3-amino-2-benzylaminoquinazolin-4(3H)-one | 623573-77-3

• 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: 3-amino-2-benzylaminoquinazolin-4(3H)-one
• 英文别名: 3-amino-2-benzylamino-3H-quinazolin-4-one；3-Amino-2-[(phenylmethyl)amino]-4(3H)-quinazolinone；3-amino-2-(benzylamino)quinazolin-4-one
• CAS: 623573-77-3
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: MDHHFEDFCLNYEN-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C(Solv: ethanol (64-17-5))
• 沸点：
  475.3±38.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-2-benzylaminoquinazolin-4(3H)-one 在 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 38.0h， 生成 3-Benzyl-2-(morpholin-4-ylmethyl)-[1,2,4]triazolo[5,1-b]quinazolin-9-one
  参考文献：
  名称：

  Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones

  摘要：

  A series of 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones have been synthesized by the cyclocondensation of 3-amino-2-benzylamino-3H-quinazolin-4-one with a variety of one-carbon donors. The starting material 3-amino-2-benzyl-amino- 3H-quinazolin-4-one was synthesized from methyl anthranilate by a novel innovative route. The title compounds were evaluated for their in vivo antihypertensive activity using spontaneously hypertensive rats (SHR). While all the test compounds exhibited significant antihypertensive activity, 3-benzyl-2-methyl-3H-[1,2,4]triazolo[5,1-b] quinazolin-9-one exhibited antihypertensive activity more than the reference standard prazocin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.007
• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 49.5h， 生成 3-amino-2-benzylaminoquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones

  摘要：

  A series of 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones have been synthesized by the cyclocondensation of 3-amino-2-benzylamino-3H-quinazolin-4-one with a variety of one-carbon donors. The starting material 3-amino-2-benzyl-amino- 3H-quinazolin-4-one was synthesized from methyl anthranilate by a novel innovative route. The title compounds were evaluated for their in vivo antihypertensive activity using spontaneously hypertensive rats (SHR). While all the test compounds exhibited significant antihypertensive activity, 3-benzyl-2-methyl-3H-[1,2,4]triazolo[5,1-b] quinazolin-9-one exhibited antihypertensive activity more than the reference standard prazocin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.007

文献信息

• Synthesis, Analgesic and Anti-inflammatory Activities of Some Novel 2,3-Disubstituted Quinazolin-4(3H)-ones.
  作者：Veerachamy Alagarsamy、Veluchamy Muthukumar、Nagendran Pavalarani、Poongavanam Vasanthanathan、Rajappan Revathi

  DOI：10.1248/bpb.26.557

  日期：——

  A series of novel 2-benzylamino-3-substituted quinazolin-4(3H)-ones have been synthesized by treating 3-amino-2-benzylamino quinazolin-4(3H)-one, with different aldehydes and ketones. The starting material 3-amino-2-benzylamino quinazolin-4(3H)-one was synthesized by nucleophilic substitution of thiomethyl group of 3-amino-2-methylthio quinazolin-4(3H)-one by benzylamine. The title compounds were investigated for analgesic and anti-inflammatory activities. All the test compounds exhibited significant analgesic activity, whereas the compound III is equipotent with diclofenac sodium. The compounds I, II and III showed more potent anti-inflammatory activity than diclofenac sodium.

  通过用不同的醛和酮处理3-氨基-2-苄氨基喹唑啉-4(3H)-酮，合成了一系列新型2-苄氨基-3-取代的喹唑啉-4(3H)-酮。以3-氨基-2-甲硫基喹唑啉-4(3H)-酮的硫甲基被苄胺亲核取代，合成了起始原料3-氨基-2-苄氨基喹唑啉-4(3H)-酮。研究了标题化合物的镇痛和抗炎活性。所有测试化合物均表现出显着的镇痛活性，而化合物III与双氯芬酸钠等效。化合物I、II和III显示出比双氯芬酸钠更有效的抗炎活性。