ethyl 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate | 34760-56-0

• 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: ethyl 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate
• 英文别名: 2,5-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester；Ethyl 2,5-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylate
• CAS: 34760-56-0
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: KGCRMYGBRPUDKY-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2,5-dimethyl-N-(4-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyridine-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Pyrazolo[1,5-a]pyridine-3-carboxamides as Novel Antitubercular Agents

  摘要：

  A series of pyrazolo[1,5-a]pyridine-3-carboxamide derivatives were designed and synthesized as new anti-Mycobacterium tuberculosis (Mtb) agents. The compounds exhibit promising in vitro potency with nanomolar MIC values against the drug susceptive H37Rv strain and a panel of clinically isolated multidrug-resistant Mtb (MDR-TB) strains. One of the representative compounds (5k) significantly reduces the bacterial burden in an autoluminescent H37Ra infected mouse model, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.

  DOI：

  10.1021/acsmedchemlett.5b00176
• 作为产物：
  描述：

  4-甲基吡啶 、 2-丁炔酸乙酯 在 2,4-二硝基苯基羟胺 、 potassium carbonate 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以55.9%的产率得到ethyl 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Pyrazolo[1,5-a]pyridine-3-carboxamides as Novel Antitubercular Agents

  摘要：

  A series of pyrazolo[1,5-a]pyridine-3-carboxamide derivatives were designed and synthesized as new anti-Mycobacterium tuberculosis (Mtb) agents. The compounds exhibit promising in vitro potency with nanomolar MIC values against the drug susceptive H37Rv strain and a panel of clinically isolated multidrug-resistant Mtb (MDR-TB) strains. One of the representative compounds (5k) significantly reduces the bacterial burden in an autoluminescent H37Ra infected mouse model, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.

  DOI：

  10.1021/acsmedchemlett.5b00176

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。
• [EN] DEUTERATED IMIDAZOPYRIDINES<br/>[FR] IMIDAZOPYRIDINES DEUTÉRÉS
  申请人：UNIV NOTRE DAME DU LAC

  公开号：WO2019175737A1

  公开（公告）日：2019-09-19

  A series of imidazopyridine and pyrazolopyridine compounds is provided in which carbon hydrogen bonds have been replaced with isotopic carbon-deuterium bonds, syntheses thereof, compositions thereof, and methods of using such compounds and compositions. Various embodiments provide methods of killing and/or inhibiting the growth of M. tuberculosis and/or M. avium, and methods of treating, preventing, and/or ameliorating M. tuberculosis, M. avium or other mycobacterial infections in a subject like M. leprae or M. ulcerans.

  提供了一系列咪唑吡啶和吡唑吡啶化合物，其中碳氢键已被同位素碳-氘键所取代，以及这些化合物的合成、组成和使用方法。各种实施方式提供了杀灭和/或抑制结核分枝杆菌和/或埃维分枝杆菌生长的方法，以及治疗、预防和/或缓解结核分枝杆菌、埃维分枝杆菌或其他分枝杆菌感染（如麻风分枝杆菌或溃疡分枝杆菌）在受试者中的方法。
• 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。
• PYRAZOLO[1,5-A]PYRIDINES AND THEIR USE IN CANCER THERAPY
  申请人：AUCKLAND UNISERVICES LIMITED

  公开号：EP2176260A1

  公开（公告）日：2010-04-21
• PYRAZOLO[1,5-A]PYRIDINE COMPOUNDS AND USE THEREOF
  申请人：GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH CHINESE ACADEMY OF SCIENCES

  公开号：US20170313697A1

  公开（公告）日：2017-11-02

  Disclosed in the disclosure are a pyrazolo[1,5-a]pyrideine compound with structural features as shown in formula (I) or a pharmaceutically acceptable salt, stereoisomer or prodrug molecule thereof and a use thereof. Such compounds have a good in vitro antituberculosis activity, and the minimal inhibitory concentration (MIC) of the compounds is lower than 0.1 μg/mL and partially achieves 0.01 μg/mL, and have a very strong inhibiting effect on clinically selected multi-drug resistant tuberculosis (MDR-TB) strains. In an in vivo experiment, the pyrazolo[1,5-a]pyrideine compounds of the present disclosure can effectively scavenge the infectious dose of H37Ra in a mouse body at 20 mg/kg/d does, thereby being a new type of antituberculosis compound.