6,9-dichloro-2-methoxyacridine | 16710-31-9

• 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: 6,9-dichloro-2-methoxyacridine
• 英文别名: 2,9-dichloro-6-methoxyacridine；3-Methoxy-7,9-dichlor-acridin；2,9-Dichlor-6-methoxy-acridin
• CAS: 16710-31-9
• 化学式: C₁₄H₉Cl₂NO
• 分子量: 278.138
• InChiKey: AONZVSKXEVFZBG-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C(Solv: benzene (71-43-2))
• 沸点：
  434.6±25.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,9-dichloro-2-methoxyacridine 在 3 A molecular sieve 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 N,N-diethyl-N'-(2-chloro-6-methoxy-acridin-9-yl)-propanediyldiamine
  参考文献：
  名称：

  Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

  摘要：

  A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.017
• 作为产物：
  描述：

  2,5-二氯苯甲酸 在 三氯氧磷 作用下， 生成 6,9-dichloro-2-methoxyacridine
  参考文献：
  名称：

  Singh et al., Journal of the Indian Chemical Society, 1951, vol. 28, p. 698,700

  摘要：

  DOI：

文献信息

• A Convenient Procedure for Parallel Ester Hydrolysis
  作者：R. Kiplin Guy、Marc O. Anderson、Jamie Moser、John Sherrill

  DOI：10.1055/s-2004-832828

  日期：——

  The treatment of alkyl esters with barium hydroxide ­octahydrate in methanol followed by protonation with anhydrous hydrogen chloride affords carboxylic acids. The procedure does not require aqueous workup and is particularly suitable for parallel ­synthesis applications.

  用八水合氢氧化钡处理烷基酯并在甲醇中用无水氢氯酸质子化，可以得到羧酸。该方法无需水洗处理，特别适用于并行合成应用。
• Labeling Deoxyadenosine for the Preparation of Functional Conjugated Oligonucleotides
  作者：Massimo L. Capobianco、Elena Marchesi、Daniela Perrone、Maria Luisa Navacchia

  DOI：10.1021/bc400243q

  日期：2013.8.21

  carbon linker having on the other side a variety of molecules (psoralen, acridine) and functional groups (alkyne). After conventional protections, the modified adenosine can be phosphytylated and inserted into an oligonucleotide without affecting the standard protocols for supported oligonucleotide synthesis. The hybridization properties of a generic oligonucleotide containing the above conjugated moieties

  本文中，我们提出了一种通用的合成方法，该方法用于在短侧具有短链接头的（脱氧）腺苷的8-硫代烷基化反应，所述短链接头在另一侧具有多种分子（补骨脂素，a啶）和官能团（炔烃）。在常规保护之后，可以将修饰的腺苷磷酸化并插入寡核苷酸中，而不会影响支持的寡核苷酸合成的标准方案。在完全互补的链的情况下和在单个错配的情况下，都评估了包含上述缀合部分的对DNA和RNA两者的通用寡核苷酸的杂交性质。这种方法学适合于制备几种类型的衍生物，并且通过炔基部分，可快速获得点击化学转化。
• The synthesis and evaluation of o-phenylenediamine derivatives as fluorescent probes for nitric oxide detection
  作者：M. John Plater、Iain Greig、Miep H. Helfrich、Stuart H. Ralston

  DOI：10.1039/b105953j

  日期：2001.10.11

  A series of molecular probes for the determination of nitric oxide (NO) have been prepared. Each probe consists of an anthracene, coumarin or acridine fluorophore coupled to an electron rich o-phenylenediamine group. The o-phenylenediamine group can be substituted with methyl or methoxy groups to enhance its electron rich nature. The fluorophore fluorescence is quenched by photoelectron transfer (PET) from the aromatic amine to the lowest unoccupied orbital of the excited state fluorophore. Reaction with nitrosating species converts the o-phenylenediamine group into an electron deficient benzotriazole derivative. This group has a higher oxidation potential and does not quench the fluorophore fluorescence by photoelectron transfer so that these products are highly fluorescent. Some benzotriazole derivatives were made preparatively by alternative synthetic routes. The formation of fluorescent probes was evaluated by treatment of the precursors with nitrous fumes and S-nitroso-N-acetylpenicillamine (SNAP).

  制备了一系列用于测定一氧化氮（NO）的分子探针。每个探针由与富电子邻苯二胺基团偶联的蒽、香豆素或吖啶荧光团组成。邻苯二胺基团可以被甲基或甲氧基取代以增强其富电子性质。通过从芳香胺到激发态荧光团的最低未占据轨道的光电子转移（PET），荧光团荧光被淬灭。与亚硝化物质的反应将邻苯二胺基团转化为缺电子苯并三唑衍生物。该基团具有较高的氧化电位，并且不会通过光电子转移猝灭荧光团的荧光，因此这些产品具有高荧光性。一些苯并三唑衍生物是通过替代合成路线制备的。通过用亚硝酸处理前体来评估荧光探针的形成 烟雾和 S-亚硝基-N-乙酰青霉胺 (SNAP)。
• Singh et al., Journal of the Indian Chemical Society, 1951, vol. 28, p. 459,463
  作者：Singh et al.

  DOI：——

  日期：——
• Addition Reactions of 1-Cyano-1,3-butadiene^1,2
  作者：Milton Frankel、Harry S. Mosher、Frank C. Whitmore

  DOI：10.1021/ja01157a023

  日期：1950.1