(4'-氨基-4-联苯基)甲醇 | 393522-98-0

• 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: (4'-氨基-4-联苯基)甲醇
• 英文名称: 4-(4-hydroxybenzyl)aniline
• 英文别名: 4-amino-4'-hydroxymethylbiphenyl；4-(4-Aminophenyl)benzyl alcohol；[4-(4-aminophenyl)phenyl]methanol
• CAS: 393522-98-0
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: NHVWYPKGMWDYPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4'-氨基-4-联苯基)甲醇 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 4'-amino-(4-chloromethyl)biphenyl
  参考文献：
  名称：

  Design, Biological Evaluation, and Molecular Modeling of Tetrahydroisoquinoline Derivatives: Discovery of A Potent P-Glycoprotein Ligand Overcoming Multidrug Resistance in Cancer Stem Cells

  摘要：

  P-Glycoprotein is a well-known membrane transporter responsible for the efflux of an ample spectrum of anticancer drugs. Its relevance in the management of cancer chemotherapy is increased in view of its high expression in cancer stem cells, a population of cancer cells with strong tumor-promoting ability. In the present study, a series of compounds were synthesized through structure modulation of [4'-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-bipheny1-4-ol] (MC70), modifying the phenolic group of the lead compound. Among them, compound 513 emerged for its activity against the transporter (EC50 = 15 nM) and was capable of restoring doxorubicin antiproliferative activity at nontoxic concentration. Its behavior was rationalized through a molecular modeling study consisting of a well-tempered metadynamics simulation, which allowed one to identify the most favorable binding pose, and of a subsequent molecular dynamics run, which indicated a peculiar effect of the compound on the motion pattern of the transporter.

  DOI：

  10.1021/acs.jmedchem.8b01655
• 作为产物：
  描述：

  4-羟甲基苯硼酸 、 对碘苯胺 在 palladium diacetate 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以82%的产率得到(4'-氨基-4-联苯基)甲醇
  参考文献：
  名称：

  异醇大双环分子容器的一级酒精附加交叉偶氮苯的一步一步空气氧化转化。

  摘要：

  一系列的氧醚三氨基异位大环化合物（L1 – L4）合成了具有各种腔尺寸的）并探索了它们的Cu（II）催化伯醇基苯胺与几种芳族胺的选择性单步空中氧化交联，以形成伯醇附加的交叉偶氮苯（POCAB）。该转变的优点在于，由于该系列大双环容器的保护性氧醚口袋，在该氧化过程中易于氧化的苄基/伯醇基保持不受阻碍的状态。分子容器的各种尺寸已显示出对底物的特定大小的互补选择，以进行区域选择性POCAB产物的有效合成。为了确定基于三维腔体的添加剂的要求，已经在大自行车存在的情况下检查了特定的催化反应（L2和L3）与大环（MC1和MC2）以及三脚架无环（AC1和AC2）类似的组件。随后，L1 - L4被广泛用于多达44种POCAB的合成，并以不同的光谱技术和单晶X射线衍射研究为特征。

  DOI：

  10.1021/acs.joc.1c00409

文献信息

• BI-FUNCTIONAL QUINOLINE ANALOGS
  申请人：Baker William R.

  公开号：US20110275622A1

  公开（公告）日：2011-11-10

  Provided are compounds of Formula I: wherein X is: R 1 and R 2 together with the phenyl to which they are bound may form a bicyclic, fused heterocyclic ring, and all other variables are as defined herein, as well as their use in treating pulmonary inflammation or bronchoconstriction and compositions comprising and processes for preparing the same.

  提供的是以下化合物的结构式：其中X是：R1和R2，与它们结合的苯基一起可以形成一个螺环的、融合的杂环环，所有其他变量如本文所定义，以及它们在治疗肺部炎症或支气管痉挛中的应用，以及包含它们的组合物和制备这些化合物的方法。
• One molecule two goals: A selective P-glycoprotein modulator increases drug transport across gastro-intestinal barrier and recovers doxorubicin toxicity in multidrug resistant cancer cells
  作者：Marialessandra Contino、Stefano Guglielmo、Chiara Riganti、Giulia Antonello、Maria Grazia Perrone、Roberta Giampietro、Barbara Rolando、Roberta Fruttero、Nicola A. Colabufo

  DOI：10.1016/j.ejmech.2020.112843

  日期：2020.12

  cytotoxic activity of a well-known anti-cancer agent and P-gp substrate, doxorubicin, as first proof of concept. Moreover, compound 8b was also tested in an in vitro model of competent gastro-intestinal (GI) barrier (Caco-2 cells) for its ability to inhibit P-gp, present on luminal side, and increase the apical-to-basolateral transport of several structurally uncorrelated drugs, belonging to different therapeutic

  在本研究中，合成了一系列四氢异喹啉衍生物，并评估了它们对三种ABC转运蛋白P-gp，MRP1和BCRP的活性。该化合物被证明对P-gp具有选择性。其中之一8b表现出纳摩尔范围内的活性（EC 50 = 94 nM）。因此，测试化合物8b恢复众所周知的抗癌剂和P-gp底物阿霉素的细胞毒性活性的能力，这是概念的第一个证明。此外，化合物8b在感受态胃肠道（GI）屏障（Caco-2细胞）的体外模型中也测试了其抑制P-gp的能力，该能力存在于腔侧，并增加了几种结构不相关的顶突向基底外侧的转运药物，属于不同的治疗领域，但被P-gp主动排泄。值得注意的是，通过8b的浓度增加了药物通过GI屏障的转运，该浓度没有毒性，也没有对屏障功能的干扰作用。建立了体外模拟消化过程：有趣的是，在模拟消化过程之后也保留了8b对地高辛运输的影响。该结果可能表明8b作为一种安全和有效的P-gp的调制器，可以增加的施用的药物广谱的
• Methods for making colorant compounds
  申请人：Xerox Corporation.

  公开号：US20040082801A1

  公开（公告）日：2004-04-29

  Disclosed is a process for preparing a colorant of the formula 1 wherein Y is a hydrogen atom or a bromine atom, n is an integer of 0, 1, 2, 3, or 4, R 1 is an alkylene group or an arylalkylene group, R 2 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and R 4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, can be prepared by a process which comprises (a) preparing a first reaction mixture by admixing (1) leucoquinizarin and, optionally, quinizarin, (2) an aminobenzene substituted with an alcohol group of the formula —R 1 —OH, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula 2 followed by (b) converting the colorant thus prepared to either (i) an ester-substituted colorant by reaction with an esterification compound which is either (A) an anhydride of the formula 3 or (B) an acid of the formula R 2 COOH in the presence of an optional esterification catalyst, or (ii) a urethane-substituted colorant by reaction with an isocyanate compound of the formula R 4 —N═C═O and (c) brominating the colorant thus prepared, wherein either conversion to ester or urethane can be performed before bromination or bromination can be performed before conversion to ester or urethane.

  本发明揭示了一种制备化学式1所示颜料的方法，其中Y为氢原子或溴原子，n为0、1、2、3或4的整数，R1为烷基或芳基烷基，R2为烷基、芳基、芳基烷基或烷基芳基，R4为烷基、芳基、芳基烷基或烷基芳基。该方法包括以下步骤：(a)通过混合(1)白酚喹啉和可选的喹啉，(2)带有醇基的氨基苯的化合物，其化学式为-R1-OH，(3)硼酸和(4)可选的溶剂来制备第一反应混合物，然后加热第一反应混合物以制备化学式2的醇基取代的颜料；(b)将所制备的颜料转化为酯基取代的颜料，方法为与酯化化合物(A)化学式3的酐或(B)化学式R2COOH的酸在可选的酯化催化剂的存在下反应，或与化学式R4-N=C=O的异氰酸酯化合物反应以制备脲基取代的颜料；(c)溴化所制备的颜料，其中酯化或脲化可以在溴化之前进行，也可以在溴化之后进行。
• Peptide nanofibers decorated with Pd nanoparticles to enhance the catalytic activity for C–C coupling reactions in aerobic conditions
  作者：Indrajit Maity、Dnyaneshwar B. Rasale、Apurba K. Das

  DOI：10.1039/c3ra44787a

  日期：——

  We report the synergistic effects of peptide nanofibers decorated with Pd nanoparticles to enhance the catalytic activity for C–C coupling reactions in mild and aerobic conditions.

  我们报告了肽纳米纤维与钯纳米颗粒的协同作用，以提高温和有氧条件下 CâC 偶联反应的催化活性。
• METHOD FOR PRODUCING BIARYL COMPOUND
  申请人：Sato Koichi

  公开号：US20100087680A1

  公开（公告）日：2010-04-08

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种制备双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱的存在下，将芳香有机化合物与选自芳香基有机硼化合物和硼氧化物化合物组的至少一种化合物反应。