4,4′-bis-[1,1′-biphenyl]-4,4′-diylbis(diazene-2,1-diyl)diphenol | 4998-22-5

• 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: 4,4′-bis-[1,1′-biphenyl]-4,4′-diylbis(diazene-2,1-diyl)diphenol
• 英文别名: 4-[[4-[4-[(4-Hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]phenol
• CAS: 4998-22-5
• 化学式: C₂₄H₁₈N₄O₂
• 分子量: 394.433
• InChiKey: CHPPCFXSZAQCHS-UHFFFAOYSA-N

物化性质

• 沸点：
  664.2±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4′-bis-[1,1′-biphenyl]-4,4′-diylbis(diazene-2,1-diyl)diphenol 生成 4,4'-Bis-(4-phenylacetoxy-phenylazo)-biphenyl
  参考文献：
  名称：

  Vorlaender, Chemische Berichte, 1937, vol. 70, p. 1202,1210

  摘要：

  DOI：
• 作为产物：
  描述：

  联苯胺 在 盐酸 作用下， 生成 4,4′-bis-[1,1′-biphenyl]-4,4′-diylbis(diazene-2,1-diyl)diphenol
  参考文献：
  名称：

  Schultz; Ichenhaeuser, Journal fur praktische Chemie (Leipzig 1954), 1908, vol. <2> 77, p. 114

  摘要：

  DOI：

文献信息

• Azo-containing urethane analogues for colonic drug delivery: synthesis, characterization and in-vitro evaluation
  作者：M S Chavan、V P Sant、M S Nagarsenker

  DOI：10.1211/0022357011776063

  日期：2010.2.18

  A urethane-based analogue containing an azo aromatic linkage in the backbone was synthesized for use in colon-specific delivery systems by reacting toluene-2,6-diisocyanate with a mixture of an aromatic azo diol, (bis-4-hydroxyphenyl)-4,4′-diazobiphenyl, poly(ethylene glycol) (Mn = 4000; number-average molecular weight) and 1,2-propanediol (propylene glycol). The resultant compounds (UR-1 and UR-2) were characterized by IR spectroscopy, 1H NMR spectroscopy, DSC studies, X-ray diffraction studies and molecular weight determination by gel permeation chromatography. The compounds exhibited low molecular weight, lacked film-forming properties and crystallinity in the structure. An in-vitro bacterial degradation test to demonstrate the susceptibility of azo bond to bacterial enzymes was performed using media inoculated with lactobacillus culture. The results indicated degradation of films by azoreductase. In-vitro permeation of 5-aminosalicylic acid was studied in control and lactobacilli-treated films. The permeability of the lactobacilli treated films was significantly increased suggesting the potential of these compounds for application in colonic targeting.

  标题：摘要 一种基于脲的类似物，其主链中含有偶氮芳香键，通过将甲苯-2,6-二异氰酸酯与芳香偶氮二酚（双-4-羟基苯基）-4,4'-二偶氮联苯、聚乙二醇（Mn=4000；数均分子量）和1,2-丙二醇（丙二醇）的混合物反应合成，用于结肠特异性传递系统。所得化合物（UR-1和UR-2）通过红外光谱、1H核磁共振光谱、DSC研究、X射线衍射研究和凝胶渗透色谱确定了分子量。这些化合物具有低分子量，缺乏成膜性能和结晶性结构。通过在接种乳杆菌培养基的培养基中进行体外细菌降解试验来展示偶氮键对细菌酶的敏感性。结果表明，偶氮还原酶降解了薄膜。在对照组和乳杆菌处理的薄膜中研究了5-氨基水杨酸的体外渗透性。结果表明，乳杆菌处理的薄膜的渗透性显著增加，表明这些化合物在结肠靶向应用中具有潜力。
• Azo Compound, Composition For Photo-Alignment Film Using The Same, And Method For Producing Photo-Alignment Film
  申请人：Kondo Hitoshi

  公开号：US20070254220A1

  公开（公告）日：2007-11-01

  An azo compound of the present invention is represented by the general formula (1): (wherein, R 1 and R 2 each independently represents a hydroxy group, or a polymerizable functional group selected from the group consisting of a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acrylamide group, a vinyl group, a vinyloxy group, and a maleimide group; X 1 represents single bond when R 1 is a hydroxy group and represents a linking group represented by -(A 1 -B 1 ) m - when R 1 is a polymerizable functional group; X 2 represents a single bond when R 2 is a hydroxy group and represents a linking group represented by -(A 2 -B 2 ) n - when R 2 is a polymerizable functional group; R 3 and R 4 each independently represents —OR 7 , a hydroxyalkyl group having 1 to 4 carbon atoms, or —CONR 8 R 9 ; and R 5 and R 6 each independently represents a carboxy group, a sulfo group, a nitro group, amino group, or a hydroxy group).

  本发明的偶氮化合物由一般式(1)表示：（其中，R1和R2分别独立地表示羟基，或从选自（甲基）丙烯酰基，（甲基）丙烯酰氧基，（甲基）丙烯酰胺基，乙烯基，乙烯氧基和马来酰亚胺基的聚合功能基组成的群体中选择的可聚合功能基组；当R1是羟基时，X1表示单键，并且当R1是可聚合功能基时，X1表示由-(A1-B1)m-表示的连接基；当R2是羟基时，X2表示单键，并且当R2是可聚合功能基时，X2表示由-(A2-B2)n-表示的连接基；R3和R4各自独立地表示-OR7，1至4个碳原子的羟基烷基或CONR8R9；R5和R6各自独立地表示羧基，磺酰基，硝基，氨基或羟基）。
• Design, synthesis, acetylcholinesterase, butyrylcholinesterase, and amyloid‐β aggregation inhibition studies of substituted 4,4ʹ‐diimine/4,4ʹ‐diazobiphenyl derivatives
  作者：Görkem S. Fidan、Sulunay Parlar、Ayse H. Tarikogullari、Vildan Alptuzun、Ayşe S. Alpan

  DOI：10.1002/ardp.202200152

  日期：2022.12

  displayed weak or no BChE inhibition. Among the title compounds, compound 2l, 4,4′-bis(quinolin-8-yldiazenyl)-1,1′-biphenyl, having a diazo-quinoline moiety demonstrated the most potent inhibition against AChE with an IC50 value of 5.77 μM. Furthermore, diazo derivatives 2d, 4,4′-bis[(4-methoxyphenyl)diazenyl]-1,1′-biphenyl, and 2i, 4,4′-bis(pyridin-3-yldiazenyl)-1,1′-biphenyl, provided better potency on Aβ1–42

  设计、合成了一系列 4,4'-二亚胺/4,4'-重氮联苯衍生物，并评估了它们抑制乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BChE) 酶以及 Aβ 1–42聚集的能力,体外。AChE 和 BChE 抑制测定表明，所有化合物在 IC 50  = 5.77–16.22 μM 范围内均显示出中度 AChE 抑制活性，而它们显示出较弱或无 BChE 抑制作用。在标题化合物中，化合物2l , 4,4'-bis(quinolin-8-yldiazenyl)-1,1'-biphenyl, having a diazo-quinoline moiety 证明对 AChE 的抑制作用最强，IC 50值为 5.77 μM . 此外，重氮衍生物2d, 4,4'-bis[(4-methoxyphenyl)diazenyl]-1,1'-biphenyl, and 2i , 4,4'-bis(pyridin-3-yldiazenyl)-1
• Fichter; Jaeck, Helvetica Chimica Acta, 1921, vol. 4, p. 1009
  作者：Fichter、Jaeck

  DOI：——

  日期：——
• Mai; Schwabacher, Chemische Berichte, 1901, vol. 34, p. 3937
  作者：Mai、Schwabacher

  DOI：——

  日期：——