1-Butyl-5-amino-4-cyan-pyrazol | 90434-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-Butyl-5-amino-4-cyan-pyrazol
• 英文别名: 5-amino-1-butyl-1H-pyrazole-4-carbonitrile；1-n-butyl-4-cyano-5-aminopyrazole；5-Amino-1-butylpyrazole-4-carbonitrile
• CAS: 90434-89-2
• 化学式: C₈H₁₂N₄
• 分子量: 164.21
• InChiKey: VNQWYAWATIOYNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Butyl-5-amino-4-cyan-pyrazol 以 二苯醚 、 乙二醇甲醚 为溶剂， 反应 9.5h， 生成 7-n-butyl-2-(2-furyl)pyrazolo<4,3-e>-1,2,4-triazolo<1,5-c>pyrimidine
  参考文献：
  名称：

  Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine Derivatives:  Potent and Selective A_2A Adenosine Antagonists

  摘要：

  A series of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives (10a-o,q,r), bearing alkyl and aralkyl chains on positions 7 and 8, were synthesized in the attempt to obtain potent and selective antagonists for the A(2A) adenosine receptor subtype. The compounds were tested in binding and functional assays to evaluate their potency for the A(2A) compared with the A(1) adenosine receptor subtype. In binding studies in rat brain membranes, most of the compounds showed affinity for A(2A) receptors in the low nanomolar range with a different degree of A(2A) versus A(1) selectivity. Comparison of N-7 (10a-d,h-o)- and N-8 (10e-g)-substituted pyrazolo derivatives indicates that N-7 substitution decreases the A(1) affinity with the concomitant increase of A(2A) selectivity. Specifically, the introduction of a 3-phenylpropyl group at pyrazolo nitrogen in position 7 (101) increased significantly the A(2A) selectivity, being 210-fold, while the A(2A) receptor affinity remained high (K-i = 2.4 nM). With regards to the affinity for A(2A) receptors, also the compound 10n, bearing in the 7-position a beta-morpholin-4-ylethyl group, deserves attention (K-i = 5.6 nM) even though the A(2A) selectivity (84-fold) was not as high as that of 101. Conversely, the compound 10m (N-7-4-phenylbutyl derivative) showed a remarkable selectivity (A(1)/A(2A) ratio = 129) associated with lower A(2A) affinity (K-i = 21 nM). In functional studies, most of the compounds examined reversed 5'-(N-ethylcarbamoyl)adenosine-induced inhibition of rabbit platelet aggregation inhibition which is a biological response mediated by the A(2A) receptor subtype. The compounds are potent and selective A(2A) antagonists which can be useful to elucidate the pathophysiological role of this adenosine receptor subtype. These compounds deserve to be further developed to assess their potential for treatment of neurodegenerative disorders such as Parkinson's disease.

  DOI：

  10.1021/jm950746l
• 作为产物：
  描述：

  3-氨基-4-氰基吡唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-Butyl-5-amino-4-cyan-pyrazol 、 1-butyl-4-cyano-3-aminopyrazole
  参考文献：
  名称：

  Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine Derivatives:  Potent and Selective A_2A Adenosine Antagonists

  摘要：

  A series of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives (10a-o,q,r), bearing alkyl and aralkyl chains on positions 7 and 8, were synthesized in the attempt to obtain potent and selective antagonists for the A(2A) adenosine receptor subtype. The compounds were tested in binding and functional assays to evaluate their potency for the A(2A) compared with the A(1) adenosine receptor subtype. In binding studies in rat brain membranes, most of the compounds showed affinity for A(2A) receptors in the low nanomolar range with a different degree of A(2A) versus A(1) selectivity. Comparison of N-7 (10a-d,h-o)- and N-8 (10e-g)-substituted pyrazolo derivatives indicates that N-7 substitution decreases the A(1) affinity with the concomitant increase of A(2A) selectivity. Specifically, the introduction of a 3-phenylpropyl group at pyrazolo nitrogen in position 7 (101) increased significantly the A(2A) selectivity, being 210-fold, while the A(2A) receptor affinity remained high (K-i = 2.4 nM). With regards to the affinity for A(2A) receptors, also the compound 10n, bearing in the 7-position a beta-morpholin-4-ylethyl group, deserves attention (K-i = 5.6 nM) even though the A(2A) selectivity (84-fold) was not as high as that of 101. Conversely, the compound 10m (N-7-4-phenylbutyl derivative) showed a remarkable selectivity (A(1)/A(2A) ratio = 129) associated with lower A(2A) affinity (K-i = 21 nM). In functional studies, most of the compounds examined reversed 5'-(N-ethylcarbamoyl)adenosine-induced inhibition of rabbit platelet aggregation inhibition which is a biological response mediated by the A(2A) receptor subtype. The compounds are potent and selective A(2A) antagonists which can be useful to elucidate the pathophysiological role of this adenosine receptor subtype. These compounds deserve to be further developed to assess their potential for treatment of neurodegenerative disorders such as Parkinson's disease.

  DOI：

  10.1021/jm950746l

文献信息

• A Facile One-pot Synthesis of 1-Arylpyrazolo[3,4-d]Pyrimidin- 4-ones
  作者：Xiaohong Zhang、Qiulian Lin、Ping Zhong

  DOI：10.3390/molecules15053079

  日期：——

  One pot synthesis of 1-arylpyrazolo[3,4-d]pyrimidin-4-ones by the reaction of 5-amino-N-substituted-1H-pyrazole-4-carbonitrile with different lower aliphatic acids in the presence of POCl3has been developed. The structures of all the title compounds have been confirmed by IR, 1H-NMR, 13C-NMR, and elemental analyses. Moreover, the structures of one of these compounds, 2c, was confirmed by single-crystal X-ray diffraction.

  一锅法合成1-芳基吡唑并[3,4-d]嘧啶-4-酮类化合物，通过5-氨基-N-取代-1H-吡唑-4-氰与不同低级脂肪酸在POCl3存在下的反应实现。所有目标化合物的结构已通过IR、1H-NMR、13C-NMR及元素分析确认。此外，其中一种化合物2c的结构还通过单晶X射线衍射进一步确认。
• Adenosine A3 receptor modulators
  申请人：——

  公开号：US20030144266A1

  公开（公告）日：2003-07-31

  The compounds of the following formula: 1 wherein R, R 2 , R 3 and A have the meanings given in the specification, are endowed with selective A 3 adenosine receptor antagonist activity. These compounds can be used in a pharmaceutical composition to treat disorders caused by excessive activation of the A 3 receptor, or can be used in a diagnostic application to determine the relative binding of other compounds to the A 3 receptor. The compounds can be labeled, for example with fluorescent or radiolabels, and the labels used in vivo or in vitro to determine the presence of tumor cells which possess a high concentration of adenosine A 3 receptors.

  具有以下公式的化合物：其中R、R2、R3和A具有规范中给定的含义，具有选择性A3腺苷受体拮抗活性。这些化合物可以用于制备药物组合物，用于治疗由A3受体过度激活引起的疾病，也可以用于诊断应用，以确定其他化合物与A3受体的相对结合。这些化合物可以被标记，例如用荧光标记或放射性标记，并且这些标记可以在体内或体外用于确定具有高浓度腺苷A3受体的肿瘤细胞的存在。
• ADENOSINE A3 RECEPTOR MODULATORS
  申请人：Baraldi Giovanni Pier

  公开号：US20070249641A1

  公开（公告）日：2007-10-25

  The compounds of the following formula: wherein R, R 2 , R 3 and A have the meanings given in the specification, are endowed with selective A 3 adenosine receptor antagonist activity. These compounds can be used in a pharmaceutical composition to treat disorders caused by excessive activation of the A 3 receptor, or can be used in a diagnostic application to determine the relative binding of other compounds to the A 3 receptor. The compounds can be labeled, for example with fluorescent or radiolabels, and the labels used in vivo or in vitro to determine the presence of tumor cells which possess a high concentration of adenosine A 3 receptors.

  以下化学式的化合物：其中R、R2、R3和A在说明书中给出的含义，具有选择性A3腺苷受体拮抗活性。这些化合物可以用于制备药物组合物，用于治疗由A3受体过度激活引起的疾病，或者可以用于诊断应用，以确定其他化合物与A3受体的相对结合。这些化合物可以被标记，例如用荧光或放射性标记，并在体内或体外用于确定具有高浓度腺苷A3受体的肿瘤细胞的存在。
• Pyrazolopyrimidine derivatives as BTK inhibitors for the treatment of cancer
  申请人：Loxo Oncology, Inc.

  公开号：US10399989B2

  公开（公告）日：2019-09-03

  This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK). The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.

  本发明涉及新型化合物。本发明的化合物是酪氨酸激酶抑制剂。具体来说，本发明的化合物可用作布鲁顿酪氨酸激酶（BTK）的抑制剂。本发明还考虑将这些化合物用于治疗可通过抑制布鲁顿酪氨酸激酶治疗的疾病，例如癌症、淋巴瘤、白血病和免疫性疾病。
• US6407236B1
  申请人：——

  公开号：US6407236B1

  公开（公告）日：2002-06-18