2-(2'-hydroxyethylamino)-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine

• 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'-hydroxyethylamino)-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine
• 英文别名: tubulizine；2-[[4,6-Bis[(4-methoxyphenyl)methylamino]-1,3,5-triazin-2-yl]amino]ethanol
• 化学式: C₂₁H₂₆N₆O₃
• 分子量: 410.476
• InChiKey: PDNBUYQRCGHOEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2'-hydroxyethylamino)-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine 在 4-二甲氨基吡啶 、 magnesium ascorbate 、 copper(II) sulfate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 4-{5'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-5'-oxopentyl}-1-{3'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-3'-oxopropyl}-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：

  4-甲氧基苄胺 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 80.33h， 生成 2-(2'-hydroxyethylamino)-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

文献信息

• A Novel Microtubule Destabilizing Entity from Orthogonal Synthesis of Triazine Library and Zebrafish Embryo Screening
  作者：Ho-Sang Moon、Eric M. Jacobson、Sonya M. Khersonsky、Michael R. Luzung、Daniel P. Walsh、Wennan Xiong、Jae Wook Lee、Puja B. Parikh、Jennifer C. Lam、Tae-Wook Kang、Gustavo R. Rosania、Alexander F. Schier、Young-Tae Chang

  DOI：10.1021/ja026720i

  日期：2002.10.1

  The first orthogonal combinatorial synthesis of a high-purity triazine library was demonstrated. Novel triazine-based microtubule inhibitors were discovered by an efficient zebrafish embryo screening and in vitro microtubule polymerization assay.
• Exploiting fluorescein based drug conjugates for fluorescent monitoring in drug delivery
  作者：Andrii Bazylevich、Leonid D. Patsenker、Gary Gellerman

  DOI：10.1016/j.dyepig.2016.11.057

  日期：2017.4

  Anticancer drugs connected to fluorescein based chemosensors by different biodegradable linkers were investigated for fluorescent monitoring in drug delivery models. The drug release triggered by chemo- and bio-hydrolytic environments was visualized on the basis of "switch on" fluorescence of the fluorophore moiety of fluorescein-drug conjugates. The conjugation of free phenolic hydroxyl of fluorescein chemosensor to the hydroxyl group of the drugs was employed by biodegradable oxy- and amino acrylate linkers. The chemosensor also possesses a free carboxylic group for potential conjugation to a specific carrier for targeted drug delivery applications. Fluorescent monitoring of drug release, quantum yield and other spectroscopic characteristics of our novel fluorescein-drug conjugates were measured and discussed. The work offers a versatile fluorophore platform for the fluorescent observation of drug delivery. (C) 2016 Elsevier Ltd. All rights reserved.
• 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.