4-<<2-<(5,6-dichloro-1H-benzimidazol-2-yl)amino>-6-phenyl-4-pyrimidinyl>amino>-2-<(diethylamino)methyl>phenol | 86260-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-<<2-<(5,6-dichloro-1H-benzimidazol-2-yl)amino>-6-phenyl-4-pyrimidinyl>amino>-2-<(diethylamino)methyl>phenol
• 英文别名: 4-({2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-6-phenyl-4-pyrimidinyl}amino)-2-[(diethylamino)methyl]phenol；4-[[2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-6-phenylpyrimidin-4-yl]amino]-2-(diethylaminomethyl)phenol
• CAS: 86260-67-5
• 化学式: C₂₈H₂₇Cl₂N₇O
• 分子量: 548.475
• InChiKey: IUSPRQNLIOQSGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,5-二氯邻苯二胺 在 盐酸 、 potassium iodide 、 三氯氧磷 、 苯酚 作用下， 以 乙二醇乙醚 为溶剂， 反应 30.08h， 生成 4-<<2-<(5,6-dichloro-1H-benzimidazol-2-yl)amino>-6-phenyl-4-pyrimidinyl>amino>-2-<(diethylamino)methyl>phenol
  参考文献：
  名称：

  N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents

  摘要：

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.

  DOI：

  10.1021/jm00363a017

文献信息

• N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents
  作者：Mario M. Angelo、Daniel Ortwine、Donald F. Worth、Leslie M. Werbel

  DOI：10.1021/jm00363a017

  日期：1983.9

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.