6,7-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one | 708268-03-5

• 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: 6,7-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one
• 英文别名: 6,7-dimethoxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one；6,7-Dimethoxy-2,2-dimethyl-1,3-dihydroquinazolin-4-one
• CAS: 708268-03-5
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: YVMUGDPTALSRQP-UHFFFAOYSA-N

物化性质

• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one 在 劳森试剂 作用下， 生成 6,7-dimethoxy-2,2-dimethyl-4-methylsulfanyl-1,2-dihydro-quinazoline
  参考文献：
  名称：

  Synthesis and biological evaluation of benzamides and benzamidines: structural requirement of a pyrimidine ring for inhibition of EGFR tyrosine kinase

  摘要：

  The benzamides 1 and the benzamidines 2-3 were synthesized as the mimics of 4-anilinoquinazolines, which possess inhibition of epidermal growth factor receptor (EGER) tyrosine kinase, and tested for cytotoxicity toward A431 and inhibitory activity toward autophosphorylation by the enzyme assay. High cell growth inhibition was observed in a series of the cyclic benzamides 3: the IC50 values are 0.09-0.32 mM. The benzamidines 3a and 3b exhibited high inhibition of EGER tyrosine kinase at a 1.0 muM concentration, although the benzamides 1 and the benzamidines 2 did not show significant kinase inhibition at a 10 muM concentration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.001
• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氨 、 1-羟基苯并三唑 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 6,7-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of benzamides and benzamidines: structural requirement of a pyrimidine ring for inhibition of EGFR tyrosine kinase

  摘要：

  The benzamides 1 and the benzamidines 2-3 were synthesized as the mimics of 4-anilinoquinazolines, which possess inhibition of epidermal growth factor receptor (EGER) tyrosine kinase, and tested for cytotoxicity toward A431 and inhibitory activity toward autophosphorylation by the enzyme assay. High cell growth inhibition was observed in a series of the cyclic benzamides 3: the IC50 values are 0.09-0.32 mM. The benzamidines 3a and 3b exhibited high inhibition of EGER tyrosine kinase at a 1.0 muM concentration, although the benzamides 1 and the benzamidines 2 did not show significant kinase inhibition at a 10 muM concentration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.001

文献信息

• The Divergent Transformations of Aromatic<i>o</i>-Aminonitrile with Carbonyl Compound
  作者：Jianhong Tang、Jiarong Li、Lijun Zhang、Shuling Ma、Daxin Shi、Qi Zhang、Liupan Yang、Xiuzhen Wang、Xuan Liu、Change Liu

  DOI：10.1002/jhet.804

  日期：2012.5

  A modified Friedländer conversion of the cyclocondensation of aromatic o‐aminonitriles with carbonyl compounds was discovered. Systematic studies reveal that both the new transformation and the classic Friedländer annulation in the presence of ZnCl2 constitute a pair of divergent reaction, and thecontrolled PDF transformation of this divergent reaction was achieved in the present of bases.

  发现了芳族邻氨基腈与羰基化合物的环缩合反应的改进的Friedländer转化。系统研究表明，在存在ZnCl 2的情况下，新的转化和经典的Friedländer圆环构成了一对发散反应，并且在碱的存在下实现了该发散反应的受控PDF转化。
• Benzamides and benzamidines as specific inhibitors of epidermal growth factor receptor and v-Src protein tyrosine kinases
  作者：Toru Asano、Tomohiro Yoshikawa、Taikou Usui、Hiroshi Yamamoto、Yoshinori Yamamoto、Yoshimasa Uehara、Hiroyuki Nakamura

  DOI：10.1016/j.bmc.2004.04.030

  日期：2004.7

  The benzamides 1 and the benzamidines 2 as well as the cyclic benzamidines 3 were designed and synthesized as the mimics of 4-anilinoquinazolines for an inhibitor of EGFR tyrosine kinase. The specific inhibitions of EGFR tyrosine kinase were observed in the benzamides 1c and 1d, and the benzamidine 2a, whereas the specific inhibitions of v-Src kinase were observed in the benzamide 1j and the benzamidine 2d at a 10 mug/mL concentration of compounds. The cyclic benzamidines 3a and 3b showed potent kinase inhibition of EGFR at a 1.0 mug/mL concentration. According to the docking simulation using the X-ray structure of EGFR kinase domain in complex with erlotimb, the LigScore2 scoring function value of erlotimb was calculated as 5.61, whereas that of the benzamide 1c was 5.05. In a similar manner, the LigScore2 value of the cyclic benzamidine 3a was calculated as 5.10. (C) 2004 Elsevier Ltd. All rights reserved.