2-Amino-3-(i-propylcarbamoyl)-5-phenylpyrazine | 113424-79-6

• 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-(i-propylcarbamoyl)-5-phenylpyrazine
• 英文别名: 3-amino-N-isopropyl-6-phenylpyrazine-2-carboxamide；3-amino-6-phenyl-N-propan-2-ylpyrazine-2-carboxamide
• CAS: 113424-79-6
• 化学式: C₁₄H₁₆N₄O
• 分子量: 256.307
• InChiKey: QXWRLZKPHCMBOO-UHFFFAOYSA-N

物化性质

• 沸点：
  442.4±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Amino-3-(i-propylcarbamoyl)-5-phenylpyrazine 、 原甲酸三乙酯 反应 7.0h， 以58%的产率得到3-i-Propyl-6-phenyl-4(3H)-pteridinone
  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：
• 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-(i-propylcarbamoyl)-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

• 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：——