3-(4-ethylphenyl)-1H-pyrazol-5-amine

• 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-(4-ethylphenyl)-1H-pyrazol-5-amine
• 英文别名: 5-(4-ethylphenyl)-1H-pyrazol-3-amine
• 化学式: C₁₁H₁₃N₃
• mdl: MFCD02664123
• 分子量: 187.244
• InChiKey: JTJUUTBMBCHAFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-ethylphenyl)-1H-pyrazol-5-amine 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 生成 6-(4-carboxy-3-fluorophenyl)-3-(4-ethylphenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid
  参考文献：
  名称：

  通过高通量筛选发现新型化学系列 OXA-48 β-内酰胺酶抑制剂

  摘要：

  细菌对β-内酰胺类耐药的主要原因是产生水解β-内酰胺酶。如今，β-内酰胺类抗生素与β-内酰胺酶抑制剂（BLI）的组合是克服这些问题的主要策略。然而，特别具有挑战性的 β-内酰胺酶，如 OXA-48，需要新的和有效的治疗方法。在此，我们描述了针对肺炎克雷伯菌OXA-48的专有化合物集合的筛选，从而鉴定了几种化学型，如 4-ideneamino-4H-1,2,4-三唑 (SC_2) 和吡唑并 [3,4 -b] 吡啶 (SC_7) 核心作为潜在的抑制剂。重要的是，后者系列（ID2、AC 50= 0.99 μM) 通过可逆和竞争性作用机制抑制 OXA-48，如生化和 X 射线研究所示；此外，它略微提高了亚胺培南在大肠杆菌ATCC BAA-2523 β-内酰胺抗性菌株中的活性。此外，ID2显示出良好的溶解性，并且在最高测试浓度下没有毒性迹象，这为进一步优化程序以开发新型有效的非 β-内酰胺 BLI 提供了一个有希望的起点。

  DOI：

  10.3390/ph14070612
• 作为产物：
  描述：

  4-乙基苯甲酸甲酯 在 正丁基锂 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.0h， 生成 3-(4-ethylphenyl)-1H-pyrazol-5-amine
  参考文献：
  名称：

  [EN] 5- OR 7-AZAINDAZOLES AS BETA-LACTAMASE INHIBITORS
  [FR] AZAINDAZOLES EN 5 OU 7 UTILISÉS COMME INHIBITEURS DE BÊTA-LACTAMASE

  摘要：

  本发明涉及具有以下一般式（I）的β-内酰胺酶抑制剂：其中R1-R4和X1-X2在规范中定义，其药物组成物，以及其用于治疗细菌感染的用途，单独或与β-内酰胺类抗生素和/或其他抗生素和/或其他β-内酰胺酶抑制剂结合使用。

  公开号：

  WO2020178316A1

文献信息

• Pharmacologically active aryl-substituted pyrazolo[1,5-a]pyrimidine derivatives
  申请人：RICHTER GEDEON NYRT.

  公开号：US10960007B2

  公开（公告）日：2021-03-30

  The present invention relates to new pyrazolo[1,5-a]pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof that serve as GABAB receptor positive allosteric modulators. The invention also relates to the process for producing such compounds. The invention further relates to pharmaceutical compositions comprising such compounds optionally in combination with two or more different therapeutic agents and the use of such compounds in methods for treating diseases and conditions mediated and modulated by the GABAB receptor positive allosteric mechanism. The invention also provides a method for manufacture of medicaments useful in the treatment of such disorders.

  本发明涉及新的式（I）吡唑并[1,5-a]嘧啶衍生物或其药学上可接受的盐、生物活性代谢物、原药、外消旋体、对映体、非对映异构体、溶液和水合物，可作为 GABAB 受体正异位调节剂。本发明还涉及生产此类化合物的工艺。本发明进一步涉及包含此类化合物的药物组合物（可选择与两种或两种以上不同的治疗剂组合），以及此类化合物在治疗由 GABAB 受体正性异位调节机制介导和调节的疾病和病症的方法中的用途。本发明还提供了一种用于治疗此类疾病的药物的制造方法。
• Cyclocondensation reactions of 5-aminopyrazoles, pyruvic acids and aldehydes. Multicomponent approaches to pyrazolopyridines and related products
  作者：Valentin A. Chebanov、Yana I. Sakhno、Sergey M. Desenko、Vitaliy N. Chernenko、Vladimir I. Musatov、Svetlana V. Shishkina、Oleg V. Shishkin、C. Oliver Kappe

  DOI：10.1016/j.tet.2006.11.048

  日期：2007.1

  The reactions of 3-substituted 5-aminopyrazoles with arylidenepyruvic acids and their synthetic precursors, pyruvic acid and aromatic aldehydes, were studied. Several different reaction pathways for these cyclocondensation reactions were established depending on the reaction conditions and building block selection. The formation of pyrazolo[3,4-b]pyridine-6-carboxylic acids as major products and related compounds was discussed from the mechanistic point of view. (c) 2006 Elsevier Ltd. All rights reserved.
• Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products
  作者：Maryna V. Murlykina、Yana I. Sakhno、Sergey M. Desenko、Iryna S. Konovalova、Oleg V. Shishkin、Dmytro A. Sysoiev、Maryna N. Kornet、Valentin A. Chebanov

  DOI：10.1016/j.tet.2013.08.055

  日期：2013.11

  Three-component reactions of 5-aminopyrazoles and salicylic aldehydes with pyruvic acids were studied. The method of tuning of the selectivity of the heterocyclizations allowing to change its direction by variation of the reaction parameters was worked out. The treatment involving pyruvic acid can be selectively directed to the formation to either 3-aryl-10,11-dihydro-4,10-methano-pyrazolo[4,3-c][1,5]benzoxazocine-4-carboxylic acids or 3,6-diarylpyrazolo[3,4-b]pyridine-4-carboxylic acids, while the reaction involving arylpyruvic acid leads only to 7-hydroxy-2,5,6-triaryl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidine-7-carboxylic acids. Antimicrobial activity of the compounds obtained was also studied: Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) were found sensitive to the substances tested, however, only in the highest concentration. (C) 2013 Elsevier Ltd. All rights reserved.
• Pharmacologically Active Aryl-Substituted Pyrazolo[1,5-a]Pyrimidine Derivatives
  申请人：RICHTER GEDEON NYRT.

  公开号：US20200061068A1

  公开（公告）日：2020-02-27

  The present invention relates to new pyrazolo[1,5-a]pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof that serve as GABA B receptor positive allosteric modulators. The invention also relates to the process for producing such compounds. The invention further relates to pharmaceutical compositions comprising such compounds optionally in combination with two or more different therapeutic agents and the use of such compounds in methods for treating diseases and conditions mediated and modulated by the GABA B receptor positive allosteric mechanism. The invention also provides a method for manufacture of medicaments useful in the treatment of such disorders.