3-methyl-1-(quinolin-2-yl)-1H-pyrazolo[3,4-d]pyrimidine | 1410783-62-8

• 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: 3-methyl-1-(quinolin-2-yl)-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 2-(3-Methylpyrazolo[3,4-d]pyrimidin-1-yl)quinoline；2-(3-methylpyrazolo[3,4-d]pyrimidin-1-yl)quinoline
• CAS: 1410783-62-8
• 化学式: C₁₅H₁₁N₅
• 分子量: 261.286
• InChiKey: BLXCZCSIWACIJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-Methyl-2-quinolin-2-ylpyrazol-3-amine 、 formamide 在 三溴化磷 作用下， 以84%的产率得到3-methyl-1-(quinolin-2-yl)-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  One-pot synthesis and antiproliferative evaluation of pyrazolo[3,4-d]pyrimidine derivatives

  摘要：

  An efficient one-pot methodology for the synthesis of pyrazolo[3,4-d]pyrimidines was developed by using 5-aminopyrazoles with formamide in presence of PBr3 as the coupling agent. Among the examples presented in this work, compounds 41 and 54-56 with phenyl or 2-quinolinyl groups at N-1 and p-Me-Ph, p-Cl-Ph, or p-OMe-Ph group at C-3 position in the pyrazole ring possessed better potency against NCl-H226 and NPC-TW01 cancer cells with GI(50) values between 18 mu M and 39 mu M. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.054

文献信息

• One-pot synthesis and antiproliferative evaluation of pyrazolo[3,4-d]pyrimidine derivatives
  作者：Yu-Ying Huang、Li-Ya Wang、Chun-Hsi Chang、Yueh-Hsiung Kuo、Kimiyoshi Kaneko、Hiroyuki Takayama、Masayuki Kimura、Shin-Hun Juang、Fung Fuh Wong

  DOI：10.1016/j.tet.2012.09.054

  日期：2012.11

  An efficient one-pot methodology for the synthesis of pyrazolo[3,4-d]pyrimidines was developed by using 5-aminopyrazoles with formamide in presence of PBr3 as the coupling agent. Among the examples presented in this work, compounds 41 and 54-56 with phenyl or 2-quinolinyl groups at N-1 and p-Me-Ph, p-Cl-Ph, or p-OMe-Ph group at C-3 position in the pyrazole ring possessed better potency against NCl-H226 and NPC-TW01 cancer cells with GI(50) values between 18 mu M and 39 mu M. (c) 2012 Elsevier Ltd. All rights reserved.