3-(methylthio)-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine | 1264296-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(methylthio)-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine
• 英文别名: 3-methylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-amine
• CAS: 1264296-73-2
• 化学式: C₁₁H₁₀F₃N₃S
• 分子量: 273.282
• InChiKey: IVHHTBIOAKUOTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(methylthio)-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine 在 双氧水 、 caesium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 36.0h， 生成 (S)-methyl 8-(3-fluorobenzyl)-2-(methylsulfonyl)-3-(4-(trifluoromethyl)phenyl)-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,4-e]pyrimidine-8-carboxylate
  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
• 作为产物：
  描述：

  3,3-bis(methylthio)-2-(4-(trifluoromethyl)phenyl)acrylonitrile 在 盐酸肼 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 0.5h， 生成 3-(methylthio)-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-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

• [EN] COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS POUVANT SERVIR DE MODULATEURS DE L'ACTIVITÉ DU GPR119
  申请人：IRM LLC

  公开号：WO2011014520A3

  公开（公告）日：2011-06-23
• 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.