(±)-tert-butyl (3-((1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl)amino)propyl)carbamate | 1314917-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (±)-tert-butyl (3-((1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl)amino)propyl)carbamate
• 英文别名: tert-butyl (3-((1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl)amino)propyl)carbamate；{3-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester；tert-butyl N-[3-[[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-methylpropyl]amino]propyl]carbamate
• CAS: 1314917-40-2
• 化学式: C₂₇H₃₅ClN₄O₃
• 分子量: 499.053
• InChiKey: HUFIPLWJKMMYKJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (±)-tert-butyl (3-((1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl)amino)propyl)carbamate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 N-(3-aminopropyl)-N-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-methylpropyl]-2-fluorobenzamide
  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：

  3-苄基-2-(1-溴-2-甲基丙基)-7-氯喹唑啉-4-酮 在 sodium azide 、 三乙酰氧基硼氢化钠 、 氯化铵 、 锌 作用下， 以 甲醇 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 (±)-tert-butyl (3-((1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl)amino)propyl)carbamate
  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

文献信息

• Imides: forgotten players in the Ugi reaction. One-pot multicomponent synthesis of quinazolinones
  作者：Riccardo Mossetti、Tracey Pirali、Dèsirèe Saggiorato、Gian Cesare Tron

  DOI：10.1039/c1cc12067k

  日期：——

  Up to now, the synthesis of quinazolinones has required lengthy synthetic procedures. Here, we describe an innovative one-pot multicomponent reaction leading to highly substituted quinazolinones. We believe that this novel transformation may open the door for the generation of new and pharmacologically active quinazolinones, but, most important of all, the resurrection of the imide-Ugi scaffold paves the way for the synthesis of novel molecular architectures

  迄今为止，喹唑啉酮的合成需要冗长的合成程序。在这里，我们描述了一种创新的一锅多组分反应，可以生成高度取代的喹唑啉酮。我们相信这种新颖的转化可能为新型药理活性喹唑啉酮的产生铺平道路，但最重要的是，酰亚胺-Ugi框架的复兴为新型分子结构的合成开辟了道路。
• 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。
• 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
• US7009049B2
  申请人：——

  公开号：US7009049B2

  公开（公告）日：2006-03-07