3-benzyl-7-chloro-2-(2-methylpropyl)-3,4-dihydroquinazolin-4-one | 587881-23-0

• 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: 3-benzyl-7-chloro-2-(2-methylpropyl)-3,4-dihydroquinazolin-4-one
• 英文别名: 3-benzyl-7-chloro-2-isobutylquinazolin-4(3H)-one；3-benzyl-7-chloro-2-(2-methylpropyl)quinazolin-4-one
• CAS: 587881-23-0
• 化学式: C₁₉H₁₉ClN₂O
• 分子量: 326.826
• InChiKey: RVBSKDCINWYUOU-UHFFFAOYSA-N

物化性质

• 沸点：
  486.5±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-benzyl-7-chloro-2-(2-methylpropyl)-3,4-dihydroquinazolin-4-one 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 反应 4.0h， 以97%的产率得到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：

  异戊酸 在 亚磷酸三苯酯 作用下， 以 吡啶 为溶剂， 反应 0.17h， 生成 3-benzyl-7-chloro-2-(2-methylpropyl)-3,4-dihydroquinazolin-4-one
  参考文献：
  名称：

  Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.01.008

文献信息

• Syntheses of quinazolinones from 2-iodobenzamides and enaminones via copper-catalyzed domino reactions
  作者：Teerawat Songsichan、Jaturong Promsuk、Vatcharin Rukachaisirikul、Juthanat Kaeobamrung

  DOI：10.1039/c4ob00400k

  日期：——

  N-Substituted 2-iodobenzamides and enaminones undergo cascade transformations to achieve quinazolinones via a copper-catalyzed Ullmann-type coupling, a Michael addition and a retro-Mannich reaction. A unique stereochemical feature of this domino process was that Z-enaminones reacted without external ligands, whereas E-enaminones required the assistance of ligands.

  N-取代的2-碘苯甲酰胺和烯胺酮通过级联转化实现喹唉酮的合成，这一过程包括铜催化的乌尔曼型偶联反应、迈克尔加成反应和逆曼尼希反应。该多米诺反应的独特立体化学特征在于，Z-烯胺酮无需外部配体即可反应，而E-烯胺酮则需要配体的辅助。
• 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。
• METHOD FOR SCREENING COMPOUND FOR TREATING OR PREVENTING POLYQ-RELATED NEURODEGENERATIVE DISEASES
  申请人：Fudan University

  公开号：EP3940384A1

  公开（公告）日：2022-01-19

  The present invention relates to a method for screening or identifying compound(s) for the treatment or prevention of a polyQ-related neurodegenerative disorder, and the compounds obtained by the method and uses thereof.

  本发明涉及一种筛选或鉴定用于治疗或预防多 Q 相关神经退行性疾病的化合物的方法，以及通过该方法获得的化合物及其用途。
• WO2006/125555
  申请人：——

  公开号：——

  公开（公告）日：——
• SYNTHESES OF QUINAZOLINONES
  申请人：Cytokinetics, Inc.

  公开号：EP1480980A2

  公开（公告）日：2004-12-01