ethyl 3-(dimethoxymethyl)-1H-pyrazole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(dimethoxymethyl)-1H-pyrazole-5-carboxylate
• 英文别名: 5-dimethoxymethyl-1H-pyrazole-3-carboxylic acid ethyl ester；ethyl 5-(dimethoxymethyl)-1H-pyrazole-3-carboxylate
• 化学式: C₉H₁₄N₂O₄
• 分子量: 214.221
• InChiKey: GSFKYFXBEOZABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(dimethoxymethyl)-1H-pyrazole-5-carboxylate 在 甲酸 作用下， 反应 1.0h， 以1.50 g的产率得到5-甲酰基吡唑-3-甲酸乙酯
  参考文献：
  名称：

  1,3-偶极环加成反应合成吡唑基取代的硝酰基硝基氧

  摘要：

  基于通过 1,3-偶极环加成制备的预合成吡唑衍生物，开发了一种合成多功能吡唑基取代的硝酰基氮氧化物的新方法。通过 X 射线衍射证实了所得单自由基和双自由基的结构。

  DOI：

  10.1007/s11172-006-0093-6
• 作为产物：
  描述：

  ethyl 5,5-dimethoxy-2,4-dioxopentanoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以93.1 %的产率得到ethyl 3-(dimethoxymethyl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  含吡唑-5-甲酰胺基序的芳基异恶唑啉衍生物的设计、合成、杀虫活性和比吸收率

  摘要：

  由于农药抗性不断增强，开发具有新作用方式的新型杀虫剂非常重要。本研究设计并合成了一系列含有吡唑-5-甲酰胺基序的新型芳基异恶唑啉衍生物。它们的结构均通过1 H NMR、13 C NMR 和 HRMS 进行了确认。生物测定表明，合成的24个化合物对粘虫具有良好的杀虫活性，但对豆蚜和朱砂叶螨无活性。这些芳基异恶唑啉衍生物中，3-(5-(3，5-二氯苯基)-5-(三氟甲基)-4，5-二氢唑-3-基)-N-( 4-氟苯基)-1-甲基-1H -吡唑-5-甲酰胺( IA-8 )对分枝小蠹的杀虫活性最好，与阳性对照氟拉纳相当。化合物IA-8与氟拉拉纳与GABA模型的分子对接结果表明，化合物IA-8与阳性对照氟拉拉纳在GABA活性位点上的对接模式相同。分子结构比较和 ADMET 分析有可能用于设计更具活性的化合物。还讨论了结构-活性关系。这项工作为进一步优化提供了一种优良的杀虫剂。

  DOI：

  10.1021/acs.jafc.3c01608

文献信息

• 1,3-Dipolar cycloaddition in the synthesis of pyrazolyl-substituted nitronyl nitroxides
  作者：E. V. Tretyakov、S. E. Tolstikov、G. V. Romanenko、Yu. G. Shvedenkov、R. Z. Sagdeev、V. I. Ovcharenko

  DOI：10.1007/s11172-006-0093-6

  日期：2005.9

  A new approach to the synthesis of polyfunctional pyrazolyl-substituted nitronyl nitroxides was developed based on the presynthesized pyrazole derivatives prepared by 1,3-dipolar cycloaddition. The structures of the resulting mono-and biradicals were confirmed by X-ray diffraction.

  基于通过 1,3-偶极环加成制备的预合成吡唑衍生物，开发了一种合成多功能吡唑基取代的硝酰基氮氧化物的新方法。通过 X 射线衍射证实了所得单自由基和双自由基的结构。
• [EN] 5-SUBSTITUTED 2H-PYRAZOLE-3-CARBOXYLIC ACID DERIVATIVES AS AGONISTS FOR THE NICOTINIC ACID RECEPTOR RUP25 FOR THE TREATMENT OF DYSLIPIDEMIA AND RELATED DISEASES<br/>[FR] DERIVES D'ACIDE 2H-PYRAZOL-3- CARBOXYLIQUE SUBSTITUES EN 5 UTILISES COMME AGONISTES DU RECEPTEUR DE L'ACIDE NICOTINIQUE RUP25 POUR LE TRAITEMENT DES DYSLIPIDEMIES ET DES PATHOLOGIES APPARENTEES
  申请人：ARENA PHARM INC

  公开号：WO2005011677A1

  公开（公告）日：2005-02-10

  The present invention relates to certain pyrazole carboxylic acid and ester derivatives, and pharmaceutically acceptable salts thereof, which exhibit useful pharmaceutical properties, for example as agonists for the RUP25 receptor. (I) Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α -glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.the substituents are defined in claim 1.

  本发明涉及某些吡唑羧酸和酯衍生物及其药学上可接受的盐，这些衍生物具有有用的药理特性，例如作为RUP25受体的激动剂。本发明还提供了含有该发明化合物的药物组合物，并且提供了使用该发明化合物和组合物在预防或治疗代谢相关疾病，包括血脂异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、X综合症等方面的方法。此外，本发明还提供了与其他活性剂（例如属于α-葡萄糖苷酶抑制剂、醛还原酶抑制剂、双胍类药物、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、纤维酸类药物、LDL降解增强剂、血管紧张素转换酶（ACE）抑制剂、胰岛素分泌增强剂等类别的）联合使用的本发明化合物的用途。取代基定义详见权利要求书第1项。
• 5-Substituted 2h-pyrazole-3-carboxylic acid derivatives as agonists for the acid receptor rup25 for the treatment of dyslipidemia and related diseases
  申请人：Semple Graeme

  公开号：US20070032537A1

  公开（公告）日：2007-02-08

  The present invention relates to certain pyrazole carboxylic acid and ester derivatives, and pharmaceutically acceptable salts thereof, which exhibit useful pharmaceutical properties, for example as agonists for the RUP25 receptor. (I) Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α-glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like the substituents are defined in claim 1.

  本发明涉及某些吡唑羧酸和酯衍生物及其药学上可接受的盐，其表现出有用的药理特性，例如作为RUP25受体的激动剂。此外，本发明还提供了含有本发明化合物的药物组合物，以及使用本发明化合物和组合物在代谢相关疾病的预防或治疗中的方法，包括血脂异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、X综合症等。此外，本发明还提供了将本发明化合物与其他活性剂（如属于α-葡萄糖苷酶抑制剂、醛还原酶抑制剂、双胍类、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、纤维酸类、LDL降解增强剂、血管紧张素转化酶（ACE）抑制剂、胰岛素分泌增强剂等类别的）联合使用的方法。其中，取代基在权利要求1中定义。
• 一类含三氟甲基噁二唑类衍生物、其制备方法及应用
  申请人：浙江省化工研究院有限公司

  公开号：CN115594670A

  公开（公告）日：2023-01-13

  本发明公开了一种通式A‑1所示的含三氟甲基噁二唑类衍生物： 各取代基见说明书。本发明还公开了所述含三氟甲基噁二唑类衍生物的制备方法及用途，所述含三氟甲基噁二唑类衍生物尤其适用于防治大豆锈病、小麦锈病、玉米锈病、作物炭疽病等。
• Design, Synthesis and Insecticidal Activity of 1-Methyl-3-(5-aryl-4,5-dihydroisoxazol-3-yl)-1H-pyrazole-5-carboxamides
  作者：Chengxia Tan、Jing Yuan、Liangkun Zhong、Tao Jiang、Xinghai Liu、Chengrong Ding、Tianming Xu、Jie Chen

  DOI：10.3987/com-19-14067

  日期：——

  Pyrazole and its derivatives are a kind of important heterocyclic compounds used in agrochemicals development. In this research, a series of novel 1-methyl-3-(5-aryl-4,5-dihydroisoxazol-3-yl)-1H-pyrazole-5-carboxam ides were synthesized and confirmed by H-1 NMR, C-13 NMR and ESI-MS. The preliminary bioactivity indicated that most title compounds showed excellent potency against Mythimna separate (Walker) at 500 mg/L, compounds ZJ4, ZJ12, ZJ16, ZJ17 showed moderate insecticidal activity against Aphis craccivora at 500 mg/L. Especially, compounds ZJ4, ZJ12, ZJ17 exhibited around 60% insecticidal activities against M separate at 100 mg/L. The results indicated that the potential of these pyrazole-5-carboxamides containing arylisoxazoline fragment to be utilized in pesticide discovery through further development.