ethyl 2-methyl-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-6-carboxylate | 99056-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: ethyl 2-methyl-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 4,7-dihydro-2-methyl-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate；2-methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester；2-Methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-carbonsaeure-aethylester
• CAS: 99056-35-6
• 化学式: C₁₀H₁₁N₃O₃
• mdl: MFCD00067951
• 分子量: 221.216
• InChiKey: WXRXRSKNZBVDDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  373.6±52.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

安全信息

• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-6-carboxylate 在 水 、 溴 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.17h， 生成 C₂₃H₃₁BrN₄O₂
  参考文献：
  名称：

  Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

  摘要：

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.

  DOI：

  10.1021/jm400182t
• 作为产物：
  描述：

  3-氨基-5-甲基吡唑 、 乙氧基甲叉丙二酸二乙酯 在 溶剂黄146 作用下， 生成 ethyl 2-methyl-7-oxo-1H-pyrazolo[1,5-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  The Structure of Certain Polyazaindenes. II. The Product from Ethyl Acetoacetate and 3-Amino-1,2,4-triazole

  摘要：

  DOI：

  10.1021/jo01088a014

文献信息

• 4-Quinolone Derivatives:  High-Affinity Ligands at the Benzodiazepine Site of Brain GABA_A Receptors. Synthesis, Pharmacology, and Pharmacophore Modeling
  作者：Erik Lager、Pierre Andersson、Jakob Nilsson、Ingrid Pettersson、Elsebet Østergaard Nielsen、Mogens Nielsen、Olov Sterner、Tommy Liljefors

  DOI：10.1021/jm058057p

  日期：2006.4.1

  The 3-ethoxycarbonyl-4-quinolone compound I has previously been identified via a database search as an interesting lead compound for ligand binding at the benzodiazepine site of GABA(A) receptors (Kahnberg et al. J. Mol. Graphics Modelling 2004, 23, 253-261). Pharmacophore-guided optimization of this lead compound yielded a number of high-affinity ligands for the benzodiazepine site including compounds 20 and 23-25 displaying sub-nanomolar affinities. A few of the compounds have been tested on the alpha(1)beta(2)gamma(2s) and alpha(3)beta(2)gamma(2s) GABA(A) receptor subtypes, and two of the compounds (5 and 19) display selectivity for alpha(1) versus alpha(3)-containing receptors by a factor of 22 and 27, respectively. This selectivity for alpha(1)beta(2)gamma(2s) is in the same range as that for the well-known alpha(1) subunit selective compound zolpidem.
• The Structure of Certain Polyazaindenes. II. The Product from Ethyl Acetoacetate and 3-Amino-1,2,4-triazole
  作者：C. F. H. ALLEN、H. R. BEILFUSS、D. M. BURNESS、G. A. REYNOLDS、J. F. TINKER、J. A. VanALLAN

  DOI：10.1021/jo01088a014

  日期：1959.6
• Discovery of 7-Oxopyrazolo[1,5-<i>a</i>]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists
  作者：Mojgan Aghazadeh Tabrizi、Pier Giovanni Baraldi、Giulia Saponaro、Allan R. Moorman、Romeo Romagnoli、Delia Preti、Stefania Baraldi、Emanuela Ruggiero、Cristina Tintori、Tiziano Tuccinardi、Fabrizio Vincenzi、Pier Andrea Borea、Katia Varani

  DOI：10.1021/jm400182t

  日期：2013.6.13

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.
• 3-Halopyrazolo[1,5-a]pyrimidines as promising precursors of novel C-nucleosides
  作者：E. M. Mukhin、K. V. Savateev、E. K. Voinkov、E. N. Ulomsky、V. L. Rusinov

  DOI：10.1007/s11172-023-3965-0

  日期：2023.8