5-甲基-2-(对甲苯氨基)苯甲酸 | 24173-43-1

• 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: 5-甲基-2-(对甲苯氨基)苯甲酸
• 英文名称: 5-methyl-2-(p-tolylamino)benzoic acid
• 英文别名: 5-methyl-N-(4'-methyl)phenylanthranilic acid；2-(N-(4-methylphenyl)amino)-5-methylbenzoic acid；5-methyl-2-p-toluidino-benzoic acid；5-Methyl-2-p-toluidino-benzoesaeure；N-(p-Tolyl)-5-methylanthranilic acid；5-methyl-2-(4-methylanilino)benzoic acid
• CAS: 24173-43-1
• 化学式: C₁₅H₁₅NO₂
• mdl: MFCD19497412
• 分子量: 241.29
• InChiKey: JRRSLUSVHFALSP-UHFFFAOYSA-N

物化性质

• 沸点：
  415.4±33.0 °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：

  5-甲基-2-(对甲苯氨基)苯甲酸 在 硫酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 9-chloro-2,7-dimethylacridine
  参考文献：
  名称：

  Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression

  摘要：

  The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.

  DOI：

  10.1021/acs.jmedchem.9b01917
• 作为产物：
  描述：

  5-methyl-1-(p-tolyl)indoline-2,3-dione 在 水 、 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 反应 4.0h， 以97%的产率得到5-甲基-2-(对甲苯氨基)苯甲酸
  参考文献：
  名称：

  吲哚与硝基烯烃不对称弗瑞德-克拉夫茨烷基化反应中柔性配体骨架优先的直接实验证据

  摘要：

  摘要：通过柔性配体/ZnCl 2 配合物的XRD分析以及平面刚性支架合成二氢吖啶连接的双(恶唑啉)配体，获得了柔性配体骨架在不对称Friedel-Crafts烷基化中优先的直接实验证据。一个没有 NH 的过渡态模型……？提出了刚性配体的相互作用来解释绝对构型的反转。关键词：刚性支架，柔性支架，二苯胺，二氢吖啶，双（恶唑啉），Friedel-Crafts 烷基化。引言 自从关于恶唑啉 [1] 的开创性报道以来，化学家在配位化学、合成化学和催化领域广泛开发了手性双（恶唑啉）配体 [2]。已经从市售的氨基醇和羧酸/醛通过简便的程序合成了大量具有不同支架的配体，这说明了它们在应用中的巨大潜力。一些配体支架从大量报道中脱颖而出，并在不同的不对称转化中获得广泛应用 [3]，而大多数配体支架仅在特定情况下才给出令人满意的结果。这种情况使得为指定反应设计新型配体成为一项困难且无利可图的工作。近年来，一些小

  DOI：

  10.2174/157017810790796354

文献信息

• Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters
  作者：Weiyu Li、Hao Xu、Lei Zhou

  DOI：10.1039/d1ob00691f

  日期：——

  oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.

  描述了吖啶类和甲硅烷基重氮烯醇化物的 MsOH 催化的氧化交叉偶联和所得重氮产物的 Rh 2 (OAc) 4催化的重排。该反应以良好的收率提供了各种 γ-(9-acridanylidene)-β-酮酯，它们带有一个活性 α-亚甲基单元用于进一步的官能化。
• The Effects of Substituents Introduced into 9-Aminoacridine on Frameshift Mutagenicity and DNA Binding Affinity
  作者：Hideyuki Tomosaka、Saburo Omata、Eietsu Hasegawa、Kentaro Anzai

  DOI：10.1271/bbb.61.1121

  日期：1997.1

  Some derivatives of 9-aminoacridine (1) were synthesized, and their frameshift mutagenicity and DNA binding affinity were studied. The introduction of a methyl group into the acridine ring of 1 reduced the mutagenic activity and the intercalative DNA binding affinity, while the introduction of chlorine increased them. Halogenated derivatives of 1 showed higher toxicity against Salmonella typhimurium TA1537.

  合成了一些9-氨基吖啶（1）的衍生物，并研究了它们的框移突变性和DNA结合亲和力。向1的吖啶环中引入甲基基团降低了突变活性和插入性DNA结合亲和力，而引入氯原子则增强了它们。1的卤代衍生物对沙门氏菌typhimurium TA1537显示出更高的毒性。
• Simultaneous production of p-tolualdehyde and hydrogen peroxide in photocatalytic oxygenation of p-xylene and reduction of oxygen with 9-mesityl-10-methylacridinium ion derivatives
  作者：Kei Ohkubo、Kentaro Mizushima、Ryosuke Iwata、Kazunori Souma、Nobuo Suzuki、Shunichi Fukuzumi

  DOI：10.1039/b920606j

  日期：——

  Photooxygenation of p-xylene by oxygen occurs efficiently under photoirradiation of 9-mesityl-2,7,10-trimethylacridinium ion (Me2Acr+–Mes) to yield p-tolualdehyde and hydrogen peroxide, which is initiated via photoinduced electron transfer of Me2Acr+–Mes to produce the electron-transfer state.

  在 9-甲巯基-2,7,10-三甲基吖啶离子（Me2Acr+-Mes）的光照射下，对二甲苯在氧气的作用下发生光氧化反应，生成对甲苯酚和过氧化氢，这种反应是通过 Me2Acr+-Mes 的光诱导电子转移产生电子转移态开始的。
• PhI(OAc)₂-Mediated Intramolecular Oxidative Aryl-Aldehyde C<i>sp</i>²–C<i>sp</i>² Bond Formation: Metal-Free Synthesis of Acridone Derivatives
  作者：Zisheng Zheng、Longyang Dian、Yucheng Yuan、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/jo5011697

  日期：2014.8.15

  A metal-free protocol for direct aryl-aldehyde Csp(2)-Csp(2) bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.
• Preparation and Characterization of Thermochemiluminescent Acridine-Containing 1,2-Dioxetanes as Promising Ultrasensitive Labels in Bioanalysis
  作者：Massimo Di Fusco、Arianna Quintavalla、Claudio Trombini、Marco Lombardo、Aldo Roda、Massimo Guardigli、Mara Mirasoli

  DOI：10.1021/jo401683r

  日期：2013.11.15

  Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 degrees C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.