1-(2-azidoethyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine | 1286278-44-1

• 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-(2-azidoethyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• 英文别名: 1-(2-azidoethyl)-3-phenylpyrazolo[3,4-d]pyrimidin-4-amine
• CAS: 1286278-44-1
• 化学式: C₁₃H₁₂N₈
• 分子量: 280.292
• InChiKey: QQDFGUQQJRMDKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-azidoethyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 、 4-乙炔基苯乙酮 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(4-(1-(2-(4-amino-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)phenyl)ethanone
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

  摘要：

  A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 mu M. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.047
• 作为产物：
  描述：

  α-cyano-β-hydroxycinnamonitrile 在 吡啶 、 sodium azide 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 1-(2-azidoethyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

  摘要：

  A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 mu M. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.047

文献信息

• Development of the phenylpyrazolo[3,4-<i>d</i>]pyrimidine-based, insulin-like growth factor receptor/Src/AXL-targeting small molecule kinase inhibitor
  作者：Ho Jin Lee、Phuong Chi Pham、Honglan Pei、Bumhee Lim、Seung Yeob Hyun、Byungyeob Baek、Byungjin Kim、Yunha Kim、Min-Hwan Kim、Nae-Won Kang、Hye-Young Min、Dae-Duk Kim、Jeeyeon Lee、Ho-Young Lee

  DOI：10.7150/thno.48865

  日期：——

  Rationale: The type I insulin-like growth factor receptor (IGF-1R) signaling pathway plays key roles in the development and progression of numerous types of human cancers, and Src and AXL have been found to confer resistance to anti-IGF-1R therapies. Hence, co-targeting Src and AXL may be an effective strategy to overcome resistance to anti-IGF-1R therapies. However, pharmacologic targeting of these three kinases may result in enhanced toxicity. Therefore, the development of novel multitarget anticancer drugs that block IGF-1R, Src, and AXL is urgently needed.

  理由：I型胰岛素样生长因子受体（IGF-1R）信号通路在多种类型人类癌症的发生和发展过程中发挥着关键作用，而Src和AXL已被发现会产生抗IGF-1R疗法的耐药性。因此，联合靶向Src和AXL可能是克服抗IGF-1R疗法耐药性的有效策略。然而，药物靶向这三种激酶可能会导致毒性增强。因此，亟需开发能阻断 IGF-1R、Src 和 AXL 的新型多靶点抗癌药物。
• Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities
  作者：Anil Kumar、Israr Ahmad、Bhupender S. Chhikara、Rakesh Tiwari、Deendayal Mandal、Keykavous Parang

  DOI：10.1016/j.bmcl.2011.01.047

  日期：2011.3

  A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 mu M. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 mu M. (C) 2011 Elsevier Ltd. All rights reserved.