3-Amino-pyridine-2-carboxylic acid thiazol-2-ylamide | 569687-84-9

• 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-Amino-pyridine-2-carboxylic acid thiazol-2-ylamide
• 英文别名: 3-amino-N-(1,3-thiazol-2-yl)pyridine-2-carboxamide
• CAS: 569687-84-9
• 化学式: C₉H₈N₄OS
• 分子量: 220.255
• InChiKey: JPLQEHQVVPDPHY-UHFFFAOYSA-N

物化性质

• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Amino-pyridine-2-carboxylic acid thiazol-2-ylamide 、 环丁基甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙酸乙酯 为溶剂， 生成 3-(cyclobutanecarbonylamino)-N-(1,3-thiazol-2-yl)pyridine-2-carboxamide
  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-(Boc-氨基)吡啶-2-甲酸 在 1-羟基苯并三唑 、 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 为溶剂， 反应 28.0h， 生成 3-Amino-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

文献信息

• Design, synthesis and biological evaluation of substituted 3-amino-N-(thiazol-2-yl)pyrazine-2-carboxamides as inhibitors of mycobacterial methionine aminopeptidase 1
  作者：Martin Juhás、Vinod S.K. Pallabothula、Katarina Grabrijan、Martina Šimovičová、Ondřej Janďourek、Klára Konečná、Pavel Bárta、Pavla Paterová、Stanislav Gobec、Izidor Sosič、Jan Zitko

  DOI：10.1016/j.bioorg.2021.105489

  日期：2022.1

  mycobacterial methionine aminopeptidase 1 (MtMetAP1). The inhibitory activities of the presented compounds were evaluated against the MtMetAP1a isoform, and all derivatives were tested against a broad spectrum of myco(bacteria) and fungi. The cytotoxicity of the compounds was also investigated using Hep G2 cell lines. Overall, high inhibition of the isolated enzyme was observed for 3-substituted N-(thiazo

  由结核分枝杆菌(Mtb)引起的结核病 (TB)是世界范围内由单一传染性病原体引起的第一大死亡原因。结核病的治疗是漫长的，而且常常因耐药性的增加而复杂化。因此需要具有新作用机制的新化合物。我们介绍了基于吡嗪的主要抗分枝杆菌药物靶标 - 分枝杆菌蛋氨酸氨基肽酶 1 (MtMetAP1) 抑制剂的设计、合成和生物学评价。针对 MtMetAP1a 异构体评估了所提出化合物的抑制活性，并针对广谱的分枝杆菌（细菌）和真菌测试了所有衍生物。还使用 Hep G2 细胞系研究了化合物的细胞毒性。 总体而言，对于 3-取代的N- (thiazol-2-yl)pyrazine-2-carboxamides，观察到对分离酶的高度抑制，特别是当取代基由 2-取代的苯甲酰胺表示时。抑制程度强烈依赖于使用的金属辅因子。在Ni 2+存在下观察到最高的抑制作用。几种化合物在体外对 Mtb（Mtb H37Ra 和 H37Rv）的效力也表现平平。尽管细菌和真菌
• Discovery and Structural Modification of Inhibitors of Methionine Aminopeptidases from <i>Escherichia </i><i>c</i><i>oli </i>and <i>Saccharomyces </i><i>c</i><i>erevisiae</i>
  作者：Qun-Li Luo、Jing-Ya Li、Zhi-Ying Liu、Ling-Ling Chen、Jia Li、Zhen Qian、Qiang Shen、Yu Li、Gerald H. Lushington、Qi-Zhuang Ye、Fa-Jun Nan

  DOI：10.1021/jm0300532

  日期：2003.6.1

  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.
• Inhibitors of type I MetAPs containing pyridine-2-carboxylic acid thiazol-2-ylamide. Part 2: SAR studies on the pyridine ring 3-substituent
  作者：Qun-Li Luo、Jing-Ya Li、Ling-Ling Chen、Jia Li、Qi-Zhuang Ye、Fa-Jun Nan

  DOI：10.1016/j.bmcl.2004.11.035

  日期：2005.2

  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.