3-(4-Methyl-pent-3-enoylamino)-pyridine-2-carboxylic acid thiazol-2-ylamide | 569688-01-3

• 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: 3-(4-Methyl-pent-3-enoylamino)-pyridine-2-carboxylic acid thiazol-2-ylamide
• 英文别名: 3-(4-methylpent-3-enoylamino)-N-(1,3-thiazol-2-yl)pyridine-2-carboxamide
• CAS: 569688-01-3
• 化学式: C₁₅H₁₆N₄O₂S
• 分子量: 316.384
• InChiKey: QLSMZADEWAIARS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Methyl-pent-3-enoylamino)-pyridine-2-carboxylic acid thiazol-2-ylamide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成 3-[2-(3,3-Dimethyl-oxiranyl)-acetylamino]-pyridine-2-carboxylic acid thiazol-2-ylamide
  参考文献：
  名称：

  Inhibitors of type I MetAPs containing pyridine-2-carboxylic acid thiazol-2-ylamide. Part 2: SAR studies on the pyridine ring 3-substituent

  摘要：

  Systematic SAR studies on the pyridine ring 3-substituent of PCAT, an inhibitor of EcMetAP1 and ScMetAP1, revealed that 3-substituents have different selectivity for EcMetAP1 and ScMetAP1. The selective inhibitors of type I MetAP are useful tools for investigating the detailed interactions between the enzymes and their inhibitors. In addition, 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.

  DOI：

  10.1016/j.bmcl.2004.11.035
• 作为产物：
  描述：

  3-氨基吡啶-2-羧酸 在 吡啶 、 三甲基乙酰氯 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.25h， 生成 3-(4-Methyl-pent-3-enoylamino)-pyridine-2-carboxylic acid thiazol-2-ylamide
  参考文献：
  名称：

  Discovery and Structural Modification of Inhibitors of Methionine Aminopeptidases from Escherichia coli and Saccharomyces cerevisiae

  摘要：

  A series of pyridine-2-carboxylic acid derivatives were synthesized according to the leads from the screening, and potent inhibitors have been obtained by structural modification. They have shown submicromolar inhibition of the enzymes (for example, for 9n, IC50 = 130 nM for EcMetAP1 and IC50 = 380 nM for ScMetAP1). They represent small-molecule MetAP inhibitors with novel structures different from alkylating fumagillin derivatives and peptidic bestatin-based MetAP inhibitor.

  DOI：

  10.1021/jm0300532