4-(4-Isopropylphenyl)-1h-pyrazol-3-amine | 941573-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-Isopropylphenyl)-1h-pyrazol-3-amine
• 英文别名: 4-(4-propan-2-ylphenyl)-1H-pyrazol-5-amine
• CAS: 941573-49-5
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: YMPIKHBVZDWEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-Isopropylphenyl)-1h-pyrazol-3-amine 在 5%-palladium/activated carbon 、 氢气 、 sodium acetate 、 N,N-二甲基苯胺 、 lithium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 23.0h， 生成 3-(4-isopropylphenyl)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid
  参考文献：
  名称：

  Novel 3,6,7-Substituted Pyrazolopyrimidines as Positive Allosteric Modulators for the Hydroxycarboxylic Acid Receptor 2 (GPR109A)

  摘要：

  A number of pyrazolopyrimidines were synthesized and tested for their positive allosteric modulation of the HCA(2) receptor (GPR109A). Compound 24, an efficacious and potent agonist and allosteric enhancer of nicotinic acid's action, was the basis for most other compounds. Interestingly, some of the compounds were found to increase the efficacy of the endogenous ligand 3-hydroxybutyrate and enhance its potency almost 10-fold. This suggests that the pyrazolopyrimidines may have therapeutic value when given alone.

  DOI：

  10.1021/jm300164q
• 作为产物：
  描述：

  4-异丙基苯乙腈 在 盐酸肼 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 18.0h， 生成 4-(4-Isopropylphenyl)-1h-pyrazol-3-amine
  参考文献：
  名称：

  Novel tricyclic pyrazolopyrimidines as potent and selective GPR119 agonists

  摘要：

  Systematic SAR optimization of the GPR119 agonist lead 1, derived from an internal HTS campaign, led to compound 29. Compound 29 displays significantly improved in vitro activity and oral exposure, leading to GLP1 elevation in acutely dosed mice and reduced glucose excursion in an OGTT study in rats at doses >= 10 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.010

文献信息

• Discovery of pyrazolopyrimidines as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A
  作者：Hong C. Shen、Andrew K.P. Taggart、Larissa C. Wilsie、M. Gerard Waters、Milton L. Hammond、James R. Tata、Steven L. Colletti

  DOI：10.1016/j.bmcl.2008.08.039

  日期：2008.9

  Pyrazolopyrimidines were discovered as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A. In addition to its intrinsic activity, compound 9n significantly enhances nicotinic acid binding to the receptor, thereby potentiating the functional efficacy of nicotinic acid.

  发现吡唑并嘧啶是高亲和力烟酸受体GPR109A的第一类变构激动剂。除了其固有活性外，化合物9n还显着增强了烟酸与受体的结合，从而增强了烟酸的功能功效。
• RHO-ASSOCIATED PROTEIN KINASE INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING SAME, AND PREPARATION METHOD AND USE THEREOF
  申请人：BEIJING TIDE PHARMACEUTICAL CO., LTD.

  公开号：US20190276440A1

  公开（公告）日：2019-09-12

  The present invention relates to a Rho-associated protein kinase inhibitor of formula (I), a pharmaceutical composition comprising the same, a preparation method thereof, and a use of the same in preventing or treating a disease mediated by Rho-associated protein kinase (ROCK).
• Novel tricyclic pyrazolopyrimidines as potent and selective GPR119 agonists
  作者：Mihai Azimioara、Phil Alper、Christopher Cow、Daniel Mutnick、Victor Nikulin、Gerald Lelais、John Mecom、Matthew McNeill、Pierre-Yves Michellys、Zhiliang Wang、Esther Reding、Michael Paliotti、Jing Li、Dingjiu Bao、Jocelyn Zoll、Young Kim、Matthew Zimmerman、Todd Groessl、Tove Tuntland、Sean B. Joseph、Peter McNamara、H. Martin Seidel、Robert Epple

  DOI：10.1016/j.bmcl.2014.10.010

  日期：2014.12

  Systematic SAR optimization of the GPR119 agonist lead 1, derived from an internal HTS campaign, led to compound 29. Compound 29 displays significantly improved in vitro activity and oral exposure, leading to GLP1 elevation in acutely dosed mice and reduced glucose excursion in an OGTT study in rats at doses >= 10 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.
• Novel 3,6,7-Substituted Pyrazolopyrimidines as Positive Allosteric Modulators for the Hydroxycarboxylic Acid Receptor 2 (GPR109A)
  作者：Clara C. Blad、Jacobus P. D. van Veldhoven、Corné Klopman、Dieter R. Wolfram、Johannes Brussee、J. Robert Lane、Adriaan P. IJzerman

  DOI：10.1021/jm300164q

  日期：2012.4.12

  A number of pyrazolopyrimidines were synthesized and tested for their positive allosteric modulation of the HCA(2) receptor (GPR109A). Compound 24, an efficacious and potent agonist and allosteric enhancer of nicotinic acid's action, was the basis for most other compounds. Interestingly, some of the compounds were found to increase the efficacy of the endogenous ligand 3-hydroxybutyrate and enhance its potency almost 10-fold. This suggests that the pyrazolopyrimidines may have therapeutic value when given alone.