4-吡啶基-3-2H-吡唑-3-胺 | 40545-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-吡啶基-3-2H-吡唑-3-胺
• 中文别名: 2-氨基-4-(3-吡啶)基吡唑
• 英文名称: 4-pyridin-3-yl-2H-pyrazol-3-ylamine
• 英文别名: 4-pyridin-3-yl-1(2)H-pyrazol-3-ylamine；4-(pyridin-3-yl)-1H-pyrazol-5-amine；4-pyridin-3-yl-1H-pyrazol-5-amine
• CAS: 40545-68-4
• 化学式: C₈H₈N₄
• mdl: MFCD07357373
• 分子量: 160.178
• InChiKey: XFTJTKIDLRCJBT-UHFFFAOYSA-N

物化性质

• 沸点：
  433.5±35.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-吡啶基-3-2H-吡唑-3-胺 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-3-ylpyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Optimization of a pyrazolo[1,5-a]pyrimidine class of KDR kinase inhibitors: improvements in physical properties enhance cellular activity and pharmacokinetics

  摘要：

  We have introduced solubilizing functionality to a 3,6-disubstituted pyrazolo[1,5-a]pyrimidine series of KDR kinase inhibitors to improve the physical properties of these compounds. The addition of a basic side-chain to the 6-aryl ring, introduction of 3-pyridyl groups, and most significantly, incorporation of a 4-pyridinonyl substituent at the 6-position of the core are modifications that maintain and often enhance the intrinsic potency of this class of inhibitors. Moreover, the improvements in physical properties result in marked increases in cellular activity and more favorable pharmacokinetics in rats. The synthesis and SAR of these compounds are described.(C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00827-2
• 作为产物：
  描述：

  3-吡啶乙腈 在 氢溴酸肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-吡啶基-3-2H-吡唑-3-胺
  参考文献：
  名称：

  Development of a Reproducible and Scalable Method for the Synthesis of Biologically Active Pyrazolo[1,5-a]pyrimidine Derivatives

  摘要：

  摘要 为合成一系列 3,6 取代的吡唑并[1,5-a]嘧啶开发了一种可重复和可扩展的方法，该方法是合理设计 AMP 活化蛋白激酶选择性抑制剂的基础。关于新型碳骨架的形成，利用布赫瓦尔德配体在 5,7 二甲基取代的吡唑并[1,5-a]嘧啶的立体受阻位置 6 上形成 C-C 键的 Suzukii-Miyaura 交叉偶联的适用性已经得到证明。

  DOI：

  10.1134/s1070363223050043

文献信息

• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120277224A1

  公开（公告）日：2012-11-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• [EN] PIPERIDINYLPYRAZOLOPYRIMIDINONES AND THEIR USE<br/>[FR] PIPÉRIDINYLPYRAZOLOPYRIMIDINONES ET LEUR UTILISATION
  申请人：BAYER PHARMA AG

  公开号：WO2016071216A1

  公开（公告）日：2016-05-12

  The present application relates to novel substituted piperidinylpyrazolopyrimidinones, to processes for their preparation, the compounds for use alone or in combinations in a method for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of acute and recurrent bleeding in patients with or without underlying hereditary or acquired hemostatic disorders, wherein the bleeding is associated with a disease or medical intervention selected from the group consisting of heavy menstrual bleeding, postpartum hemorrhage, hemorrhagic shock, hemorrhagic cystitis, gastrointestinal hemorrhage, trauma, surgery, transplantation, stroke, liver diseases, hereditary angioedema, nosebleed, and synovitis and cartilage damage following hemarthrosis.

  本申请涉及新型取代哌啶基吡唑吡嘧啶酮，以及它们的制备方法，这些化合物可单独或组合使用于治疗和/或预防疾病的方法中，特别是用于治疗和/或预防患有或不患有基础遗传或获得性止血障碍的患者的急性和复发性出血，其中出血与从重经期出血、产后出血、出血性休克、出血性膀胱炎、胃肠道出血、创伤、手术、移植、中风、肝脏疾病、遗传性血管性水肿、鼻血、以及血液积聚后的滑膜炎和软骨损伤等一组疾病或医疗干预有关。
• [EN] PYRAZOLO AND IMIDAZO-PYRIMIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRAZOLO-PYRIMIDINE ET D'IMIDAZO-PYRIMIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005040171A1

  公开（公告）日：2005-05-06

  The present invention relates to novel pyrazolo- and imidazo-pyrimidine derivatives of formula (I) wherein A, D, E, L, M, Q, R1, R2 and R3 are as defined in the description and claims and to processes for their preparation, pharmaceutical compositions containing said derivatives and their use in the prevention and treatment of diseases.

  本发明涉及公式（I）中的新型吡唑啉和咪唑嘧啶衍生物，其中A、D、E、L、M、Q、R1、R2和R3如描述和索赔中所定义，并涉及其制备方法、含有所述衍生物的药物组合物以及它们在预防和治疗疾病中的用途。
• A new class of pyrazolo[5,1-c][1,2,4]triazines as γ-aminobutyric type A (GABAA) receptor subtype ligand: synthesis and pharmacological evaluation
  作者：Gabriella Guerrini、Giovanna Ciciani、Simona Daniele、Claudia Martini、Camilla Costagli、Chiara Guarino、Silvia Selleri

  DOI：10.1016/j.bmc.2018.04.011

  日期：2018.5

  between compounds with pyrazolo[1,5-a]pyrimidine structure (series 4-6) and pyrazolo[5,1-c][1,2,4]triazine core (series 9) as ligands at GABAA-receptor subtype, was evaluated. Moreover, for pyrazolotriazine derivatives having binding recognition, the interaction on recombinant rat α(1-3,5) GABAA receptor subtypes, was performed. Among these latter, emerge compounds 9c, 9k, 9l, 9m and 9n as α1-selective

  以吡唑并[1,5-a]嘧啶结构（4-6系列）和吡唑并[5,1-c] [1,2,4]三嗪核心（9系列）为配体的化合物在GABAA受体亚型之间的比较，进行了评估。此外，对于具有结合识别的吡唑并三嗪衍生物，进行了对重组大鼠α（1-3,5）GABAA受体亚型的相互作用。在这些化合物中，出现了化合物9c，9k，9l，9m和9n作为α1选择性配体，而9h作为α2选择性配体。
• Synthesis and pharmacological evaluation of pyrazolo[1,5-a]pyrimidin-7(4H)-one derivatives as potential GABAA-R ligands
  作者：Gabriella Guerrini、Giovanna Ciciani、Simona Daniele、Lorenzo Di Cesare Mannelli、Carla Ghelardini、Claudia Martini、Silvia Selleri

  DOI：10.1016/j.bmc.2017.02.013

  日期：2017.3

  The synthesis of a new series of 6-phenyl- and 6-benzylpyrazolo[1,5-a]pyrimidin-7(4H)-ones 2a-g and 3a-g, strictly related to derivatives with pyrazolobenzotriazine (PBT) and pyrazoloquinazoline (PQ) scaffold, was realized. The in vitro GABAA-receptor subtype affinity was evaluated and from preliminary pharmacological studies, compound 3g shows anxiolytic-like effect at 10-30mg/kg.

  一系列新的6-苯基-和6-苄基吡唑并[1,5-a]嘧啶7（4H）-酮2a-g和3a-g的合成，这些衍生物与吡唑并苯并三嗪（PBT）和吡唑并喹唑啉的衍生物严格相关（ PQ）脚手架，已实现。评估了体外GABAA-受体亚型的亲和力，并从初步药理学研究中，化合物3g在10-30mg / kg时显示出抗焦虑样作用。