyl-4-carboxy-diphenylamin | 100866-44-2

• 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: 4'-Methyl-4-carboxy-diphenylamin
• 英文别名: 4-[(4-methylphenyl)amino]benzoic acid；4-p-toluidino-benzoic acid；4-p-Toluidino-benzoesaeure；4-(4-methylanilino)benzoic acid
• CAS: 100866-44-2
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: VICFCQQQOPXTJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-P-苯甲基氨基苯甲酸甲酯 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以88%的产率得到4'-Methyl-4-carboxy-diphenylamin
  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

• Solvatomorphism and first-time observation of acid–acid catemer in 4-phenylamino-benzoic acids
  作者：Xiaoting Liu、Jingliang Cui、Qun Zeng、Liwen Fang、Peng-Yu Liang、Pan-Pan Zhou、Sean Parkin、Tonglei Li、Shigang Ruan、Sihui Long

  DOI：10.1039/d3ra04102f

  日期：——

  other solvate, for compounds 1, 3 and 8, and one form for the other compounds. The crystal structures were determined by single-crystal XRD. All the 4-PABAs in the crystal structures are highly twisted, and all the solvent-free crystals are based on the conventional acid-acid dimer motif, except for 2, which has a rarely observed acid-acid catemer motif. Two of the solvates (1-S and 8-S) have pyridine in

  为了研究 4-苯氨基苯甲酸 (4-PABA) 的多态性，特别是取代对这些化合物多态性的影响，研究了一系列取代位置不同的 4-PABA (1-8)合成了其多态性，并首次研究了它们的多态行为。相对全面的多晶型物筛选发现了化合物 1、3 和 8 的两种形式，一种是无溶剂形式，另一种是溶剂化物形式，以及一种其他化合物形式。通过单晶 XRD 确定晶体结构。晶体结构中的所有4-PABA都是高度扭曲的，并且所有无溶剂晶体都基于传统的酸-酸二聚体基序，除了2，它具有很少观察到的酸-酸二聚体基序。其中两种溶剂化物（1-S 和 8-S）在晶格中含有吡啶，而另一种（3-S）则含有二氯甲烷。观察结果表明，构象灵活性或取代单独或两者的组合都不会导致这些化合物的多态性，这与芬那酸的多态性形成鲜明对比。通过差示扫描量热法研究了每个体系的热性质，并通过热重分析研究了溶剂化物的去溶剂化。通过赫什菲尔德表面分析和分子动力学模
• Photosensitive composition and negative working lithographic printing plate
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP1249731A2

  公开（公告）日：2002-10-16

  A photosensitive composition comprising a resin containing a repeating unit corresponding to a monomer having a structure represented by formula (I) defined in the specification, and a negative working lithographic printing plate having a negative working photosensitive layer comprising the above-described photosensitive composition.

  一种感光组合物，包含一种树脂，该树脂含有与单体相对应的重复单元，该单体的结构由说明书中定义的式 (I) 表示；以及一种底片工作平版印刷板，该底片工作感光层包含上述感光组合物。
• Light sensitive planographic printing plate material
  申请人：Matsumura Toshiyuki

  公开号：US20050181301A1

  公开（公告）日：2005-08-18

  Disclosed is a light sensitive planographic printing plate material comprising a hydrophilic support and provided thereon, a light sensitve layer containing (A) an infrared absorbing dye, (B) a radical generating agent, and (C) a radically polymerizable compound, the light sensitve layer being an outermost layer, wherein the radical generating agent is selected from the group consisting of a sulfonium salt, a iodonium salt and a diazonium salt, and the radically polymerizable compound is a radically polymerizable oxirane compound having an oxirane ring in the molecule.

  本发明公开了一种光敏平版印刷板材料，该材料包括亲水性支撑物，其上有光敏层，该光敏层含有（A）红外吸收染料，（B）自由基生成剂，和（C）可辐射聚合的化合物，光敏层为最外层，其中自由基生成剂选自由锍盐、碘盐和重氮盐组成的组，而可辐射聚合的化合物选自由锍盐、碘盐和重氮盐组成的组、光敏层为最外层，其中自由基发生剂选自由锍盐、碘盐和重氮盐组成的组，可辐射聚合化合物为分子中含有环氧乙烷环的可辐射聚合环氧乙烷化合物。
• Kisber; Putschkow, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2208,2210; engl. Ausg. S. 2267, 2268
  作者：Kisber、Putschkow

  DOI：——

  日期：——
• US6858373B2
  申请人：——

  公开号：US6858373B2

  公开（公告）日：2005-02-22