2-Methoxy-9-phenoxy-acridin | 61078-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-Methoxy-9-phenoxy-acridin
• 英文别名: 2-Methoxy-9-phenoxyacridine
• CAS: 61078-20-4
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: XAJLYOUHZAGPLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxy-9-phenoxy-acridin 在 碳酸氢铵 、 苯酚 作用下， 反应 0.75h， 以1.03 g的产率得到2-甲氧基吖啶-9-胺
  参考文献：
  名称：

  Frameshift Mutagenicity and DNA Intercalation of 9-Amino-2-hydroxyacridine, a Rat Liver S9 Metabolite of 9-Aminoacridine

  摘要：

  合成了 9-氨基吖啶（9-AA）的大鼠肝脏 S9 代谢物--9-氨基-2-羟基吖啶，并发现它比 9-AA 具有更低的帧移诱变性和更强的 DNA 结合亲和力。

  DOI：

  10.1271/bbb.60.714
• 作为产物：
  描述：

  2-溴苯甲酸 在 铜 、 potassium carbonate 、 三氯氧磷 作用下， 以 异戊醇 为溶剂， 反应 7.0h， 生成 2-Methoxy-9-phenoxy-acridin
  参考文献：
  名称：

  Wysocka-Skrzela, Barbara; Cholody, Wieslaw M.; Ledochowski, Andrzej, Polish Journal of Chemistry, 1981, vol. 55, # 10, p. 2211 - 2214

  摘要：

  DOI：

文献信息

• Synthesis of Monomeric and Dimeric Acridine Compounds as Potential Therapeutics in Alzheimer and Prion Diseases
  作者：René Csuk、Alexander Barthel、Christian Raschke、Ralph Kluge、Dieter Ströhl、Lothar Trieschmann、Gerald Böhm

  DOI：10.1002/ardp.200900065

  日期：2009.12

  spacered dimeric acridine compounds was prepared. Their ability to interrupt the protein association of prion‐ and Alzheimer‐specific proteins and Ab peptides was explored using a fast screening system based on FACS analysis. The bis‐acridines displayed a higher activity than the corresponding monomers. Among these derivatives, best results were obtained with the 2,4‐dimethoxy‐6‐nitro compound 7h for

  从取代的 9-氯吖啶开始，制备了一系列奎纳克林和间隔二聚吖啶化合物。使用基于 FACS 分析的快速筛选系统探索了它们中断朊病毒和阿尔茨海默特异蛋白与 Ab 肽的蛋白质结合的能力。双吖啶比相应的单体表现出更高的活性。在这些衍生物中，Aβ-肽的 2,4-二甲氧基-6-硝基化合物 7h 和 PrP 的 2-甲氧基-6-硝基化合物 7f 获得了最好的结果。
• Drosdow, Zhurnal Obshchei Khimii, 1936, vol. 6, p. 1641,1643
  作者：Drosdow

  DOI：——

  日期：——
• Synthesis and DNA-sequence selectivity of a series of mono- and difunctional 9-aminoacridine nitrogen mustards
  作者：Kurt W. Kohn、Ann Orr、Patrick M. O'Connor、Lynn James Guziec、Frank S. Guziec

  DOI：10.1021/jm00027a008

  日期：1994.1

  The aim of this work was to identify nitrogen mustards that would react selectively with DNA, particularly in G-rich regions. A sei ies of mono- and difunctional nitrogen mustards was synthesized in which the (2-chloroethyl)amino functions were connected to the N-9 of 9-aminoacridine by way of a spacer chain consisting of two to six methylene units. The length of the spacer chain connecting the alkylating and putative DNA-intercalating groups was found to affect the preference for the alkylation of different guanine-N-7 positions in a DNA sequence. All of the compounds reacted preferentially at G's that are followed by G as do most other types of nitrogen mustards, but the degree of selectivity was greater. The compounds reacted at much lower concentrations than were required for comparable reaction by mechlorethamine (HN2), consistent with initial noncovalent binding to DNA prior to guanine-N-7 alkylation. The degree of DNA-sequence selectivity increased as the spacer-chain length decreased below four methylene units. Most strikingly, long spacer compounds reacted strongly at 5'-GT-3' sequences, Whereas this reaction was almost completely suppressed when-the spacer length was reduced to two or three methylenes. Mono- and difunctional compounds of a given spacer length showed no consistent difference in DNA-sequence preference.
• Drosdow, Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2292,2295
  作者：Drosdow

  DOI：——

  日期：——
• 339. Attempts to find new antimalarials. Part XV. The synthesis of acridine compounds related to atebrin
  作者：Robert R. Goodall、William O. Kermack

  DOI：10.1039/jr9360001546

  日期：——