2-[2'-(5-hexynoyloxy)ethylamino]-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine | 1391054-29-7

• 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: 2-[2'-(5-hexynoyloxy)ethylamino]-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine
• CAS: 1391054-29-7
• 化学式: C₂₇H₃₂N₆O₄
• 分子量: 504.589
• InChiKey: OBWGWEYOCMTJFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  37.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119.52
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(6-azidocaproyl)deacetylcolchicine 、 2-[2'-(5-hexynoyloxy)ethylamino]-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine 在 magnesium ascorbate 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以73%的产率得到4-{4'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-4'-oxobutyl}-1-{6'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-6'-oxohexyl}-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel anticancer bivalent colchicine–tubulizine hybrids

  摘要：

  A series of novel antimitotic hybrids were synthesized in good yields by linking of azide-containing colchicine congeners with acetylene-substituted tubulizine-type derivatives using copper-mediated 1,3-dipolar cycloaddition. Obtained compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50 = 0.599-2.93 mu M). Several newly synthesized compounds are the substoichiometric inhibitors of microtubule assembly (R = 0.41-0.78). The results highlight the importance of the length of spacer linking the tubulin binding ligands in heterodimeric molecules. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.072
• 作为产物：
  描述：

  2-chloro-4,6-di(4-methoxybenzylamino)-1,3,5-triazine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 84.0h， 生成 2-[2'-(5-hexynoyloxy)ethylamino]-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel anticancer bivalent colchicine–tubulizine hybrids

  摘要：

  A series of novel antimitotic hybrids were synthesized in good yields by linking of azide-containing colchicine congeners with acetylene-substituted tubulizine-type derivatives using copper-mediated 1,3-dipolar cycloaddition. Obtained compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50 = 0.599-2.93 mu M). Several newly synthesized compounds are the substoichiometric inhibitors of microtubule assembly (R = 0.41-0.78). The results highlight the importance of the length of spacer linking the tubulin binding ligands in heterodimeric molecules. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.072