2-chloro-4,6-di(4-methoxybenzylamino)-1,3,5-triazine | 210992-90-8

• 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-chloro-4,6-di(4-methoxybenzylamino)-1,3,5-triazine
• 英文别名: 6-chloro-2-N,4-N-bis[(4-methoxyphenyl)methyl]-1,3,5-triazine-2,4-diamine
• CAS: 210992-90-8
• 化学式: C₁₉H₂₀ClN₅O₂
• 分子量: 385.853
• InChiKey: BOFIFDGNXQOWOG-UHFFFAOYSA-N

物化性质

• 沸点：
  616.6±65.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-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 、 1,4-二氧六环 、 水 为溶剂， 反应 108.0h， 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：

  三聚氯氰 、 4-甲氧基苄胺 在 sodium hydroxide 作用下， 以 丙酮 、 水 为溶剂， 反应 20.33h， 以92%的产率得到2-chloro-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

• Solid phase synthesis of novel biaryl triazine library by suzuki cross coupling
  申请人：NEW YORK UNIVERSITY

  公开号：US20040225125A1

  公开（公告）日：2004-11-11

  Two methods are used to produce diaryl trisubstituted triazines. In the first method, cyanuric chloride is first reacted with a 4-alkoxybenzylamine. The product of this reaction is then reacted with a resin-bound amine, such as 4-alkoxybenzylamine, to ensure that the final compound will be bound to a resin. The product of this reaction is then reacted with boronic acid to produce a trisubstituted diaryl triazine. In the second method, cyanuric chloride is reacted with a benzenealkanethiol. The product of this reaction is then reacted with a resin-bound amine, such as 4-alkoxybenzylamine, to ensure that the final compound will be bound to a resin. The product of this reaction is then reacted with m-CPBA to form a sulfone, which is then reacted with a 4-alkoxybenzylamine to form the desired trisubstituted biaryltriazine.

  有两种方法可以制备二苯基三取代三嗪。第一种方法是，首先将氰尿酸氯与4-烷氧基苯甲胺反应。然后将该反应产物与树脂结合胺（如4-烷氧基苯甲胺）反应，以确保最终化合物与树脂结合。然后将该反应产物与硼酸反应，以产生三取代二苯基三嗪。第二种方法是，将氰尿酸氯与苯基烷硫醇反应。然后将该反应产物与树脂结合胺（如4-烷氧基苯甲胺）反应，以确保最终化合物与树脂结合。然后将该反应产物与m-CPBA反应形成烷基磺酰，然后再与4-烷氧基苯甲胺反应形成所需的三取代联苯三嗪。
• PYRAZOLE DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1022270A1

  公开（公告）日：2000-07-26

  A compound represented by formula (I) or a salt thereof; wherein R1 and R2, which may be the same or different, each represent a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an amino group, an alkylamino group, an aryl group or an alkyl group; R3 and R4, which may be the same, or different, each represent a hydrogen atom, a halogen atom, an alkoxy group, an amino group, an alkylamino group, an aryl group or an alkyl group; R5 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or an arylalkyl group; Q represents an amidino group, a cycloalkyl group, a phenyl group or amonocyclic heterocyclic group except a pyrimidinyl group bonded to the N atom at its 2-position; G represents a nitrogen-containing saturated heterocyclic structure represented by formula: wherein X1 represents a nitrogen atom or CH, in which the ring may have a keto group and may have one or more substituents; Z represents a phenyl or heterocyclic group which may have one or more substituents, in which two substituents on the phenyl or heterocyclic group may be connected to each other to form a ring to provide a condensed bicyclic structure as a whole; the substituent on Z and the substituent on G may be connected to each other to form a condensed tricyclic or tetracyclic structure as a whole, and an antitumor agent containing the compound or a salt thereof as an active ingredient.

  式 (I) 所代表的化合物或其盐； 其中 R1 和 R2 可以相同或不同，各自代表氢原子、卤素原子、羟基、烷氧基、氨基、烷基氨基、芳基或烷基； R3 和 R4 可以相同或不同，各自代表氢原子、卤素原子、烷氧基、氨基、烷基氨基、芳基或烷基；R5 代表氢原子、烷基、烯基、炔基、芳基或芳烷基； Q 代表脒基、环烷基、苯基或胺环杂环基团，但在 2 位与 N 原子键合的嘧啶基除外； G 代表由式表示的含氮饱和杂环结构： 其中 X1 代表氮原子或 CH、 其中环可具有酮基，并可具有一个或多个取代基； Z代表苯基或杂环基团，可具有一个或多个取代基，其中苯基或杂环基团上的两个取代基可相互连接形成一个环，以提供一个整体的缩合双环结构；Z上的取代基和G上的取代基可以相互连接，形成一个缩合的三环或四环结构整体，以及含有该化合物或其盐作为活性成分的抗肿瘤剂。
• US6169086
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Identification of 12Cysβ on tubulin as the binding site of tubulyzine
  作者：Yeoun Jin Kim、Dan L. Sackett、Matthieu Schapira、Daniel P. Walsh、Jaeki Min、Lewis K. Pannell、Young-Tae Chang

  DOI：10.1016/j.bmc.2005.09.069

  日期：2006.2

  We have Undertaken quantitative binding site studies in order to identify the binding site of the known microtubule destabilizing agents, the tubulyzines, in the tubulin dimer. Two different approaches were employed that utilized the tubulyzines and their derivatives. The first approach was based on a chemical affinity labeling method using tubulyzine affinity derivatives, and the second approach employed the mass spectrometric measurement of the differential reactivity of cysteines using the tubulyzines and monobromobimane. Based oil overlapping data from these two approaches, we propose that the tubulyzines bind at the guanosine-5'-triphosphate binding site of beta-tubulin. Interestingly, we also show that the tubulyzines' binding to tubulin induces a conformational Change in tubulin that prevents further interaction of the 239Cys beta with other reagents. (c) 2005 Elsevier Ltd. All rights reserved.