methyl 5-azido-2-hydroxybenzoate | 1239028-02-4

• 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: methyl 5-azido-2-hydroxybenzoate
• CAS: 1239028-02-4
• 化学式: C₈H₇N₃O₃
• 分子量: 193.162
• InChiKey: ZFOSEGXRSNXLDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.29
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 5-azido-2-hydroxybenzoate 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.5h， 生成 {2-hydroxy-5-[4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl]phenyl}-1-piperidinylmethanone
  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-氨基水杨酸甲酯 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 以60%的产率得到methyl 5-azido-2-hydroxybenzoate
  参考文献：
  名称：

  A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly

  摘要：

  Lavendustin-mimetic small molecules modifying the linker -CH(2)-NH- with an 1,2,3-triazole ring have been synthesized via a click chemistry. Two pharmacophoric fragments of lavendustin were varied to investigate chemical space and the auxophoric -CH(2)-NH- was altered to an 1,2,3-triazole for rapid click conjugation. The small molecules were evaluated against HCT116 colon cancer and CCRF-CEM leukemia cell lines. Among 28 analogues, 3-phenylpropyl ester 26b inhibited CCRF-CEM leukemia cell growth with GI(50) value of 0.9 mu M. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.014