N2-(5,6-Dichloro-1H-benzoimidazol-2-yl)-N4-(3-diethylaminomethyl-4-ethoxy-phenyl)-5,6,7,8-tetrahydro-quinazoline-2,4-diamine; hydrochloride | 86260-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N2-(5,6-Dichloro-1H-benzoimidazol-2-yl)-N4-(3-diethylaminomethyl-4-ethoxy-phenyl)-5,6,7,8-tetrahydro-quinazoline-2,4-diamine; hydrochloride
• CAS: 86260-65-3
• 化学式: C₂₈H₃₃Cl₂N₇O*2ClH
• 分子量: 627.444
• InChiKey: OVTFNYBAJYGWCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  90.99
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-<(5,6-dichloro-1H-benzimidazol-2-yl)amino>-5,6,7,8-tetrahydro-4-quinazolinol 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N2-(5,6-Dichloro-1H-benzoimidazol-2-yl)-N4-(3-diethylaminomethyl-4-ethoxy-phenyl)-5,6,7,8-tetrahydro-quinazoline-2,4-diamine; hydrochloride
  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