ethyl 1-[(2-hydroxyphenyl)methyl]-5-methyl-1H-pyrazole-3-carboxylate | 851205-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-[(2-hydroxyphenyl)methyl]-5-methyl-1H-pyrazole-3-carboxylate
• 英文别名: Ethyl 1-[(2-hydroxyphenyl)methyl]-5-methylpyrazole-3-carboxylate
• CAS: 851205-66-8
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: JINDVXOAXSOJBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-[(2-hydroxyphenyl)methyl]-5-methyl-1H-pyrazole-3-carboxylate 在 lithium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-[(2-{[(2,4-dichlorophenyl)methyl]oxy}phenyl)methyl]-5-methyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Identification of novel pyrazole acid antagonists for the EP1 receptor

  摘要：

  The discovery, synthesis and structure-activity relationship (SAR) of a novel series of EP1 receptor antagonists is described. Pyrazole acid 4, identified from a chemical array, had desirable physicochemical properties, an excellent in vitro microsomal inhibition and cytochrome P450 (CYP450) profile and good exposure levels in blood. This compound had an ED50 of 1.3 mg/kg in a rat pain model. A range of more potent analogues in the in vitro assay was identified using efficient array chemistry. These EP1 antagonists have potential as agents in the treatment of PGE(2) mediated pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.086
• 作为产物：
  描述：

  tert-butyl N-[(2-hydroxyphenyl)methylideneamino]carbamate 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl 1-[(2-hydroxyphenyl)methyl]-5-methyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Identification of novel pyrazole acid antagonists for the EP1 receptor

  摘要：

  The discovery, synthesis and structure-activity relationship (SAR) of a novel series of EP1 receptor antagonists is described. Pyrazole acid 4, identified from a chemical array, had desirable physicochemical properties, an excellent in vitro microsomal inhibition and cytochrome P450 (CYP450) profile and good exposure levels in blood. This compound had an ED50 of 1.3 mg/kg in a rat pain model. A range of more potent analogues in the in vitro assay was identified using efficient array chemistry. These EP1 antagonists have potential as agents in the treatment of PGE(2) mediated pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.086

文献信息

• Heterocyclyl compounds
  申请人：Giblin Martin Paul Gerard

  公开号：US20070060596A1

  公开（公告）日：2007-03-15

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein W, X, Y, Z, R 1 , R 2a , R 2b , and R x , R 8 and R 9 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  式(I)或其药学上可接受的衍生物的化合物： 其中W、X、Y、Z、R1、R2a、R2b和Rx、R8和R9如规范中所定义，制备这种化合物的过程，包括这种化合物的制药组合物以及这种化合物在医学上的应用。
• HETEROCYCLYL COMPOUNDS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1675832B1

  公开（公告）日：2008-02-20
• Identification of novel pyrazole acid antagonists for the EP1 receptor
  作者：Stephen C. McKeown、Adrian Hall、Gerard M.P. Giblin、Olivier Lorthioir、Richard Blunt、Xiao Q. Lewell、Richard J. Wilson、Susan H. Brown、Anita Chowdhury、Tanya Coleman、Stephen P. Watson、Iain P. Chessell、Adrian Pipe、Nick Clayton、Paul Goldsmith

  DOI：10.1016/j.bmcl.2006.06.086

  日期：2006.9

  The discovery, synthesis and structure-activity relationship (SAR) of a novel series of EP1 receptor antagonists is described. Pyrazole acid 4, identified from a chemical array, had desirable physicochemical properties, an excellent in vitro microsomal inhibition and cytochrome P450 (CYP450) profile and good exposure levels in blood. This compound had an ED50 of 1.3 mg/kg in a rat pain model. A range of more potent analogues in the in vitro assay was identified using efficient array chemistry. These EP1 antagonists have potential as agents in the treatment of PGE(2) mediated pain. (c) 2006 Elsevier Ltd. All rights reserved.