2-氨基噁唑-5-羧酸 | 881637-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氨基噁唑-5-羧酸
• 中文别名: 2-氨基恶唑-5-羧酸
• 英文名称: 2-aminooxazole-5-carboxylic acid
• 英文别名: 2-amino-1,3-oxazole-5-carboxylic acid
• CAS: 881637-11-2
• 化学式: C₄H₄N₂O₃
• mdl: MFCD11504937
• 分子量: 128.087
• InChiKey: VHGLIMPSBPUNSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

SDS

2-氨基噁唑-5-羧酸MSDS英文版

反应信息

• 作为反应物：
  描述：

  2-氨基噁唑-5-羧酸 、 二正丁胺 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以38%的产率得到2-amino-N,N-dibutyloxazole-5-carboxamide
  参考文献：
  名称：

  Discovery of the first inhibitors of bacterial enzyme d-aspartate ligase from Enterococcus faecium (Aslfm)

  摘要：

  The D-aspartate ligase of Enterococcus faecium (Asl(fm)) is an attractive target for the development of narrow-spectrum antibacterial agents that are active against multidrug-resistant E. faecium. Although there is currently little available information regarding the structural characteristics of Asl(fm), we exploited the knowledge that this enzyme belongs to the ATP-grasp superfamily to target its ATP binding site. In the first design stage, we synthesized and screened a small library of known ATP-competitive inhibitors of ATP-grasp enzymes. A series of amino-oxazoles derived from bacterial biotin carboxylase inhibitors showed low micromolar activity. The most potent inhibitor compound 12, inhibits Asl(fm) with a K-i value of 2.9 mu M. In the second design stage, a validated ligand-based pharmacophore modeling approach was used, taking the newly available inhibition data of an initial series of compounds into account. Experimental evaluation of the virtual screening hits identified two novel structural types of Asl(fm) inhibitors with 7-amino-9H-purine (18) and 7-amino-1H-pyrazolo[3,4-d]pyrimidine (30 and 34) scaffolds, and also with K-i values in the low micromolar range. Investigation the inhibitors modes of action confirmed that these compounds are competitive with respect to the ATP molecule. The binding of inhibitors to the target enzyme was also studied using isothermal titration calorimetry (ITC). Compounds 6, 12, 18, 30 and 34 represent the first inhibitors of Asl(fm) reported to date, and are an important step forward in combating infections due to E. faecium. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.017
• 作为产物：
  描述：

  2-氨基噁唑-5-羧酸乙酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以93%的产率得到2-氨基噁唑-5-羧酸
  参考文献：
  名称：

  Discovery of the first inhibitors of bacterial enzyme d-aspartate ligase from Enterococcus faecium (Aslfm)

  摘要：

  The D-aspartate ligase of Enterococcus faecium (Asl(fm)) is an attractive target for the development of narrow-spectrum antibacterial agents that are active against multidrug-resistant E. faecium. Although there is currently little available information regarding the structural characteristics of Asl(fm), we exploited the knowledge that this enzyme belongs to the ATP-grasp superfamily to target its ATP binding site. In the first design stage, we synthesized and screened a small library of known ATP-competitive inhibitors of ATP-grasp enzymes. A series of amino-oxazoles derived from bacterial biotin carboxylase inhibitors showed low micromolar activity. The most potent inhibitor compound 12, inhibits Asl(fm) with a K-i value of 2.9 mu M. In the second design stage, a validated ligand-based pharmacophore modeling approach was used, taking the newly available inhibition data of an initial series of compounds into account. Experimental evaluation of the virtual screening hits identified two novel structural types of Asl(fm) inhibitors with 7-amino-9H-purine (18) and 7-amino-1H-pyrazolo[3,4-d]pyrimidine (30 and 34) scaffolds, and also with K-i values in the low micromolar range. Investigation the inhibitors modes of action confirmed that these compounds are competitive with respect to the ATP molecule. The binding of inhibitors to the target enzyme was also studied using isothermal titration calorimetry (ITC). Compounds 6, 12, 18, 30 and 34 represent the first inhibitors of Asl(fm) reported to date, and are an important step forward in combating infections due to E. faecium. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.017

文献信息

• NOVEL COMPOUNDS
  申请人：HALSALL Christopher Thomas

  公开号：US20080009482A1

  公开（公告）日：2008-01-10

  There is provided a compound of formula (I): processes for the manufacture thereof, pharmaceutical compositions thereof and uses in therapy.

  提供了一个公式(I)的化合物，其制造过程，制药组合物及其在治疗中的用途。
• ARYLAMIDE DERIVATIVES AS TTX-S BLOCKERS
  申请人：Yamagishi Tatsuya

  公开号：US20140336377A1

  公开（公告）日：2014-11-13

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及一种芳基酰胺衍生物，其具有阻断电压门控钠通道（如TTX-S通道）的活性，并且在涉及电压门控钠通道的疾病和疾病的治疗或预防中有用。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在涉及电压门控钠通道的这种疾病的预防或治疗中的使用。
• Arylamide derivatives as TTX-S blockers
  申请人：Yamagishi Tatsuya

  公开号：US09302991B2

  公开（公告）日：2016-04-05

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及芳基酰胺衍生物，其具有阻断电压门控钠通道（TTX-S通道）的活性，并且在治疗或预防涉及电压门控钠通道的疾病和疾病方面有用。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗涉及电压门控钠通道的疾病方面使用这些化合物和组合物。
• Compounds
  申请人：AstraZeneca AB

  公开号：US07709471B2

  公开（公告）日：2010-05-04

  There is provided a compound of formula (I): processes for the manufacture thereof, pharmaceutical compositions thereof and uses in therapy.

  提供了一个公式（I）的化合物：其制造过程，制药组合物及其在治疗中的用途。
• Design, Synthesis, and Antibacterial Properties of Dual-Ligand Inhibitors of Acetyl-CoA Carboxylase
  作者：Molly A. Silvers、Gregory T. Robertson、Carol M. Taylor、Grover L. Waldrop

  DOI：10.1021/jm501082n

  日期：2014.11.13

  There is an urgent demand for the development of new antibiotics due to the increase in drug-resistant pathogenic bacteria. A novel target is the multifunctional enzyme acetyl-CoA carboxylase (ACC), which catalyzes the first committed step in fatty acid synthesis and consists of two enzymes: biotin carboxylase and carboxyltransferase. Covalently attaching known inhibitors against these enzymes with saturated hydrocarbon linkers of different lengths generated dual-ligand inhibitors. Kinetic results revealed that the dual-ligands inhibited the ACC complex in the nanomolar range. Microbiology assays showed that the dual-ligand with a 15-carbon linker did not exhibit any antibacterial activity, while the dual-ligand with a 7-carbon linker displayed broad-spectrum antibacterial activity as well as a decreased susceptibility in the development of bacterial resistance. These results suggest that the properties of the linker are vital for antibacterial activity and show how inhibiting two different enzymes with the same compound increases the overall potency while also impeding the development of resistance.