3-isopropyl-1-methyl-1H-pyrazole-4-carbaldehyde | 1152502-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropyl-1-methyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 1-methyl-3-(propan-2-yl)-1H-pyrazole-4-carbaldehyde；1-methyl-3-propan-2-ylpyrazole-4-carbaldehyde
• CAS: 1152502-99-2
• 化学式: C₈H₁₂N₂O
• mdl: MFCD11103096
• 分子量: 152.196
• InChiKey: KQWIBEKKNWQHJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-3-硝基-4-[4-(吡啶-3-基甲基)哌嗪-1-基]吡啶-2-胺 、 3-isopropyl-1-methyl-1H-pyrazole-4-carbaldehyde 在 sodium dithionite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以20%的产率得到6-bromo-2-(3-isopropyl-1-methyl-1H-pyrazol-4-yl)-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo(4,5-b)pyridine
  参考文献：
  名称：

  Discovery of Tyk2 inhibitors via the virtual site-directed fragment-based drug design

  摘要：

  In this study, we synthesized compound 12 with potent Tyk2 inhibitory activity from FBDD study and carried out a cell- based assay for Tyk2/STAT3 signaling activation upon IFN alpha 5 stimulation. Compound 12 completely suppressed the IFN alpha 5-mediated Tyk2/STAT3 signaling pathway as well as the basal levels of pSTAT3. Stimulation with IFN alpha/beta leads to the tyrosine phosphorylation of the JAK1 and Tyk2 receptor-associated kinases with subsequent STATs activation, transmitting signals from the cell surface receptor to the nucleus. In conclusion, the potency of compound 12 to interrupt the signal transmission of Tyk2/STAT3 appeared to be equivalent or superior to that of the reference compound. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.037
• 作为产物：
  描述：

  N-(3-methylbutan-2-ylideneamino)methanamine 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 5.0h， 以73%的产率得到3-isopropyl-1-methyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  N-Alkylhydrazones of aliphatic ketones in the synthesis of 1,3,4-trisubstituted non-symmetric pyrazoles

  摘要：

  Reactions of N-alkylhydrazones of aliphatic ketones with the Vilsmeier-Haack reagent (DMF-POCl3) were evaluated as a promising approach toward the synthesis of trisubstituted non-symmetric pyrazoles. It was found that either 1,3,4-trialkylpyrazoles or 1,3-dialkylpyrazole-4-carbaldehydes could be obtained in these transformations in high yields (72-83%), in a regioselective manner. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.058

文献信息

• SUBSTITUTED PYRAZOLE INHIBITORS OF C-MET PROTEIN KINASE
  申请人：Li Pan

  公开号：US20100305155A1

  公开（公告）日：2010-12-02

  The present invention relates to compounds of formula I, which is useful in the inhibition of c-Met protein kinase. The invention also provides pharmaceutically acceptable compositions comprising compounds of formula I and methods of using the compositions in the treatment of proliferative disorders.

  本发明涉及式I的化合物，该化合物对抑制c-Met蛋白激酶具有作用。本发明还提供了包括式I化合物的药学上可接受的组合物，并提供了使用这些组合物治疗增生性疾病的方法。
• 2‐Oxabicyclo[2.1.1]hexanes: Synthesis, Properties, and Validation as Bioisosteres of <i>ortho</i>‐ and <i>meta</i>‐Benzenes
  作者：Vadym V. Levterov、Yaroslav Panasiuk、Oleh Shablykin、Oleksandr Stashkevych、Kateryna Sahun、Artur Rassokhin、Iryna Sadkova、Dmytro Lesyk、Anna Anisiforova、Yuliia Holota、Petro Borysko、Iryna Bodenchuk、Nataliya M. Voloshchuk、Pavel K. Mykhailiuk

  DOI：10.1002/anie.202319831

  日期：2024.5.6

  substituted 2-oxabicyclo[2.1.1]hexanes has been developed. The obtained compounds have been incorporated into the structure of five drugs and three agrochemicals, and have been validated biologically as bioisosteres of ortho- and meta-benzenes.

  已经开发出一种通用且实用的取代 2-氧杂双环[2.1.1]己烷的方法。所获得的化合物已被纳入五种药物和三种农用化学品的结构中，并已作为邻苯和间苯的生物等排体进行了生物学验证。
• US8269013B2
  申请人：——

  公开号：US8269013B2

  公开（公告）日：2012-09-18
• N-Alkylhydrazones of aliphatic ketones in the synthesis of 1,3,4-trisubstituted non-symmetric pyrazoles
  作者：Sergey P. Ivonin、Bohdan B. Kurpil’、Eduard B. Rusanov、Oleksandr O. Grygorenko、Dmitry M. Volochnyuk

  DOI：10.1016/j.tetlet.2014.02.058

  日期：2014.4

  Reactions of N-alkylhydrazones of aliphatic ketones with the Vilsmeier-Haack reagent (DMF-POCl3) were evaluated as a promising approach toward the synthesis of trisubstituted non-symmetric pyrazoles. It was found that either 1,3,4-trialkylpyrazoles or 1,3-dialkylpyrazole-4-carbaldehydes could be obtained in these transformations in high yields (72-83%), in a regioselective manner. (C) 2014 Elsevier Ltd. All rights reserved.
• Discovery of Tyk2 inhibitors via the virtual site-directed fragment-based drug design
  作者：Woo Dae Jang、Jun-Tae Kim、Hoon Young Son、Seung Yeon Park、Young Sik Cho、Tae-sung Koo、Hyuk Lee、Nam Sook Kang

  DOI：10.1016/j.bmcl.2015.07.037

  日期：2015.9

  In this study, we synthesized compound 12 with potent Tyk2 inhibitory activity from FBDD study and carried out a cell- based assay for Tyk2/STAT3 signaling activation upon IFN alpha 5 stimulation. Compound 12 completely suppressed the IFN alpha 5-mediated Tyk2/STAT3 signaling pathway as well as the basal levels of pSTAT3. Stimulation with IFN alpha/beta leads to the tyrosine phosphorylation of the JAK1 and Tyk2 receptor-associated kinases with subsequent STATs activation, transmitting signals from the cell surface receptor to the nucleus. In conclusion, the potency of compound 12 to interrupt the signal transmission of Tyk2/STAT3 appeared to be equivalent or superior to that of the reference compound. (C) 2015 Elsevier Ltd. All rights reserved.