3-(Trifluoromethyl)isatoic anhydride | 72985-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-(Trifluoromethyl)isatoic anhydride
• 英文别名: 8-(trifluoromethyl)-1H-3,1-benzoxazine-2,4-dione
• CAS: 72985-50-3
• 化学式: C₉H₄F₃NO₃
• 分子量: 231.131
• InChiKey: FWLOMSMDWVUGDL-UHFFFAOYSA-N

物化性质

• 熔点：
  184-186 °C (decomp)
• 密度：
  1.542±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(Trifluoromethyl)isatoic anhydride 在 盐酸 、 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 N-(3,4-dichlorophenyl)-1,2-dihydro-4-hydroxy-N,1-dimethyl-2-oxo-8-(trifluoromethyl)-3-quinolinecarboxamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship

  摘要：

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

  DOI：

  10.1021/jm031044w
• 作为产物：
  描述：

  7-三氟甲基靛红 在 硫酸 、 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以81%的产率得到3-(Trifluoromethyl)isatoic anhydride
  参考文献：
  名称：

  Reissenweber, Gernot; Mangold, Dietrich, Angewandte Chemie, 1980, vol. 92, # 3, p. 196 - 197

  摘要：

  DOI：

文献信息

• Discovery of evodiamine derivatives as potent insecticide candidates
  作者：Jingbo Liu、Yabing Shi、Shuting Chen、Fengyun Li、Wen Wen、Yuanhong Wang

  DOI：10.1016/j.bmc.2022.116727

  日期：2022.5

  search for novel more effective insecticides, natural products could be used as ideal template compounds due to their good environmental compatibility, various bioactivities, unique scaffolds and mode of action. We have found that natural product evodiamine, the main active component from the fruits of Evodia rutaecarpa (Juss.) Benth, displayed obvious insecticidal activities against lepidoptera pests

  在寻找新型更有效的杀虫剂时，天然产物具有良好的环境相容性、多种生物活性、独特的支架和作用方式，可作为理想的模板化合物。我们发现吴茱萸果实的主要活性成分天然产物吴茱萸碱对鳞翅目具有明显的杀虫活性。害虫。为了继续我们的研究，我们合理设计和合成了一系列吴茱萸碱衍生物3a-3aa。杀幼虫活性结果表明，大部分目标化合物对Mythimna separata、Plutella xylostella和Helicoverpa armigera的效果优于吴茱萸碱、苦参碱和鱼藤酮，其中3z表现出优异的杀幼虫活性（2.5 mg/L对M. separata的杀幼虫活性为65%， 75% 1.0 mg/L 对P. xylostella和 85% 10 mg/L 对H. armigera，分别），远优于吴茱萸碱（0%）、苦参碱（0%）和鱼藤酮（0%）。初步构效关系表明吴茱萸碱E环上的氟原子对杀幼虫活性有正向影响。钙显像
• Achieving improved permeability by hydrogen bond donor modulation in a series of MGAT2 inhibitors
  作者：James S. Scott、David J. Berry、Hayley S. Brown、Linda Buckett、David S. Clarke、Kristin Goldberg、Julian A. Hudson、Andrew G. Leach、Philip A. MacFaul、Piotr Raubo、Graeme Robb

  DOI：10.1039/c3md00156c

  日期：——

  Monoacylglycerolacetyltransferase-2 (MGAT2) is a potential target for the treatment of type II diabetes. We report here the optimisation of a series of MGAT2 inhibitors with regard to their potency and permeability. Improvements in permeability, as measured by increased flux in a Caco-2 assay, were achieved through substitution at the 9-position of the core. We propose that reduction of the NH hydrogen-bond donor strength was primarily responsible for these effects.

  单酰甘油乙酰转移酶-2（MGAT2）是治疗2型糖尿病的潜在靶点。我们在此报告了一系列MGAT2抑制剂在有效性和通透性方面的优化。通过在核心的9位进行替代，我们在Caco-2测定中观察到通透性改善，表现为流量增加。我们认为NH氢键供体强度的降低是导致这些效果的主要原因。
• REISSENWEBER G.; MANGOLD D., ANGEW. CHEM., 1980, 92, NO 3, 196-197
  作者：REISSENWEBER G.、 MANGOLD D.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship
  作者：Stig Jönsson、Gunnar Andersson、Tomas Fex、Tomas Fristedt、Gunnar Hedlund、Karl Jansson、Lisbeth Abramo、Ingela Fritzson、Olga Pekarski、Anna Runström、Helena Sandin、Ingela Thuvesson、Anders Björk

  DOI：10.1021/jm031044w

  日期：2004.4.1

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).
• Reissenweber, Gernot; Mangold, Dietrich, Angewandte Chemie, 1980, vol. 92, # 3, p. 196 - 197
  作者：Reissenweber, Gernot、Mangold, Dietrich

  DOI：——

  日期：——