5-amino-4-cyano-2-(4-fluorophenyl)-1,3-oxazole | 958633-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-4-cyano-2-(4-fluorophenyl)-1,3-oxazole
• 英文别名: 5-amino-2-(4-fluorophenyl)oxazole-4-carbonitrile；5-Amino-2-(4-fluorophenyl)-1,3-oxazole-4-carbonitrile；5-amino-2-(4-fluorophenyl)-1,3-oxazole-4-carbonitrile
• CAS: 958633-52-8
• 化学式: C₁₀H₆FN₃O
• 分子量: 203.176
• InChiKey: MJRPNHNJLITZBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 5-amino-4-cyano-2-(4-fluorophenyl)-1,3-oxazole 在 sodium methylate 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 2-(4-Fluorophenyl)-5-(methylamino)-1,3-oxazole-4-carbonitrile
  参考文献：
  名称：

  Potent and Selective Inhibitors of Human Reticulocyte 12/15-Lipoxygenase as Anti-Stroke Therapies

  摘要：

  A key challenge facing drug discovery today is variability of the drug target between species, such as with 12/15-lipoxygenase (12/15-LOX), which contributes to ischemic brain injury, but its human and rodent isozymes have different inhibitor specificities. In the current work, we have utilized a quantitative high-throughput (qHTS) screen to identify compound 1 (ML351), a novel chemotype for 12/15-LOX inhibition that has nanomolar potency (IC50 = 200 nM) against human 12/15-LOX and is protective against oxidative glutamate toxicity in mouse neuronal HT22 cells. In addition, it exhibited greater than 250-fold selectivity versus related LOX isozymes, was a mixed inhibitor, and did not reduce the active-site ferric ion. Lastly, 1 significantly reduced infarct size following permanent focal ischemia in a mouse model of ischemic stroke. As such, this represents the first report of a selective inhibitor of human 12/15-LOX with demonstrated in vivo activity in proof-of-concept mouse models of stroke.

  DOI：

  10.1021/jm401915r
• 作为产物：
  描述：

  对氟苯甲酰氯 、 对苯二磺酸氨基丙二酰丁氰 以 N-甲基吡咯烷酮 为溶剂， 以96%的产率得到5-amino-4-cyano-2-(4-fluorophenyl)-1,3-oxazole
  参考文献：
  名称：

  Microwave-mediated synthesis and manipulation of a 2-substituted-5-aminooxazole-4-carbonitrile library

  摘要：

  A 2-substituted-5-aminooxazole-4-carbonitrile library has been synthesised and modified via microwave-mediated and flow chemistries. One synthesised compound, 5-(1H-pyrrol-1-yl)-4-(1H-tetrazol-5-yl)-2-(thien-2-yl)oxazole, contains three distinct heterocycles attached to the central oxazole core, highlighting the structural diversity of this approach. Three oxazoles had micromolar k(i) values against cannabinoid (CB1/CB2) receptors. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.081

文献信息

• Synthesis and friedländer reactions of 5-amino-4-cyano-1,3-oxazoles
  作者：M CARREIRAS、A ELEUTERIO、C DIAS、M BRITO、D BRITES、J MARCOCONTELLES、E GOMEZSANCHEZ

  DOI：10.1016/s0385-5414(07)81101-4

  日期：2007.10.1

  The synthesis of 2-substituted 5-amino-4-cyano-1,3-oxazoles (1-4, 611) and the Friedlander-type reaction of compounds 1, 3, 4 is described. Compounds 13-17 are tacrine (18) analogues provided by the Friedlander reaction. The anti-cholinesterase activity of compounds 13, 14, 16 and 17 has been investigated.