2-methyl-3-pyrazolo<1,5-a>pyridinecarboxaldehyde | 119666-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 2-methyl-3-pyrazolo<1,5-a>pyridinecarboxaldehyde
• 英文别名: 2-methyl-pyrazolo[1,5-a]pyridine-3-carbaldehyde；3-formyl-2-methylpyrazolo[1,5-a]pyridine；2-methylpyrazolo[1,5-a]pyridine-3-carbaldehyde
• CAS: 119666-15-8
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: FEFXMZXYRUTYDK-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-pyrazolo<1,5-a>pyridinecarboxaldehyde 在 三氟化硼 、 ammonium acetate 、 羟胺 、 sodium methylate 、 碳酸氢钠 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 49.0h， 生成 (E)-N-hydroxy-3-(4-{[2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)ethylamino]methyl}phenyl)acrylamide
  参考文献：
  名称：

  Optimization of the in Vitro Cardiac Safety of Hydroxamate-Based Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent. HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree, of pharmacophore homology between these two targets was discovered. This, similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homology model, two compounds, 11r and 25i, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

  DOI：

  10.1021/jm200388e
• 作为产物：
  描述：

  2-methylpyrazolo<1,5-α>pyridine 在 三氯氧磷 作用下， 以 N-甲基乙酰胺 为溶剂， 生成 2-methyl-3-pyrazolo<1,5-a>pyridinecarboxaldehyde
  参考文献：
  名称：

  Certain

  摘要：

  本发明涉及以下式的新型有用的2,6-二甲基-4-(吡唑并[1,5-a]吡啶-3-基)-1,4-二氢-吡啶-3,5-二羧酸酯衍生物： ##STR1## 和其药学上可接受的盐，具有促进某些抗肿瘤药物对各种肿瘤细胞，包括多药耐药肿瘤细胞的强效促进作用。

  公开号：

  US04923871A1

文献信息

• [EN] PYRAZOLO[1,5-A]PYRIDINES AND THEIR USE IN CANCER THERAPY<br/>[FR] PYRAZOLO[1,5-A]PYRIDINES ET LEUR UTILISATION EN CANCÉROTHÉRAPIE
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2009008748A1

  公开（公告）日：2009-01-15

  Pyrazolo[1,5-a]pyridines are described, including methods for their preparation, and their use as agents or drugs for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  Pyrazolo[1,5-a]吡啶类化合物被描述，包括它们的制备方法，以及它们作为抗癌治疗药物或药剂的用途，无论是单独使用还是与放疗和/或其他抗癌药物联合使用。
• Pyrazolo-Pyridine Derivatives As Antiherpes Agents
  申请人：Gudmundsson Kristjan

  公开号：US20070161653A1

  公开（公告）日：2007-07-12

  The present invention provides compounds of formula (I): wherein all variables are as defined herein, pharmaceutical compositions containing the same, processes for preparing the same and their use as pharmaceutical agents.

  本发明提供公式(I)的化合物：其中所有变量均如此定义，包含该化合物的药物组合物，制备该化合物的过程以及它们作为药物制剂的用途。
• PYRAZOLO[1,5-a]PYRIDINES AND THEIR USE IN CANCER THERAPY
  申请人：Kendall Jackie Diane

  公开号：US20100226881A1

  公开（公告）日：2010-09-09

  Pyrazolo[1,5-a]pyridines are described, including methods for their preparation, and their use as agents or drugs for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本文描述了Pyrazolo[1,5-a]pyridines，包括其制备方法，以及其作为单独或与放射治疗和/或其他抗癌药物联合使用的癌症治疗药物或代理。
• Pyrazolopyridines. 1. Formylation and Acylation of Pyrazolo[1,5-a]pyridines
  作者：Ken-ichi Tanji、Takehiko Sasahara、Junko Suzuki、Takeo Higashino

  DOI：10.3987/com-92-s(t)85

  日期：——

  In the treatment of pyrazolo[1,5-a]pyridines with dimethylformamide and,phosphorus oxychloride, Vilsmeier-Haack formylation proceeded at the 3-position, giving 3-pyrazolo[1,5-a]pyridinecarboxaldehydes. Reaction of the pyrazolo[1,5-a]pyridine with acyl halide gave 3-acylpyrazolo[1,5-a]pyridines. Conversion of the formyl group into the alkenyl group was achieved easily by Wittig reaction.
• Agents promoting the activity of some antitumor agents and methods for their production
  申请人：KYORIN SEIYAKU KABUSHIKI KAISHA

  公开号：EP0270926B1

  公开（公告）日：1993-03-17