6-(chloromethyl)-N²-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine | 99860-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(chloromethyl)-N²-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine
• 英文别名: 6-chloromethyl-N-(4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine；2-Amino-6-chlormethyl-4-p-anisidino-triazin-<1.3.5>；4-Chlormethyl-6-(p-methoxy-phenylamino)-2-amino-symm.-triazin；6-(chloromethyl)-N2-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine；6-(chloromethyl)-2-N-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine
• CAS: 99860-38-5
• 化学式: C₁₁H₁₂ClN₅O
• mdl: MFCD03941305
• 分子量: 265.702
• InChiKey: WNMJRAUNFFYVKN-UHFFFAOYSA-N

物化性质

• 沸点：
  508.4±60.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)
• 溶解度：
  >39.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  86
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[4-bromobenzylideneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol 、 6-(chloromethyl)-N²-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以79%的产率得到6-{[4-(4-bromobenzylideneamino)-5-phenyl-4H-1,2,4-triazol-3-ylthio]methyl}-N2-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Synthesis and antiviral activity of benzimidazolyl- and triazolyl-1,3,5-triazines

  摘要：

  A novel series of 1,3,5-triazine analogs was successfully synthesized through conjugation with benzimidazole or 1,2,4-triazole derivatives via a methylenethio linker. The new analogs were in vitro evaluated against HSV-1 in Vero cells; among these analogs, two compounds exhibited good effect in inhibiting HSV-1 replication (for compound 5p: EC50 = 3.5 mu g/ml, SI = 358; for compound 5r: EC50 = 5.0 mu g/ml, SI = 300) in comparison to acyclovir.

  DOI：

  10.1007/s00044-011-9574-8
• 作为产物：
  描述：

  甲氧苯胺 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 51.0h， 生成 6-(chloromethyl)-N²-(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Synthesis and antiviral activity of benzimidazolyl- and triazolyl-1,3,5-triazines

  摘要：

  A novel series of 1,3,5-triazine analogs was successfully synthesized through conjugation with benzimidazole or 1,2,4-triazole derivatives via a methylenethio linker. The new analogs were in vitro evaluated against HSV-1 in Vero cells; among these analogs, two compounds exhibited good effect in inhibiting HSV-1 replication (for compound 5p: EC50 = 3.5 mu g/ml, SI = 358; for compound 5r: EC50 = 5.0 mu g/ml, SI = 300) in comparison to acyclovir.

  DOI：

  10.1007/s00044-011-9574-8

文献信息

• Identifying Lysophosphatidic Acid Acyltransferase β (LPAAT-β) as the Target of a Nanomolar Angiogenesis Inhibitor from a Phenotypic Screen Using the Polypharmacology Browser PPB2
  作者：Marion Poirier、Mahendra Awale、Matthias A. Roelli、Guy T. Giuffredi、Lars Ruddigkeit、Lasse Evensen、Amandine Stooss、Serafina Calarco、James B. Lorens、Roch-Philippe Charles、Jean-Louis Reymond

  DOI：10.1002/cmdc.201800554

  日期：2019.1.22

  which suggested lysophosphatidic acid acyltransferase β (LPAAT-β) as a possible target for this aminotriazine as well as several analogues identified by structure-activity relationship profiling. LPAAT-β inhibition (IC50 ≈15 nm) was confirmed in a biochemical assay and by its effects on cell proliferation in comparison with a known LPAAT-β inhibitor. These experiments illustrate the value of target-prediction

  通过在表型共培养测定中筛选激酶抑制剂类似物的聚焦库以抑制血管生成，我们确定了一种氨基三嗪，它可作为一种抑制细胞生长的纳摩尔抑制剂。但是，发现该氨基三嗪在全基因组谱分析中完全没有活性。为了解释其作用机理，我们使用了在线靶标预测工具PPB2（http://ppb2.gdb.tools），该工具建议溶血磷脂酸酰基转移酶β（LPAAT-β）作为该氨基三嗪和其他类似物的可能靶标。通过结构-活动关系分析来识别。与已知的LPAAT-β抑制剂相比，在生化分析中证实了LPAAT-β抑制（IC50≈15 nm），并且抑制了它对细胞增殖的作用。
• Arylbiguanides in Heterocyclization Reactions
  作者：D. V. Kryl’skii、Kh. S. Shikhaliev、A. S. Shestakov、M. M. Liberman

  DOI：10.1007/s11176-005-0218-x

  日期：2005.2

  The reactions of arylbiguanides with acetyacetone derivatives were used to obtain N-(pyrimidin-2-yl)-N′-arylguanidines, and the reactions with acetoacetic ester derivatives (depending on the structure of the keto esters), N-aryl-N′-(4-oxo-3,4-dihydropyrimidin-2-yl)guanidines or 2-amino-4-arylamino-6-aryl(heteryl)-sulfanylmethylene-1,3,5-triazines. The N-aryl-N′-heterylguanidines formed by the reactions with anhydrides, acyl halides, and aryl isocyanates give rise to the corresponding triaza derivatives.

  芳基双胍与乙酰丙酮衍生物反应得到N-(嘧啶-2-基)-N'-芳基胍，与乙酰乙酸酯衍生物(取决于酮酯的结构)、N-芳基-N'反应-(4-氧代-3,4-二氢嘧啶-2-基)胍或2-氨基-4-芳基氨基-6-芳基(杂基)-硫酰亚甲基-1,3,5-三嗪。通过与酸酐、酰卤和芳基异氰酸酯反应形成的N-芳基-N'-杂基胍产生相应的三氮杂衍生物。
• Synthesis of 2-amino-4-arylamino-6-benzo[b]furan-2-yl-1,3,5-triazines
  作者：Kh. S. Shikhaliev、M. M. Liberman、D. V. Kryl’skii

  DOI：10.1007/s11172-005-0207-6

  日期：2004.12

  The alkylation of salicylaldehyde and o-hydroxyacetophenone with 2-amino-4-arylamino-6-chloromethyl-1,3,5-triazines is accompanied by intramolecular condensation and affords 2-aryl-4-arylamino-6-benzo[b]furan-2-yl-1,3,5-triazines.

  水杨醛和邻羟基苯乙酮与 2-氨基-4-芳基氨基-6-氯甲基-1,3,5-三嗪发生烷基化反应，同时发生分子内缩合反应，生成 2-芳基-4-芳基氨基-6-苯并[b]呋喃-2-基-1,3,5-三嗪。