3-benzyl-2-(4-(dimethylamino)phenyl)quinazolin-4(3H)-one

• 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-2-(4-(dimethylamino)phenyl)quinazolin-4(3H)-one
• 英文别名: 3-Benzyl-2-(4-dimethylamino-phenyl)-3H-quinazolin-4-one；3-benzyl-2-[4-(dimethylamino)phenyl]quinazolin-4-one
• 化学式: C₂₃H₂₁N₃O
• 分子量: 355.439
• InChiKey: VMLDMNPGGINIGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-二甲氨基苯甲酰氯 在 吡啶 、 硫酸 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 生成 3-benzyl-2-(4-(dimethylamino)phenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Studies on Quinazolinones as Dual Inhibitors of Pgp and MRP1 in Multidrug Resistance

  摘要：

  The syntheses and SAR studies of various quinazolinone compounds are described for the dual inhibition of Pgp and MRP1 in multidrug resistance. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00804-6

文献信息

• Cu/Pd-Catalyzed C-2-H Arylation of ­Quinazolin-4(3<i>H</i>)-ones with (Hetero)aryl Halides
  作者：Julien Godeau、Marine Harari、Sylvain Laclef、Emmanuel Deau、Corinne Fruit、Thierry Besson

  DOI：10.1002/ejoc.201501129

  日期：2015.12

  The regiospecific C-2–H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct cross-coupling with a variety of (hetero)aryl halides. This useful and scalable procedure promotes the construction of C(sp2)–C(sp2) bonds from arenes

  研究了在微波辐射下，N-3-取代的喹唑啉-4（3H）-酮与多种芳基或（杂）芳基卤化物的区域特异性C-2-H芳基化。开发了一种依赖于配体的钯/铜双催化系统，并允许与各种（杂）芳基卤化物直接交叉偶联。这种有用且可扩展的过程促进了从芳烃或（杂）芳烃和芳基或（杂）芳基溴化物和氯化物以一种省时的策略构建 C(sp2)–C(sp2) 键。还研究了使用碘苯将反应扩展到各种 N-3-取代的喹唑啉-4(3H)-酮以及该方法的范围和局限性。
• One-pot, multicomponent synthesis of 2,3-disubstituted quinazolin-ones with potent and selective activity against Toxoplasma gondii
  作者：Carla E. Brown、Tiffany Kong、Claudia Bordón、Robert Yolken、Lorraine Jones-Brando、James McNulty

  DOI：10.1016/j.bmcl.2018.03.036

  日期：2018.5

  The discovery of two quinazolinones with selective, single-digit micromolar activity (IC50 = 6-7 mu M) against the tachyzoites of the apicomplexan parasite Toxoplasma gondii is reported. These potent and selective third generation derivatives contain a benzyloxybenzyl substituent at C2 and a bulky aliphatic moiety at N3. Here we show that these quinazolinones inhibit T. gondii tachyzoite replication in an established infection, but do not significantly affect host cell invasion by the tachyzoites. (C) 2018 Elsevier Ltd. All rights reserved.
• Record material
  申请人：The Wiggins Teape Group Limited

  公开号：EP0145225B1

  公开（公告）日：1989-10-04
• US4587538A
  申请人：——

  公开号：US4587538A

  公开（公告）日：1986-05-06
• Studies on Quinazolinones as Dual Inhibitors of Pgp and MRP1 in Multidrug Resistance
  作者：Shouming Wang、Hamish Ryder、Ian Pretswell、Paul Depledge、John Milton、Timothy C. Hancox、Ian Dale、Wendy Dangerfield、Peter Charlton、Richard Faint、Rory Dodd、Stephanie Hassan

  DOI：10.1016/s0960-894x(01)00804-6

  日期：2002.2

  The syntheses and SAR studies of various quinazolinone compounds are described for the dual inhibition of Pgp and MRP1 in multidrug resistance. (C) 2002 Elsevier Science Ltd. All rights reserved.