5-amino-3-phenyl-1-(pyridin-2-yl)-1H-pyrazole | 58589-70-1

• 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
• 英文名称: 5-amino-3-phenyl-1-(pyridin-2-yl)-1H-pyrazole
• 英文别名: 3-phenyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine；1-Pyridyl-3-phenyl-5-aminopyrazole；5-phenyl-2-pyridin-2-ylpyrazol-3-amine
• CAS: 58589-70-1
• 化学式: C₁₄H₁₂N₄
• mdl: MFCD11558580
• 分子量: 236.276
• InChiKey: IYCQPIBNWGOQSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-3-phenyl-1-(pyridin-2-yl)-1H-pyrazole 在 碘苯二乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以93%的产率得到(Z)-3-phenyl-3-((E)-pyridin-2-yldiazenyl)acrylonitrile
  参考文献：
  名称：

  PIDA-mediated oxidative aromatic C N bond cleavage: Efficient methodology for the synthesis of 1,2-diaza-1,3-dienes under ambient conditions

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153252
• 作为产物：
  描述：

  苯甲腈 在 盐酸 、 potassium tert-butylate 作用下， 以 苯 为溶剂， 反应 24.33h， 生成 5-amino-3-phenyl-1-(pyridin-2-yl)-1H-pyrazole
  参考文献：
  名称：

  Substituent Effects of N-(1,3-Diphenyl-1H-pyrazol-5-yl)benzamides on Positive Allosteric Modulation of the Metabotropic Glutamate-5 Receptor in Rat Cortical Astrocytes

  摘要：

  CDPPB [3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl) benzamide] was recently described as the first centrally active, positive allosteric modulator of rat and human metabotropic glutamate receptor (mGluR) mGluR(5) subtype. We explored the structural requirements for potentiation of glutamate-induced calcium release in naturally expressed mGluR5 in cultured rat astrocytes and increasing affinity for the allosteric antagonist binding site by evaluating 50 analogues of CDPPB. In the fluorometric calcium assay, CDPPB exhibited an EC50 value of 77 +/- 15 nM in potentiating mGluR(5)-mediated responses in cortical astrocytes and a K-i value of 3760 ( 430 nM in displacing [H-3] methoxyPEPy binding in membranes of cultured HEK-293 cells expressing rat mGluR5. The structure-activity relationships showed that electronegative aromatic substituents in the para-position of the benzamide moiety of CDPPB increase potency. Both binding and functional activities were further increased with a halogen atom in the ortho-position of the 1-phenyl ring. These effects of substitution do not match those of either aromatic ring of MPEP [2-methyl-6-(phenylethynyl)-pyridine] for the antagonist allosteric binding site. Combination of the optimal substituents and aromatic positions resulted in 4-nitro-N-(1-(2-fluorophenyl)-3-phenyl-1H-pyrazol-5-yl) benzamide (VU-1545) showing K-i) 156 (29 nM and EC50) 9.6 (1.9 nM in the binding and functional assays, respectively.

  DOI：

  10.1021/jm051252j

文献信息

• Condensed pyrazole derivatives, process for producing the same and use thereof
  申请人：——

  公开号：US20030187014A1

  公开（公告）日：2003-10-02

  Novel pharmaceutical compositions for inhibiting Th2-selective immune response and pharmaceutical compositions for inhibiting cyclooxygenase comprising condensed pyrazole derivatives represented by the general formula (I): 1 or salts thereof.

  用于抑制Th2选择性免疫应答的新型药物组合物和包括由一般式(I)表示的紧缩吡唑烷衍生物的药物组合物，或其盐。
• Evaluation of Electrophilic Heteroaromatic Substitution: Synthesis of Heteroaromatic-Fused Pyrimidine Derivatives via Sequential Three-Component Heterocyclization
  作者：Fung Fuh Wong、Yu-Ying Huang、Chun-Hsi Chang

  DOI：10.1021/jo301463m

  日期：2012.10.5

  A new sequential three-component heterocyclization was developed by reacting aromatic and heterocyclic substrates, including aminobenzenes, 1-aminonaphthalene, 2-aminopyrazines, 5-aminopyrazoles, 3-aminopyridine, 5-aminopyrimidine, 5-aminoquinoline, and 8-aminoquinoline, with formamide in the presence of PBr3. The reaction gave the corresponding pyrazolo[3,4-d]pyrimidines in good yields (59–96%), except

  通过使芳香族和杂环底物（包括氨基苯，1-氨基萘，2-氨基吡嗪，5-氨基吡唑，3-氨基吡啶，5-氨基嘧啶，5-氨基喹啉和8-氨基喹啉）与甲酰胺反应，开发了一种新的顺序三组分杂环化方法在PBr 3存在下。除氨基苯和3-氨基吡啶外，该反应以较高的收率（59-96％）得到了相应的吡唑并[3,4- d ]嘧啶。提出了包括三步酰胺化，亲电取代亚胺化和氧化环化的合理反应机理，以解决杂环化问题。发现反应的反应性与芳族或杂环底物的亲电子性成比例。
• Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl)formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents
  作者：Chun-Hsi Chang、Henry J. Tsai、Yu-Ying Huang、Hui-Yi Lin、Li-Ya Wang、Tian-Shung Wu、Fung Fuh Wong

  DOI：10.1016/j.tet.2012.11.002

  日期：2013.1

  N-1-(2-pyridinyl)-5-aminopyrazoles, and N-1-(2-quinolinyl)-5-aminopyrazoles with these agents gave the corresponding pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl)formamide, or N-(1H-pyrazol-5-yl)formamidine. The reaction was different from the traditional Vilsmeier-type reaction and the plausible reactive pathways were proposed for the unexpected result.

  从甲酰胺或N-甲基甲酰胺与POCl 3合成了多种新型的Vilsmeier试剂卤代甲基亚铵盐。的治疗Ñ -1-取代的氨基吡唑包括Ñ -1-苯基-5-氨基吡唑，Ñ -1-（2-吡啶基）-5-氨基吡唑，和Ñ -1-（2-喹啉基）-5-氨基吡唑与这些剂得到相应的吡唑并[3,4- d ]嘧啶，N-（1 H-吡唑-5-基）甲酰胺或N-（1 H-吡唑-5-基）甲idine。该反应不同于传统的Vilsmeier型反应，并提出了可能的反应途径以取得意想不到的结果。
• Structures, Phase Behavior, and Fluorescent Properties of 3-Phenyl-1-(pyridin-2-yl)-1<i>H</i>-pyrazol-5-amine and Its ZnCl₂ Complex
  作者：Lana K. Hiscock、Delara Joekar、Barbora Balonova、Marta Tomas Piqueras、Zachary W. Schroeder、Victoria Jarvis、Kenneth E. Maly、Barry A. Blight、Louise N. Dawe

  DOI：10.1021/acs.inorgchem.9b02765

  日期：2019.12.16

  ligand 3-phenyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine (L1) and its single-crystal X-ray structure are reported. L1 displays crystallographic symmetry (orthorhombic, Pccn) higher than its molecular symmetry (point group C1) and also displays supercooling, with a difference in the melting and solidification points of over 100 °C. Upon complexation with ZnCl2, L1 engages in both primary cation and secondary

  报道了不对称配体3-苯基-1-（吡啶-2-基）-1H-吡唑-5-胺（L1）的合成及其单晶X射线结构。L1的晶体对称性（斜方晶系，Pccn）高于其分子对称性（点组C1），并且还表现出过冷状态，其熔点和凝固点之差超过100°C。与ZnCl2络合后，L1通过氢键参与伯阳离子和仲阴离子的配位，并且该络合物表现出从室温到低温的单晶到晶体的相变。ZnCl 2络合物变成双折射流体，在高温下与晶畴混合，这是通过偏振光学显微镜检测到的。
• N-alkyl pyrroles as HMG-CoA reductase inhibitors
  申请人：Bratton D. Larry

  公开号：US20050154042A1

  公开（公告）日：2005-07-14

  HMGCo-A reductase inhibitor compounds useful as hypocholesterolemic and hypolipidemic compounds are provided. Also provided are pharmaceutical compositions of the compounds. Methods of making and methods of using the compounds are also provided.

  提供了作为降低胆固醇和降脂化合物有用的HMGCo-A还原酶抑制剂化合物。还提供了该化合物的药物组成物。还提供了制备该化合物的方法和使用该化合物的方法。