4-[(4-methoxyphenyl)diazenyl]aniline | 2592-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-[(4-methoxyphenyl)diazenyl]aniline
• 英文别名: (E)-4-((4-methoxyphenyl)diazenyl)aniline；4-Methoxy-4'-aminoazobenzol；4-amino-4'-methoxy-azobenzene；4'-Methoxy-4-aminoazobenzene
• CAS: 2592-28-1
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: ISTLPRFJQOIQMU-FOCLMDBBSA-N

物化性质

• 沸点：
  336.78°C (rough estimate)
• 密度：
  1.0671 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.97
• 氢给体数：
  1.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  4-[(4-methoxyphenyl)diazenyl]aniline 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(E)-2-chloro-N-(4-((4-methoxyphenyl)diazenyl)phenyl)acetamide
  参考文献：
  名称：

  Reversible Photocontrolled Nanopore Assembly

  摘要：

  Self-assembly is a fundamental feature of biological systems, and control of such processes offers fascinating opportunities to regulate function. Fragaceatoxin C (FraC) is a toxin that upon binding to the surface of sphingomyelin-rich cells undergoes a structural metamorphosis, leading to the assembly of nanopores at the cell membrane and causing cell death. In this study we attached photoswitchable azobenzene pendants to various locations near the sphingomyelin binding pocket of FraC with the aim of remote controlling the nanopore assembly using light. We found several constructs in which the affinity of the toxin for biological membranes could be activated or deactivated by irradiation, thus enabling reversible photocontrol of pore formation. Notably, one construct was completely inactive in the thermally adapted state; it however induced full lysis of cultured cancer cells upon light irradiation. Selective irradiation also allowed isolation of individual nanopores in artificial lipid membranes. Photocontrolled FraC might find applications in photopharmacology for cancer therapeutics and has potential to be used for the fabrication of nanopore arrays in nanopore sensing devices, where the reconstitution, with high spatiotemporal precision, of single nanopores must be controlled.

  DOI：

  10.1021/jacs.9b06998
• 作为产物：
  描述：

  (E)-1-(4-methoxyphenyl)-2-(4-nitrophenyl)diazene 在 hydrazine hydrate 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以60%的产率得到4-[(4-methoxyphenyl)diazenyl]aniline
  参考文献：
  名称：

  Reversible Photocontrolled Nanopore Assembly

  摘要：

  Self-assembly is a fundamental feature of biological systems, and control of such processes offers fascinating opportunities to regulate function. Fragaceatoxin C (FraC) is a toxin that upon binding to the surface of sphingomyelin-rich cells undergoes a structural metamorphosis, leading to the assembly of nanopores at the cell membrane and causing cell death. In this study we attached photoswitchable azobenzene pendants to various locations near the sphingomyelin binding pocket of FraC with the aim of remote controlling the nanopore assembly using light. We found several constructs in which the affinity of the toxin for biological membranes could be activated or deactivated by irradiation, thus enabling reversible photocontrol of pore formation. Notably, one construct was completely inactive in the thermally adapted state; it however induced full lysis of cultured cancer cells upon light irradiation. Selective irradiation also allowed isolation of individual nanopores in artificial lipid membranes. Photocontrolled FraC might find applications in photopharmacology for cancer therapeutics and has potential to be used for the fabrication of nanopore arrays in nanopore sensing devices, where the reconstitution, with high spatiotemporal precision, of single nanopores must be controlled.

  DOI：

  10.1021/jacs.9b06998

文献信息

• Azofarbstoffe
  申请人：BAYER AG

  公开号：EP0097289A2

  公开（公告）日：1984-01-04

  Die vorliegende Erfindung betrifft neue Azofarbstoffe der allgemeinen Formel mit der Maßgabe, daß die Reste D-N=N- und -OH in ortho- Stellung zueinander stehen. Die Erfindung betrifft weiterhin Metallkomplexe der Azofarbstoffe (1). Für Formel (1) gilt: D = aromatisch carbocyclischer oder aromatisch heterocyclischer Rest, R = H oder SO3H, R1 = H oder C,-C4-Alkyl, wobei Y = -NO2, -NH2 oder -NH-Z Z = faserreaktiver Rest oder nichtfaserreaktiver Carbonyl- oder Sulfonylrest. Die Erfindung betrifft weiterhin die für die Herstellung von Azofarbstoffen (1) geeigneten neuen Naphtholamin-Derivate der Formel worin R = H oder S03H R, = H oder C1-C4-Alkyl

  本发明涉及通式为 的新偶氮染料，其限制条件是自由基 D-N=N- 和 -OH 互为正交位置。 本发明还涉及偶氮染料（1）的金属络合物。以下内容适用于式（1）： D = 芳香碳环或芳香杂环基、 R = H 或 SO3H、 R1 = H 或 C,-C4-烷基、 其中 Y = -NO2、-NH2 或 -NH-Z Z = 纤维反应基或非纤维反应羰基或磺酰基。 本发明还涉及适用于制备式（1）偶氮染料的新萘胺衍生物 式中 R = H 或 S03H R, = H 或 C1-C4- 烷基
• Naphtolamin-Derivate
  申请人：BAYER AG

  公开号：EP0177978A2

  公开（公告）日：1986-04-16

  VerbindungenderFormel in der R, H oder SO3H, R1, H oder C1-C4-Alkyl und X1 bezeichnen, sowie die Verbindung der Formel sind wertvolle Zwischenprodukte zur Herstellung von Farbstoffen.

  式中 R 表示 H 或 SO3H，R1 表示 H 或 C1-C4 烷基，X1 和式中化合物是生产着色剂的重要中间体。
• REVERSIBLE PHOTO-CONTROLLED FRAC NANOPORES, MODIFIED FRAC MONOMERS, METHODS FOR PREPARING THE SAME, AND USES THEREOF
  申请人：RIJKSUNIVERSITEIT GRONINGEN

  公开号：EP3771687A1

  公开（公告）日：2021-02-03

  The invention relates to the fields of photopharmacology and photo-controlled analyte sensing. More in particular, it relates to a pore forming toxin Fragaceatoxin C (FraC) from Actina fragacea that can be reversibly controlled by using light as external trigger. Provided is a modified FraC monomer capable of forming a photo-controlled FraC nanopore, the FraC monomer comprising a photoswitchable moiety, e.g. an azobenzene-based photoswitch, covalently attached to one or more of the positions K77, W112, E134, Y138, and S166.

  本发明涉及光药理学和光控分析物传感领域。更具体地说，本发明涉及一种可通过使用光作为外部触发器进行可逆控制的孔隙形成毒素 Fragaceatoxin C（FraC）。本发明提供了一种能够形成光控 FraC 纳米孔的改性 FraC 单体，该 FraC 单体包括共价连接到 K77、W112、E134、Y138 和 S166 位置中的一个或多个位置的可光开关分子，例如偶氮苯基光开关。
• Biskationische Azofarbstoffe sowie deren Zwischenprodukte
  申请人：BASF Aktiengesellschaft

  公开号：EP0482508B1

  公开（公告）日：1995-07-12
• Disazo dye for thermal transfer recording, and thermal transfer sheet and ink for thermal transfer recording, employing it
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1013718B1

  公开（公告）日：2003-06-04