4-Amino-3-benzylpyrazolo<3,4-d>pyrimidine | 42754-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 4-Amino-3-benzylpyrazolo<3,4-d>pyrimidine
• 英文别名: 3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine；3-benzyl-1(2)H-pyrazolo[3,4-d]pyrimidin-4-ylamine；4-Amino-3-benzyl-pyrazolo<3,4-d>pyrimidin；3-Benzyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine；3-benzyl-2H-pyrazolo[3,4-d]pyrimidin-4-amine
• CAS: 42754-71-2
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: VZPNMLSEFMQFDU-UHFFFAOYSA-N

物化性质

• 熔点：
  277 °C(Solv: methanol (67-56-1))
• 沸点：
  377.3±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Amino-3-benzylpyrazolo<3,4-d>pyrimidine 在 葡萄糖 、 氨 、 四氯化锡 、 hexokinase 、 三氯氧磷 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 41.71h， 生成 (2S,3R,4S,5R)-2-(4-amino-3-benzylpyrazolo[3,4-d]pyrimidin-1-yl)-5-hydroxymethyltetrahydrofuran-3,4-diol-5'-diphosphate
  参考文献：
  名称：

  Inhibitor Scaffolds as New Allele Specific Kinase Substrates

  摘要：

  The elucidation of protein kinase signaling networks is challenging due to the large size of the protein kinase superfamily (> 500 human kinases). Here we describe a new class of orthogonal triphosphate substrate analogues for the direct labeling of analogue-specific kinase protein targets. These analogues were constructed as derivatives of the Src family kinase inhibitor PP1 and were designed based on the crystal structures of PP1 bound to HCK and N-6-(benzyl)-ADP bound to c-Src (T338G). 3-Benzylpyrazolopyrimidine triphosphate (3-benzyl-PPTP) proved to be a substrate for a mutant of the MAP kinase p38 (p38-T106G/A157L/L167A). 3-Benzyl-PPTP was preferred by v-Src (T338G) (k(cat)/K-M = 3.2 x 10(6) min(-1) M-1) over ATP or the previously described ATP analogue, N-6 (benzyl) ATP. For the kinase CDK2 (F80G)/cyclin E, 3-benzyl-PPTP demonstrated catalytic efficiency (k(cat)/K-M = 2.6 x 10(4) min(-1) M-1) comparable to ATP (k(cat)/K-M = 5.0 x 10(4) min(-1) M-1) largely due to a significantly better K-M (6.4 muM vs 530 muM). In kinase protein substrate labeling experiments both 3-benzyl-PPTP and 3-phenyl-PPTP prove to be over 4 times more orthogonal than N-6-(benzyl)-ATP with respect to the wild-type kinases found in murine spleenocyte cell lysates. These experiments also demonstrate that [gamma-P-32]-3-benzyl-PPTP is an excellent phosphodonor for labeling the direct protein substrates of CDK2 (F80G)/E in murine spleenocyte cell lysates, even while competing with cellular levels (4 mM) of unlabeled ATP. The fact that this new more highly orthogonal nucleotide is accepted by three widely divergent kinases studied here suggests that it is likely to be generalizable across the entire kinase superfamily.

  DOI：

  10.1021/ja0264798
• 作为产物：
  描述：

  1-(4-吗啉)-2-苯基乙烷硫酮 在 potassium carbonate 、 一水合肼 、 二甲基亚砜 作用下， 反应 0.5h， 生成 4-Amino-3-benzylpyrazolo<3,4-d>pyrimidine
  参考文献：
  名称：

  Tominaga, Yoshinori; Matsuoka, Yoshiki; Oniyama, Yukio, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 647 - 660

  摘要：

  DOI：

文献信息

• TOMINAGA, YOSHINORI;MATSUOKA, YOSHIKI;ONIYAMA, YUKIO;UCHIMURA, YOSHIMITSU+, J. HETEROCYCL. CHEM., 27,(1990) N, C. 647-660
  作者：TOMINAGA, YOSHINORI、MATSUOKA, YOSHIKI、ONIYAMA, YUKIO、UCHIMURA, YOSHIMITSU+

  DOI：——

  日期：——
• ANTI-INFLAMMATORY PYRAZOLOPYRIMIDINES
  申请人：Shokat Kevan M.

  公开号：US20090124638A1

  公开（公告）日：2009-05-14

  The present invention provides anti-inflammatory compounds useful in the treatment of diseases and conditions in which inflammation is involved in disease progression or the manifestation of symptoms of the disease or condition.
• Anti-Inflammatory Pyrazolopyrimndines
  申请人：Shokat Kevan M.

  公开号：US20110144134A1

  公开（公告）日：2011-06-16

  The present invention provides anti-inflammatory compounds useful in the treatment of diseases and conditions in which inflammation is involved in disease progression or the manifestation of symptoms of the disease or condition.
• US9512125B2
  申请人：——

  公开号：US9512125B2

  公开（公告）日：2016-12-06