N¹-(6-chloro-2-methoxyacridin-9-yl)-N⁴,N⁴-dimethylbenzene-1,4-diamine

• 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: N¹-(6-chloro-2-methoxyacridin-9-yl)-N⁴,N⁴-dimethylbenzene-1,4-diamine
• 英文别名: N'-(6-chloro-2-methoxy-acridin-9-yl)-N,N-dimethyl-p-phenylenediamine；N'-(6-Chlor-2-methoxy-acridin-9-yl)-N,N-dimethyl-p-phenylendiamin；1-N-(6-chloro-2-methoxyacridin-9-yl)-4-N,4-N-dimethylbenzene-1,4-diamine
• 化学式: C₂₂H₂₀ClN₃O
• 分子量: 377.873
• InChiKey: OBCKMAZMNQBZOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,9-二氯-2-甲氧基吖啶 、 N,N-二甲基-对苯二胺 在 苯酚 作用下， 反应 0.75h， 以94%的产率得到N¹-(6-chloro-2-methoxyacridin-9-yl)-N⁴,N⁴-dimethylbenzene-1,4-diamine
  参考文献：
  名称：

  微波辐射下无溶剂和无色谱的π缺陷氮杂环胺化反应。快速，高效和绿色的9-氨基ac啶，4-氨基喹啉和4-氨基喹唑啉路线及其在合成氨酚和双胍中的应用

  摘要：

  在2当量苯酚的存在下，用胺对9-氯ac啶，4-氯喹啉和4-氯喹唑啉等分子混合物与胺进行聚焦微波辐照，可以实现胺化杂环的一般，快速和高产率合成，胺结构（芳族，线性伯脂肪族，α-支化伯脂肪族，仲脂肪族和二胺）。后处理包括简单的水洗和结晶纯化，避免在萃取和色谱纯化步骤中使用有机溶剂。该协议为解决长期合成问题提供了解决方案，该问题实现了一种实用有效的方法来胺化π不足的氮杂环以用于药物化学应用。

  DOI：

  10.1016/j.tet.2012.11.083

文献信息

• Burckhalter et al., Journal of the American Chemical Society, 1943, vol. 65, p. 2013
  作者：Burckhalter et al.

  DOI：——

  日期：——
• Antiprion activity of functionalized 9-aminoacridines related to quinacrine
  作者：Hanh Thuy Nguyen Thi、Chong-Yew Lee、Kenta Teruya、Wei-Yi Ong、Katsumi Doh-ura、Mei-Lin Go

  DOI：10.1016/j.bmc.2008.05.060

  日期：2008.7

  A library of functionalized 6-chloro-2-methoxy-(N-9-substituted) acridin-9-amines structurally related to quinacrine were synthesized and evaluated for antiprion activity on four different cell models persistently infected with scrapie prion strains (ScN2a, N167, Ch2) or a human disease prion strain (F3). Most of the compounds were distinguished by the side chain attached to 9-amino of the acridine ring. These were dialkylaminoalkyl and phenyl with basic groups on the phenyl ring. The most promising compound was 6-chloro-2-methoxy-N-(4-(4-methylpiperazin-1-yl) phenyl) acridin-9-amine (15) which had submicromolar EC50 values (0.1-0.7 mu M) on all cell models, was able to clear PrPSc at non-toxic concentrations of 1.2-2.5 mu M, and was more active than quinacrine in terms of EC50 values. Other promising compounds were 14 (a regioisomer of 15) and 17 which had a 1-benzylpiperidin-4-yl substituent attached to the 9-amino function. Activity was strongly dependent on the presence of a substituted acridine ring, which in this library comprised 6-chloro-2-methoxy substituents on the acridine ring. The side chains of 14, 15, and 17 have not been previously associated with antiprion activity and are interesting leads for further optimization of antiprion activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
  作者：Matteo Staderini、Nieves Cabezas、Maria Laura Bolognesi、J. Carlos Menéndez

  DOI：10.1016/j.tet.2012.11.083

  日期：2013.1

  very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic

  在2当量苯酚的存在下，用胺对9-氯ac啶，4-氯喹啉和4-氯喹唑啉等分子混合物与胺进行聚焦微波辐照，可以实现胺化杂环的一般，快速和高产率合成，胺结构（芳族，线性伯脂肪族，α-支化伯脂肪族，仲脂肪族和二胺）。后处理包括简单的水洗和结晶纯化，避免在萃取和色谱纯化步骤中使用有机溶剂。该协议为解决长期合成问题提供了解决方案，该问题实现了一种实用有效的方法来胺化π不足的氮杂环以用于药物化学应用。