3,4-dihydroquinazolin-2-yl guanidine | 90887-39-1

• 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: 3,4-dihydroquinazolin-2-yl guanidine
• 英文别名: (3,4-dihydro-quinazolin-2-yl)-guanidine；2-(1,4-Dihydroquinazolin-2-yl)guanidine；2-(1,4-dihydroquinazolin-2-yl)guanidine
• CAS: 90887-39-1
• 化学式: C₉H₁₁N₅
• 分子量: 189.22
• InChiKey: PBCMDFZWJIXDKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  88.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 3,4-dihydroquinazolin-2-yl guanidine 在 吡啶 作用下， 反应 5.0h， 以52%的产率得到2-amino-6H-[1,3,5]triazino[2,1-b]quinazolin-4-thione (12).
  参考文献：
  名称：

  Synthesis and Heterocyclizations of 3,4-Dihydroquinazolin-2-yl Guanidine in the Search of New Anticancer Agents

  摘要：

  The cyclocondensations of 3,4-dihydroquinazolin-2-yl guanidine with a variety of electrophilic reagents viz. aldehydes, ketones, triethyl orthoformate, diethyl ethoxymethylenemalonate, carbon disulfide and trichloroacetonitrile were found to afford 1,3,5-triazino[2,1-b]quinazolines. However, some unexpected reactions were also observed. The structural properties such as tautomerism and hinderance to conformational rotation were also investigated. The results of biological testing suggested that the 1,3,5-triazino[2,1-b]quinazoline nucleus could be a new promising scaffold for the development of potential anticancer agents.

  DOI：

  10.3987/com-09-11672
• 作为产物：
  描述：

  二聚氰胺 、 2-氨基苄胺 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 18.17h， 以74%的产率得到3,4-dihydroquinazolin-2-yl guanidine
  参考文献：
  名称：

  Synthesis and Heterocyclizations of 3,4-Dihydroquinazolin-2-yl Guanidine in the Search of New Anticancer Agents

  摘要：

  The cyclocondensations of 3,4-dihydroquinazolin-2-yl guanidine with a variety of electrophilic reagents viz. aldehydes, ketones, triethyl orthoformate, diethyl ethoxymethylenemalonate, carbon disulfide and trichloroacetonitrile were found to afford 1,3,5-triazino[2,1-b]quinazolines. However, some unexpected reactions were also observed. The structural properties such as tautomerism and hinderance to conformational rotation were also investigated. The results of biological testing suggested that the 1,3,5-triazino[2,1-b]quinazoline nucleus could be a new promising scaffold for the development of potential anticancer agents.

  DOI：

  10.3987/com-09-11672

文献信息

• Synthesis and Heterocyclizations of 3,4-Dihydroquinazolin-2-yl Guanidine in the Search of New Anticancer Agents
  作者：Wai Keung Chui、Anton V. Dolzhenko、Anna V. Dolzhenko、Mi Chelle Foo、Bee Jen Tan、Gigi Ngar Chee Chiu

  DOI：10.3987/com-09-11672

  日期：——

  The cyclocondensations of 3,4-dihydroquinazolin-2-yl guanidine with a variety of electrophilic reagents viz. aldehydes, ketones, triethyl orthoformate, diethyl ethoxymethylenemalonate, carbon disulfide and trichloroacetonitrile were found to afford 1,3,5-triazino[2,1-b]quinazolines. However, some unexpected reactions were also observed. The structural properties such as tautomerism and hinderance to conformational rotation were also investigated. The results of biological testing suggested that the 1,3,5-triazino[2,1-b]quinazoline nucleus could be a new promising scaffold for the development of potential anticancer agents.