2-Amino-3-(2-hydroxyethylcarbamoyl)-5-phenylpyrazine | 113424-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-Amino-3-(2-hydroxyethylcarbamoyl)-5-phenylpyrazine
• 英文别名: 3-amino-N-(2-hydroxyethyl)-6-phenylpyrazine-2-carboxamide；3-amino-6-phenyl-pyrazine-2-carboxylic acid (2-hydroxy-ethyl)-amide
• CAS: 113424-82-1
• 化学式: C₁₃H₁₄N₄O₂
• 分子量: 258.28
• InChiKey: WHRVKBWPJZUNCW-UHFFFAOYSA-N

物化性质

• 沸点：
  507.0±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-amino-3-ethoxycarbonyl-5-phenylpyrazine 1-oxide 在 三氯化磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 2-Amino-3-(2-hydroxyethylcarbamoyl)-5-phenylpyrazine
  参考文献：
  名称：

  Meester, J. W. G. De; Kraus, W.; Plas, H. C. van der, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1109 - 1116

  摘要：

  DOI：

文献信息

• Novel pyrazine compounds as transforming growth factor (TGF) compounds
  申请人：Pfizer Inc

  公开号：US20040180905A1

  公开（公告）日：2004-09-16

  Novel pyrazine compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor (“TGF”)-&bgr; signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer and fibrotic diseases.

  本发明描述了新型吡啶化合物，包括其衍生物，以及用于其制备的中间体，含有它们的药物组合物以及它们的药用。本发明的化合物是转化生长因子（“TGF”）-β信号通路的有效抑制剂。它们在治疗包括癌症和纤维病等各种与TGF相关的疾病状态中非常有用。
• 6-Arylpyrazine-2-carboxamides: A New Core for <i>Trypanosoma brucei</i> Inhibitors
  作者：Raphaël Rahmani、Kung Ban、Amy J. Jones、Lori Ferrins、Danny Ganame、Melissa L. Sykes、Vicky M. Avery、Karen L. White、Eileen Ryan、Marcel Kaiser、Susan A. Charman、Jonathan B. Baell

  DOI：10.1021/acs.jmedchem.5b00438

  日期：2015.9.10

  From a whole-organism high throughput screen of approximately 87000 compounds against Trypanosoma brucei brucei, we recently identified eight new unique compounds for the treatment of human African trypanosomiasis. In an effort to understand the structure activity relationships around these compounds, we report for the first time our results on a new class of trypanocides, the pyrazine carboxamides. Attracted by the low molecular weight (270 g.mol(-1)) of our starting hit (9) and its potency (0.49 mu M), the SAR around the core was explored, leading to compounds having an EC50 as low as 25 nM against T. b. brucei and being more than 1500 times less toxic against mammalian L6 and HEK293 cell lines. The most potent compounds in the series were exquisitely selective for T. brucei over a panel of other protozoan parasites, showing an excellent correlation with the human infective parasite Trypanosoma brucei rhodesiense, the most potent compound (65) having an EC50 of 24 nM. The compounds are highly drug-like and are able to penetrate the CNS, their only limitation currently being their rate of microsomal metabolism. To that effect, efforts to identify potential metabolites of selected compounds are also reported.
• DE, MEESTER J. W. G.;KRAUS, W.;VAN, DER PLAS H. C.;BRONS, H. J.;MIDDELHOV+, J. HETEROCYCL. CHEM., 24,(1987) N 4, 1109-1116
  作者：DE, MEESTER J. W. G.、KRAUS, W.、VAN, DER PLAS H. C.、BRONS, H. J.、MIDDELHOV+

  DOI：——

  日期：——
• Meester, J. W. G. De; Kraus, W.; Plas, H. C. van der, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1109 - 1116
  作者：Meester, J. W. G. De、Kraus, W.、Plas, H. C. van der、Brons, H. J.、Middelhoven, W. J.

  DOI：——

  日期：——