methyl 2-(4-azidobutanamido)-3-(1H-indol-3-yl)propanoate | 910581-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(4-azidobutanamido)-3-(1H-indol-3-yl)propanoate
• 英文别名: methyl (2S)-2-(4-azidobutanoylamino)-3-(1H-indol-3-yl)propanoate
• CAS: 910581-54-3
• 化学式: C₁₆H₁₉N₅O₃
• 分子量: 329.359
• InChiKey: PMOQRTHAIYKDGZ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-hydroxy-2-isopropyl-N¹-(prop-2-ynyl)succinamide 、 methyl 2-(4-azidobutanamido)-3-(1H-indol-3-yl)propanoate 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 生成 methyl (2S)-2-[4-[4-[[[4-(hydroxyamino)-4-oxo-2-propan-2-ylbutanoyl]amino]methyl]triazol-1-yl]butanoylamino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Rapid Assembly of Matrix Metalloprotease Inhibitors Using Click Chemistry

  摘要：

  A panel of 96 metalloprotease inhibitors was assembled using "click chemistry" by reacting eight zinc-binding hydroxamate warheads with 12 azide building blocks. Screens of the bidentate compounds against representative metalloproteases provided discerning inhibition fingerprints, revealing compounds with low micromolar potency against MMP-7. The relative ease and convenience of the strategy in constructing focused chemical libraries for rapid in situ screening of MMPs is thereby demonstrated.

  DOI：

  10.1021/ol061431a
• 作为产物：
  描述：

  L-色氨酸甲酯 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(4-azidobutanamido)-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Rapid Assembly of Matrix Metalloprotease Inhibitors Using Click Chemistry

  摘要：

  A panel of 96 metalloprotease inhibitors was assembled using "click chemistry" by reacting eight zinc-binding hydroxamate warheads with 12 azide building blocks. Screens of the bidentate compounds against representative metalloproteases provided discerning inhibition fingerprints, revealing compounds with low micromolar potency against MMP-7. The relative ease and convenience of the strategy in constructing focused chemical libraries for rapid in situ screening of MMPs is thereby demonstrated.

  DOI：

  10.1021/ol061431a

文献信息

• Rapid Assembly of Matrix Metalloprotease Inhibitors Using Click Chemistry
  作者：Jun Wang、Mahesh Uttamchandani、Junqi Li、Mingyu Hu、Shao Q. Yao

  DOI：10.1021/ol061431a

  日期：2006.8.1

  A panel of 96 metalloprotease inhibitors was assembled using "click chemistry" by reacting eight zinc-binding hydroxamate warheads with 12 azide building blocks. Screens of the bidentate compounds against representative metalloproteases provided discerning inhibition fingerprints, revealing compounds with low micromolar potency against MMP-7. The relative ease and convenience of the strategy in constructing focused chemical libraries for rapid in situ screening of MMPs is thereby demonstrated.