methyl 2-hydroxy-5-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]benzoate | 1239028-25-1

• 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 2-hydroxy-5-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]benzoate
• 英文别名: Methyl 2-hydroxy-5-[4-(2-methoxyphenyl)triazol-1-yl]benzoate
• CAS: 1239028-25-1
• 化学式: C₁₇H₁₅N₃O₄
• 分子量: 325.324
• InChiKey: JACHKEXSBSILGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-5-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]benzoate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-hydroxy-5-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]benzoic acid
  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
• 作为产物：
  描述：

  2-乙炔基苯甲醚 、 methyl 5-azido-2-hydroxybenzoate 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 96.0h， 以74%的产率得到methyl 2-hydroxy-5-[4-(2-methoxyphenyl)-1H-1,2,3-triazol-1-yl]benzoate
  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

文献信息

• A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly
  作者：Jieun Yoon、Jae-Sang Ryu

  DOI：10.1016/j.bmcl.2010.05.014

  日期：2010.7

  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.