4-{4'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-4'-oxobutyl}-1-{10'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-10'-oxodecanyl}-1,2,3-triazole | 1391054-47-9

• 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-{4'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-4'-oxobutyl}-1-{10'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-10'-oxodecanyl}-1,2,3-triazole
• 英文别名: 2-[[4,6-bis[(4-methoxyphenyl)methylamino]-1,3,5-triazin-2-yl]amino]ethyl 4-[1-[10-oxo-10-[[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]decyl]triazol-4-yl]butanoate
• CAS: 1391054-47-9
• 化学式: C₅₇H₇₂N₁₀O₁₀
• 分子量: 1057.26
• InChiKey: DHRFUCHMSFDUBS-DXQCBLCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  77
• 可旋转键数：
  32
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  233
• 氢给体数：
  4
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  秋水仙碱 在 4-二甲氨基吡啶 、 magnesium ascorbate 、 sodium methylate 、 copper(II) sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 37.5h， 生成 4-{4'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-4'-oxobutyl}-1-{10'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-10'-oxodecanyl}-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

文献信息

• Synthesis and biological evaluation of novel anticancer bivalent colchicine–tubulizine hybrids
  作者：Yulia B. Malysheva、Sebastien Combes、Diane Allegro、Vincent Peyrot、Paul Knochel、Andrei E. Gavryushin、Alexey Yu. Fedorov

  DOI：10.1016/j.bmc.2012.05.072

  日期：2012.7

  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.