2,7-dimethoxyacridine-9-carbaldehyde | 1233355-48-0

• 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: 2,7-dimethoxyacridine-9-carbaldehyde
• CAS: 1233355-48-0
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: ZOOHTYPKZAGOLX-UHFFFAOYSA-N

物化性质

• 沸点：
  481.0±25.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,7-dimethoxyacridine-9-carbaldehyde 在 palladium on activated charcoal 三乙基硅烷 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 LDN-209973
  参考文献：
  名称：

  [EN] ACRIDINES AS INHIBITORS OF HASPIN AND DYRK KINASES
  [FR] ACRIDINES EN TANT QU'INHIBITEURS DES KINASES HASPINE ET DYRK

  摘要：

  公开号：

  WO2011127406A3
• 作为产物：
  描述：

  4,4'-二甲氧基二苯胺 在 indium(III) chloride 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,7-dimethoxyacridine-9-carbaldehyde
  参考文献：
  名称：

  [EN] ACRIDINES AS INHIBITORS OF HASPIN AND DYRK KINASES
  [FR] ACRIDINES EN TANT QU'INHIBITEURS DES KINASES HASPINE ET DYRK

  摘要：

  公开号：

  WO2011127406A3

文献信息

• Structure–activity relationship study of acridine analogs as haspin and DYRK2 kinase inhibitors
  作者：Gregory D. Cuny、Maxime Robin、Natalia P. Ulyanova、Debasis Patnaik、Valerie Pique、Gilles Casano、Ji-Feng Liu、Xiangjie Lin、Jun Xian、Marcie A. Glicksman、Ross L. Stein、Jonathan M.G. Higgins

  DOI：10.1016/j.bmcl.2010.04.150

  日期：2010.6

  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.
• [EN] ACRIDINES AS INHIBITORS OF HASPIN AND DYRK KINASES<br/>[FR] ACRIDINES EN TANT QU'INHIBITEURS DES KINASES HASPINE ET DYRK
  申请人：BRIGHAM & WOMENS HOSPITAL

  公开号：WO2011127406A3

  公开（公告）日：2012-01-26