Furan-2-carboxylic acid N'-(2-amino-6-chloro-pyrimidin-4-yl)-hydrazide | 394652-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: Furan-2-carboxylic acid N'-(2-amino-6-chloro-pyrimidin-4-yl)-hydrazide
• 英文别名: N'-(2-amino-6-chloropyrimidin-4-yl)furan-2-carbohydrazide
• CAS: 394652-85-8
• 化学式: C₉H₈ClN₅O₂
• 分子量: 253.648
• InChiKey: YJLQAVVMNAYSBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Furan-2-carboxylic acid N'-(2-amino-6-chloro-pyrimidin-4-yl)-hydrazide 在 四(三苯基膦)钯 、 N,O-双三甲硅基乙酰胺 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 [3-(5-Amino-2-furan-2-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-phenyl]-methanol
  参考文献：
  名称：

  2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1

  摘要：

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.086
• 作为产物：
  描述：

  2-呋喃甲酰肼 、 2-氨基-4,6-二氯嘧啶 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 Furan-2-carboxylic acid N'-(2-amino-6-chloro-pyrimidin-4-yl)-hydrazide
  参考文献：
  名称：

  Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines

  摘要：

  Antagonism of the adenosine A(2a) receptor offers great promise in the treatment of Parkinson's disease. In the course of exploring pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A(2A) antagonists, which led to clinical candidate SCH 420814, we prepared 1,2,4-triazolo[1,5-c]pyrimidines with potent and selective (vs A(1)) A(2a) antagonist activity, including oral activity in the rat haloperidol-induced catalepsy model. Structure-activity relationships and plasma levels are described for this series. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.075

文献信息

• 2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1
  作者：Julius J. Matasi、John P. Caldwell、Hongtao Zhang、Ahmad Fawzi、Mary E. Cohen-Williams、Geoffrey B. Varty、Deen B. Tulshian

  DOI：10.1016/j.bmcl.2005.05.086

  日期：2005.8

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.
• Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines
  作者：Bernard R. Neustadt、Hong Liu、Jinsong Hao、William J. Greenlee、Andrew W. Stamford、Carolyn Foster、Leyla Arik、Jean Lachowicz、Hongtao Zhang、Rosalia Bertorelli、Silva Fredduzzi、Geoffrey Varty、Mary Cohen-Williams、Kwokei Ng

  DOI：10.1016/j.bmcl.2008.11.075

  日期：2009.2

  Antagonism of the adenosine A(2a) receptor offers great promise in the treatment of Parkinson's disease. In the course of exploring pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A(2A) antagonists, which led to clinical candidate SCH 420814, we prepared 1,2,4-triazolo[1,5-c]pyrimidines with potent and selective (vs A(1)) A(2a) antagonist activity, including oral activity in the rat haloperidol-induced catalepsy model. Structure-activity relationships and plasma levels are described for this series. (C) 2008 Elsevier Ltd. All rights reserved.