6-hydroxy-2-trifluoromethyl-3H-quinazolin-4-one | 35982-14-0

• 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: 6-hydroxy-2-trifluoromethyl-3H-quinazolin-4-one
• 英文别名: 2-Trifluoromethyl-quinazoline-4,6-diol；6-hydroxy-2-(trifluoromethyl)-3H-quinazolin-4-one
• CAS: 35982-14-0
• 化学式: C₉H₅F₃N₂O₂
• 分子量: 230.146
• InChiKey: XZPZSUSGMFXBEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  334.6±52.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2-trifluoromethyl-3H-quinazolin-4-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 4-tert-Butylamino-2-trifluoromethyl-quinazolin-6-ol
  参考文献：
  名称：

  Quinazolines as cyclin dependent kinase inhibitors

  摘要：

  Quinazolines have been identified as inhibitors of CDK4/D1 and CDK2/E. Aspects of the SAR were investigated using solution-phase, parallel synthesis. An X-ray crystal structure was obtained of quinazoline 51 bound in CDK2 and key interactions within the ATP binding pocket are defined.

  DOI：

  10.1016/s0960-894x(01)00185-8
• 作为产物：
  描述：

  2-氨基-5-羟基苯甲酸 在 ammonium acetate 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 6-hydroxy-2-trifluoromethyl-3H-quinazolin-4-one
  参考文献：
  名称：

  The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies

  摘要：

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.047

文献信息

• Quinazolines as cyclin dependent kinase inhibitors
  作者：Thais M. Sielecki、Tricia L. Johnson、Jie Liu、Jodi K. Muckelbauer、Robert H. Grafstrom、Sarah Cox、John Boylan、Catherine R. Burton、Haiying Chen、Angela Smallwood、Chong-Hwan Chang、Michael Boisclair、Pamela A. Benfield、George L. Trainor、Steven P. Seitz

  DOI：10.1016/s0960-894x(01)00185-8

  日期：2001.5

  Quinazolines have been identified as inhibitors of CDK4/D1 and CDK2/E. Aspects of the SAR were investigated using solution-phase, parallel synthesis. An X-ray crystal structure was obtained of quinazoline 51 bound in CDK2 and key interactions within the ATP binding pocket are defined.
• The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of In vitro and In vivo studies
  作者：Moorthy S.S. Palanki、Paul E. Erdman、Minghuan Ren、Mark Suto、Brydon L. Bennett、Anthony Manning、Lynn Ransone、Cheryl Spooner、Sonal Desai、Arnie Ow、Ryuichi Totsuka、Peter Tsao、Wataru Toriumi

  DOI：10.1016/j.bmcl.2003.08.047

  日期：2003.11

  We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3-pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described. (C) 2003 Elsevier Ltd. All rights reserved.