2,9-Dichlor-7-methoxy-acridin | 16710-32-0

• 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: 2,9-Dichlor-7-methoxy-acridin
• 英文别名: 2-Methoxy-7,9-dichlor-acridin；2,9-dichloro-7-methoxy-acridine；2,9-Dichloro-7-methoxyacridine
• CAS: 16710-32-0
• 化学式: C₁₄H₉Cl₂NO
• 分子量: 278.138
• InChiKey: HNIIRXRVBORJNL-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °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：

  2,9-Dichlor-7-methoxy-acridin 在 tetraphosphorus decasulfide 作用下， 以 N,N-二甲基丙烯基脲 为溶剂， 生成
  参考文献：
  名称：

  Structure–activity relationship study of acridine analogs as haspin and DYRK2 kinase inhibitors

  摘要：

  Haspin is a serine/threonine kinase required for completion of normal mitosis that is highly expressed during cell proliferation, including in a number of neoplasms. Consequently, it has emerged as a potential therapeutic target in oncology. A high throughput screen of approximately 140,000 compounds identified an acridine analog as a potent haspin kinase inhibitor. Profiling against a panel of 270 kinases revealed that the compound also exhibited potent inhibitory activity for DYRK2, another serine/threonine kinase. An optimization study of the acridine series revealed that the structure-activity relationship (SAR) of the acridine series for haspin and DYRK2 inhibition had many similarities. However, several structural differences were noted that allowed generation of a potent haspin kinase inhibitor (33, IC(50) <60 nM) with 180fold selectivity over DYRK2. In addition, a moderately potent DYRK2 inhibitor (41, IC(50) <400 nM) with a 5.4-fold selectivity over haspin was also identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.150
• 作为产物：
  描述：

  2-(4-chloro-anilino)-5-methoxy-benzoic acid 在 三氯氧磷 作用下， 生成 2,9-Dichlor-7-methoxy-acridin
  参考文献：
  名称：

  Structure–activity relationship study of acridine analogs as haspin and DYRK2 kinase inhibitors

  摘要：

  Haspin is a serine/threonine kinase required for completion of normal mitosis that is highly expressed during cell proliferation, including in a number of neoplasms. Consequently, it has emerged as a potential therapeutic target in oncology. A high throughput screen of approximately 140,000 compounds identified an acridine analog as a potent haspin kinase inhibitor. Profiling against a panel of 270 kinases revealed that the compound also exhibited potent inhibitory activity for DYRK2, another serine/threonine kinase. An optimization study of the acridine series revealed that the structure-activity relationship (SAR) of the acridine series for haspin and DYRK2 inhibition had many similarities. However, several structural differences were noted that allowed generation of a potent haspin kinase inhibitor (33, IC(50) <60 nM) with 180fold selectivity over DYRK2. In addition, a moderately potent DYRK2 inhibitor (41, IC(50) <400 nM) with a 5.4-fold selectivity over haspin was also identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.150

文献信息

• Drosdow; Lesnowa, Zhurnal Obshchei Khimii, 1935, vol. 5, p. 690,695
  作者：Drosdow、Lesnowa

  DOI：——

  日期：——
• Synthesen in der Acridinreihe. (Die Erforschung von Malariaheilmitteln.)
  作者：J. Ch. Feldman、E. L. Kopeliowitsch

  DOI：10.1002/ardp.19352732910

  日期：——
• Singh; Singh; Singh, Journal of the Indian Chemical Society, 1947, vol. 24, p. 79,81
  作者：Singh、Singh、Singh

  DOI：——

  日期：——
• Drosdow; Tschernzow, Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1736,1739
  作者：Drosdow、Tschernzow

  DOI：——

  日期：——
• Drosdow; Tschernzow, Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1576,1580
  作者：Drosdow、Tschernzow

  DOI：——

  日期：——