1-(2-oxo-2-phenyl-ethyl)-1H-[1,2,3]triazole-4-carboxylic acid hydroxyamide | 1092115-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-oxo-2-phenyl-ethyl)-1H-[1,2,3]triazole-4-carboxylic acid hydroxyamide
• 英文别名: NSC746458；N-hydroxy-1-phenacyltriazole-4-carboxamide
• CAS: 1092115-66-6
• 化学式: C₁₁H₁₀N₄O₃
• 分子量: 246.225
• InChiKey: AXEBXKBEJISFEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-oxo-2-phenyl-ethyl)-1H-[1,2,3]triazole-4-carboxylic acid (4-methoxy-benzyloxy)-amide 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到1-(2-oxo-2-phenyl-ethyl)-1H-[1,2,3]triazole-4-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Histone Deacetylase Inhibitors through Click Chemistry

  摘要：

  Histone deacetylase inhibitors (HDACi) are a relatively new class of chemotherapy agents. Herein, we report a click-chemistry based approach to the synthesis of HDACi. Fourteen agents were synthesized from the combination of two alkyne and seven azido precursors. The inhibition of HDAC1 and HDAC8 was then determined by in vitro enzymatic assays, after which the cytotoxicity was evaluated in the NCI human cancer cell line screen. A lead compound 5g (NSC746457) was discovered that inhibited HDAC1 at an IC50 value of 104 +/- 30 nM and proved quite potent in the cancer cell line screen with GI(50) values ranging from 3.92 mu M to 10 nM. Thus, this click HDACi design has provided a new chemical scaffold that has not only revealed a lead compound, but one which is easily amendable to further structural modifications given the modular nature of this approach.

  DOI：

  10.1021/jm8005355

文献信息

• Histone Deacetylase Inhibitors through Click Chemistry
  作者：Jie Shen、Robert Woodward、James Patrick Kedenburg、Xianwei Liu、Min Chen、Lanyan Fang、Duxin Sun、Peng George Wang

  DOI：10.1021/jm8005355

  日期：2008.12.11

  Histone deacetylase inhibitors (HDACi) are a relatively new class of chemotherapy agents. Herein, we report a click-chemistry based approach to the synthesis of HDACi. Fourteen agents were synthesized from the combination of two alkyne and seven azido precursors. The inhibition of HDAC1 and HDAC8 was then determined by in vitro enzymatic assays, after which the cytotoxicity was evaluated in the NCI human cancer cell line screen. A lead compound 5g (NSC746457) was discovered that inhibited HDAC1 at an IC50 value of 104 +/- 30 nM and proved quite potent in the cancer cell line screen with GI(50) values ranging from 3.92 mu M to 10 nM. Thus, this click HDACi design has provided a new chemical scaffold that has not only revealed a lead compound, but one which is easily amendable to further structural modifications given the modular nature of this approach.