4-bromomethyl-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazolyl)-1,3,5-triazin-2-amine | 334993-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 4-bromomethyl-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazolyl)-1,3,5-triazin-2-amine
• 英文别名: 2-amino-4-(3,3,5-trimethylpyrazolin-2-yl)-6-(1-bromomethyl)-1,3,5-triazine；4-(bromomethyl)-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazol-1-yl)-1,3,5-triazin-2-amine；4-(bromomethyl)-6-(3,5,5-trimethyl-4H-pyrazol-1-yl)-1,3,5-triazin-2-amine
• CAS: 334993-82-7
• 化学式: C₁₀H₁₅BrN₆
• 分子量: 299.173
• InChiKey: RWPOJZGGDICCEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-bromomethyl-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazolyl)-1,3,5-triazin-2-amine 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 dimethyl {4-[{[2-amino-4-(3,5,5-trimethylpyrazolin-2-yl)-1,3,5-triazin-6-yl]methyl}methylamino]benzoyl}-L-aspartate
  参考文献：
  名称：

  Saczewski; Bulakowska, Polish Journal of Chemistry, 2005, vol. 79, # 4, p. 739 - 748

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙酸乙酯 、 N-(二氨基亚甲基)-3,5,5-三甲基-4H-吡唑-1-甲脒 以 甲醇 为溶剂， 反应 2.5h， 以26%的产率得到4-bromomethyl-6-(3,5,5-trimethyl-4,5-dihydro-1H-pyrazolyl)-1,3,5-triazin-2-amine
  参考文献：
  名称：

  Saczewski; Bulakowska, Polish Journal of Chemistry, 2005, vol. 79, # 4, p. 739 - 748

  摘要：

  DOI：

文献信息

• Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives
  作者：Z. Brzozowski、F. Sączewski、M. Gdaniec

  DOI：10.1016/s0223-5234(00)01194-6

  日期：2000.12

  The syntheses, structural elucidation based on NMR spectroscopy and X-ray analysis of 8 as well as antitumor activities of novel 2,4-diamino-1,3,5-triazine derivatives 5 and 7-22 are described. Screenings performed at NCI showed that most derivatives possessed a moderate to strong growth inhibition activity on various tumor panel cell lines between 0.148 and 56.2 microM concentrations. 2-Amino-6-bromomethyl-4-(3

  描述了合成，基于NMR的结构解析和8的X射线分析以及新型2,4-二氨基-1,3,5-三嗪衍生物5和7-22的抗肿瘤活性。在NCI上进行的筛选显示，大多数衍生物在0.148-56.2 microM浓度的各种肿瘤细胞系上具有中等至强的生长抑制活性。2-Amino-6-bromomethyl-4-（3,5,5-trimethyl-2-pyrazoline）-1,3,5-triazine 11显示出最有效的抗肿瘤活性，其平均中点值为log（10）GI50，所有测试的log（10）TGI50和log（10）LC50分别等于-5.26，-4.81和-4.37，因此，可以将其视为抗癌剂进一步开发的先导结构。
• Synthesis, structure and anticancer activity of novel alkenyl-1,3,5-triazine derivatives
  作者：F. Sączewski、A. Bułakowska

  DOI：10.1016/j.ejmech.2005.12.012

  日期：2006.5

  A series of novel 4-(E)-ethenyl-6-alkylamino-1,3,5-triazin-2-ylamine derivatives 9-17 have been synthesized by a Wittig reaction of corresponding alkyltriphenylphosphonium bromides 5-8 with (hetero)aromatic aldehydes. The E configuration of these alkenes was confirmed by I H NMR spectroscopic data. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activity against a panel of 56 tumor cell lines and relationship between structure and in vitro antitumor activity is discussed. The most active compounds 14 and 17 showed 50% growth inhibitory activity in low micromolar concentrations against renal cancer A498 cell line and colon cancer cell line COLO 205, respectively. (c) 2006 Elsevier SAS. All rights reserved.
• 2-Amino-6-(1-imidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-1,3,5-triazine and 2-amino-6-(1-benzimidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-1,3,5-triazine hemihydrate
  作者：Maria Gdaniec、Franciszek Sączewski、Zdzisław Brzozowski

  DOI：10.1107/s0108270103025058

  日期：2003.12.15

  The two title compounds, C13H18N8 and C17H20N8.0.5H(2)O, possess similar molecular shapes, with the pyrazoline moiety and s-triazine ring located approximately in one plane, and the imidazole or benzimidazole ring nearly perpendicular to the s-triazine nucleus. In both crystal structures, despite there being a large number of accessible hydrogen-bond acceptor sites, only one H atom from the NH2 group is involved in hydrogen bonding; the molecules are assembled into discrete centrosymmetric dimers via a pair of nearly linear N-H...N hydrogen bonds.