7-氯-2-异丁基-4H-苯并[d][1,3]恶嗪-4-酮 | 587881-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 7-氯-2-异丁基-4H-苯并[d][1,3]恶嗪-4-酮
• 英文名称: 7-chloro-2-isobutyl-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-Chloro-2-isobutyl-benzo[d][1,3]oxazin-4-one；7-chloro-2-(2-methylpropyl)-3,1-benzoxazin-4-one
• CAS: 587881-22-9
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: ZLJKQVHHHZNZDL-UHFFFAOYSA-N

物化性质

• 沸点：
  360.8±44.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-氯-2-异丁基-4H-苯并[d][1,3]恶嗪-4-酮 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 3-苄基-2-(1-溴-2-甲基丙基)-7-氯喹唑啉-4-酮
  参考文献：
  名称：

  Fluorinated quinazolinones as potential radiotracers for imaging kinesin spindle protein expression

  摘要：

  Anti-mitotic anti-cancer drugs offer a potential platform for developing new radiotracers for imaging proliferation markers associated with the mitosis-phase of the cell-cycle. One interesting target is kinesin spindle protein (KSP)-an ATP-dependent motor protein that plays a vital role in bipolar spindle formation. In this work we synthesised a range of new fluorinated-quinazolinone compounds based on the structure of the clinical candidate KSP inhibitor, ispinesib, and investigated their properties in vitro as potential anti-mitotic agents targeting KSP expression. Anti-proliferation (MTT and BrdU) assays combined with additional studies including fluorescence-assisted cell sorting (FACS) analysis of cell-cycle arrest confirmed the mechanism and potency of these biphenyl compounds in a range of human cancer cell lines. Additional studies using confocal fluorescence microscopy showed that these compounds induce M-phase arrest via monoaster spindle formation. Structural studies revealed that compound 20-(R) is the most potent fluorinated-quinazolinone inhibitor of KSP and represents a suitable lead candidate for further studies on designing F-18-radiolabelled agents for positron-emission tomography (PET). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.013
• 作为产物：
  描述：

  4-chloro-2-[(3-methyl-1-oxobutyl)amino]Benzoic acid 在 乙酸酐 作用下， 反应 2.0h， 以86%的产率得到7-氯-2-异丁基-4H-苯并[d][1,3]恶嗪-4-酮
  参考文献：
  名称：

  WO2006/125555

  摘要：

  公开号：

文献信息

• Syntheses of quinazolinones
  申请人：——

  公开号：US20040067969A1

  公开（公告）日：2004-04-08

  The present invention provides intermediates, synthetic methods and novel quinazolinone compositions of matter.

  本发明提供了中间体、合成方法和新型喹唑啉酮组合物。
• Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones
  作者：Ji-Feng Liu、Jaekyoo Lee、Audra M. Dalton、Grace Bi、Libing Yu、Carmen M. Baldino、Eric McElory、Matt Brown

  DOI：10.1016/j.tetlet.2005.01.008

  日期：2005.2

  A practical synthesis of 2,3-disubstituted 3H-quinazolin-4-ones 1 with broad chemistry scope is described. The key step is the microwave promoted one-pot, two-step reaction sequence combining anthranilic acids, carboxylic acids, and amines providing efficient access to this important class of heterocycles. (C) 2005 Elsevier Ltd. All rights reserved.
• SYNTHESES OF QUINAZOLINONES
  申请人：Cytokinetics, Inc.

  公开号：EP1480980A2

  公开（公告）日：2004-12-01
• EP1480980A4
  申请人：——

  公开号：EP1480980A4

  公开（公告）日：2005-04-20
• Quinazolinones
  申请人：Buchstaller Hans-Peter

  公开号：US20080234299A1

  公开（公告）日：2008-09-25

  Compounds of the formula (I), in which R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Z 1 , Z 2 , Z 3 , k and Y 1 have the meanings indicated in claim 1 , can be employed, inter alia, for the treatment of tumours.