5-azido-2-hydroxy-N-propylbenzamide | 1290070-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-azido-2-hydroxy-N-propylbenzamide
• CAS: 1290070-70-0
• 化学式: C₁₀H₁₂N₄O₂
• 分子量: 220.231
• InChiKey: CUYPDKAMYUSXCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azido-2-hydroxy-N-propylbenzamide 、 4-戊基苯乙炔 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以66%的产率得到2-hydroxy-5-[4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl]-N-propyl-benzamide
  参考文献：
  名称：

  Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production

  摘要：

  A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues, 29g showed a significant inhibitory activity (IC50 = 12.8 mu M). The inhibitory effects of 29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.034
• 作为产物：
  描述：

  5-氨基水杨酸 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 20.34h， 生成 5-azido-2-hydroxy-N-propylbenzamide
  参考文献：
  名称：

  Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production

  摘要：

  A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues, 29g showed a significant inhibitory activity (IC50 = 12.8 mu M). The inhibitory effects of 29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.034

文献信息

• Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production
  作者：Jieun Yoon、Lan Cho、Sang Kook Lee、Jae-Sang Ryu

  DOI：10.1016/j.bmcl.2011.02.034

  日期：2011.4

  A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues, 29g showed a significant inhibitory activity (IC50 = 12.8 mu M). The inhibitory effects of 29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression. (C) 2011 Elsevier Ltd. All rights reserved.