3-methyl-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine | 1264296-30-1

• 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-methyl-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine
• 英文别名: 3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-amine；5-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-amine
• CAS: 1264296-30-1；1221133-66-9
• 化学式: C₁₁H₁₀F₃N₃
• 分子量: 241.216
• InChiKey: QSCFARQGPFPLJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三氟乙酸 、 sodium iodide 作用下， 以 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 ethyl 3-(3-fluorophenyl)-2-(2-(formyloxymethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-yl)-2-methylpropanoate
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY
  [FR] COMPOSÉS ET COMPOSITIONS POUVANT SERVIR DE MODULATEURS DE L'ACTIVITÉ DU GPR119

  摘要：

  公开号：

  WO2011014520A3
• 作为产物：
  描述：

  (Z)-3-(dimethylamino)-2-(4-(trifluoromethyl)phenyl)but-2-enenitrile 生成 3-methyl-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

• The Suzuki–Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction
  作者：Lukáš Jedinák、Renáta Zátopková、Hana Zemánková、Alena Šustková、Petr Cankař

  DOI：10.1021/acs.joc.6b02306

  日期：2017.1.6

  The efficient Suzuki–Miyaura cross-coupling reaction of halogenated aminopyrazoles and their amides or ureas with a range of aryl, heteroaryl, and styryl boronic acids or esters has been developed. The method allowed incorporation of problematic substrates: aminopyrazoles bearing protected or unprotected pyrazole NH, as well as the free amino or N-amide group. Direct comparison of the chloro, bromo

  卤代氨基吡唑及其酰胺或脲与一系列芳基，杂芳基和苯乙烯基硼酸或酯的有效Suzuki-Miyaura交叉偶联反应已得到开发。该方法允许掺入有问题的底物：带有保护或未保护的吡唑NH以及自由氨基或N-酰胺基的氨基吡唑。在Suzuki-Miyaura反应中对氯，溴和碘吡唑的直接比较显示，由于降低了脱卤的倾向，Br和Cl衍生物优于碘吡唑。此外，揭示了影响不希望的脱卤副反应的机理和因素。
• PYRIMIDINE DERIVATIVES AND ANALOGS, PREPARATION METHOD AND USE THEREOF
  申请人：Xu Lifeng

  公开号：US20120178915A1

  公开（公告）日：2012-07-12

  This invention relates with the arylheterocycle-fused pyrimidines, derivatives and analogs of formula I: or stereoisomers, tautoers, prodrugs, pharmaceutically acceptable salts, complex salts or solvates thereof, wherein: A-cycle is of 3-8 saturated or unsaturated arylheterocycles or aliheterocyclic, containing 1-4 heteroatoms, B-cycle 5-8 member saturated or unsaturated heterocycle containing 1-4 heteroatoms; X 1 , X 2 , X 3 , X 4 are, independently at each occurrence, C, O, S, Se, N and P elements; R 1 , R 2 , R 3 is a substituent containing alicyclic group, arylcycle group, heterocyclic group, adamantane alkyl, adamantane heterocycle, adamantane analogs, sugar group, hydroxyl group, amino acid group or a combination of the above substituents. This invention also relates with their preparative methods and applications.

  该发明涉及与芳基杂环融合的嘧啶类化合物、衍生物和类似物的公式I：或其立体异构体、互变异构体、前药、药学上可接受的盐、复盐或溶剂化合物，其中：A环是由3-8个饱和或不饱和的芳基杂环或芳杂环组成，含有1-4个杂原子，B环是由5-8个成员的饱和或不饱和杂环组成，含有1-4个杂原子；X1、X2、X3、X4在每次出现时独立地是C、O、S、Se、N和P元素；R1、R2、R3是含有脂环基团、芳环基团、杂环基团、金刚烷烷基、金刚烷杂环、金刚烷类似物、糖基、羟基、氨基酸基团或上述基团的组合的取代基。该发明还涉及它们的制备方法和应用。
• Pyrazolopyrimidines as Potent Stimulators for Transient Receptor Potential Canonical 3/6/7 Channels
  作者：Chunrong Qu、Mingmin Ding、Yingmin Zhu、Yungang Lu、Juan Du、Melissa Miller、Jinbin Tian、Jinmei Zhu、Jian Xu、Meng Wen、AGA Er-Bu、Jule Wang、Yuling Xiao、Meng Wu、Owen B. McManus、Min Li、Jilin Wu、Huai-Rong Luo、Zhengyu Cao、Bing Shen、Hongbo Wang、Michael X. Zhu、Xuechuan Hong

  DOI：10.1021/acs.jmedchem.7b00304

  日期：2017.6.8

  Transient receptor potential canonical 3/6/7 (TRPC3/6/7) are highly homologous receptor-operated nonselective cation channels. Despite their physiological significance, very few selective and potent agonists are available for functional examination of these channels. Using a cell-based high throughput screening approach, a lead compound with the pyrazolopyrimidine skeleton was identified as a TRPC6 agonist. Synthetic schemes for the lead and its analogues were established, and structural activity relationship studies were carried out. A series of potent and direct agonists of TRPC3/6/7 channels were identified, and among them, 4m-4p have a potency order of TRPC3 > C7 > C6, with 4n being the most potent with an EC50 of <20 nM on TRPC3. Importantly, these compounds exhibited no stimulatory activity on related TRP channels. The potent and selective compounds described here should be suitable for evaluation of the roles of TRPC channels in the physiology and pathogenesis of diseases, including glomerulosderosis and cancer.