pyridine-2-carboxylic acid (5-methyl-isoxazol-3-yl)-amide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridine-2-carboxylic acid (5-methyl-isoxazol-3-yl)-amide
• 英文别名: N-(5-methyl-1,2-oxazol-3-yl)pyridine-2-carboxamide
• 化学式: C₁₀H₉N₃O₂
• mdl: MFCD15109466
• 分子量: 203.2
• InChiKey: KAOZPFRUKSOJGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基-5-甲基异恶唑 、 2-吡啶甲酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以69%的产率得到pyridine-2-carboxylic acid (5-methyl-isoxazol-3-yl)-amide
  参考文献：
  名称：

  Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors

  摘要：

  Inhibitors of methionine aminopeptidases (MetAPs) are treatment options for various pathological conditions. Several inhibitor classes have been described previously, but only few data on the subtype selectivity, which is of crucial importance for these enzymes, is available. We present a systematic study on the subtype- and species-selectivity of MetAP inhibitors that require the binding of an auxiliary metal ion. This includes, in particular, compounds based on the benzimidazole pharmacophore, but also hydroxyquinoline and picolinic acid derivatives. Our data indicates that a significant degree of selectivity can be attained with metal-dependent MetAP inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.093

文献信息

• Inhibitors of type I MetAPs containing pyridine-2-carboxylic acid thiazol-2-ylamide. Part 1: SAR studies on the determination of the key scaffold
  作者：Qun-Li Luo、Jing-Ya Li、Zhi-Ying Liu、Ling-Ling Chen、Jia Li、Qi-Zhuang Ye、Fa-Jun Nan

  DOI：10.1016/j.bmcl.2004.11.034

  日期：2005.2

  Systematic SAR studies on the HTS hit pyridine-2-carboxylic acid thiazol-2-ylamide (PACT) analogues revealed that the scaffold of OCAT is indispensable for the inhibition of type I MetAP. For effective inhibition of the enzyme, the most suitable position to modify is the 3-position of the pyridine ring of PCAT, and the best substituents are those containing O or N atoms connected directly with the pyridine ring. These findings provide useful information for the design and discovery of more potent inhibitors of type I MetAPs. (C) 2004 Elsevier Ltd. All rights reserved.
• Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors
  作者：Markus A. Altmeyer、Aline Marschner、Rolf Schiffmann、Christian D. Klein

  DOI：10.1016/j.bmcl.2010.05.093

  日期：2010.7

  Inhibitors of methionine aminopeptidases (MetAPs) are treatment options for various pathological conditions. Several inhibitor classes have been described previously, but only few data on the subtype selectivity, which is of crucial importance for these enzymes, is available. We present a systematic study on the subtype- and species-selectivity of MetAP inhibitors that require the binding of an auxiliary metal ion. This includes, in particular, compounds based on the benzimidazole pharmacophore, but also hydroxyquinoline and picolinic acid derivatives. Our data indicates that a significant degree of selectivity can be attained with metal-dependent MetAP inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.