2-methoxy-10H-acridine-9-thione | 21516-39-2

• 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-10H-acridine-9-thione
• 英文别名: 2-Methoxy-10H-acridin-9-thion；2-methoxy-acridane-9-thione；2-Methoxy-thio-acridon-(9)；Lbdmftsefyrpqz-uhfffaoysa-；2-methoxy-10H-acridine-9-thione
• CAS: 21516-39-2
• 化学式: C₁₄H₁₁NOS
• 分子量: 241.313
• InChiKey: LBDMFTSEFYRPQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  232-233.5 °C
• 沸点：
  420.7±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-10H-acridine-9-thione 、 3-溴丙胺氢溴酸盐 在 苯酚 作用下， 生成 LDN-209856
  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-methoxy-9(10H)-acridinone 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 生成 2-methoxy-10H-acridine-9-thione
  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

• Poulallion, Pierre; Galy, Jean-Pierre; Vincent, Emile-Jean, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1141 - 1149
  作者：Poulallion, Pierre、Galy, Jean-Pierre、Vincent, Emile-Jean、Galy, Anne-Marie、Barbe, Jacques、Atassi, Ghanem

  DOI：——

  日期：——
• Synthesis and biological properties of derivatives of 4-heterylmercaptoquinazoline
  作者：R. S. Sinyak、I. A. Mazur、V. R. Smets、A. A. Martynovskii、P. N. Steblyuk

  DOI：10.1007/bf00766901

  日期：1986.2
• Tschernzow, Zhurnal Obshchei Khimii, 1944, vol. 14, p. 186,192
  作者：Tschernzow

  DOI：——

  日期：——
• Das-Gupta, Journal of the Indian Chemical Society, 1940, vol. 17, p. 246
  作者：Das-Gupta

  DOI：——

  日期：——
• MARTYNOVSKIJ, A. A.;KLYUEV, N. A.;KURAPOV, P. B.;MELNIK, I. V.;PANASENKO,+, IZV. TIMIRYAZEV. S.-X. AKAD.,(1989) N, S. 157-165
  作者：MARTYNOVSKIJ, A. A.、KLYUEV, N. A.、KURAPOV, P. B.、MELNIK, I. V.、PANASENKO,+

  DOI：——

  日期：——

表征谱图