([1,3]dioxolo[4,5-g]quinazolin-8-yl)-(4'-bromo-2'-fluorophenyl)amine hydrochloride | 1266869-09-3

• 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: ([1,3]dioxolo[4,5-g]quinazolin-8-yl)-(4'-bromo-2'-fluorophenyl)amine hydrochloride
• 英文别名: 4-(4-bromo-2-fluoroanilino)-6,7-methylenedioxyquinazoline hydrochloride；N-(4-bromo-2-fluorophenyl)-[1,3]dioxolo[4,5-g]quinazolin-8-amine;hydrochloride
• CAS: 1266869-09-3
• 化学式: C₁₅H₉BrFN₃O₂*ClH
• 分子量: 398.619
• InChiKey: DYOBLHCLDLLBKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ([1,3]dioxolo[4,5-g]quinazolin-8-yl)-(4'-bromo-2'-fluorophenyl)amine hydrochloride 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.0h， 以38%的产率得到4-(N-methyl-4-bromo-2-fluoroanilino)-6,7-methylenedioxyquinazoline
  参考文献：
  名称：

  Design, Synthesis, and DNA-Binding of N-Alkyl(anilino)quinazoline Derivatives

  摘要：

  New N-alkylanilinoquinazoline derivatives 5, 12, 20, and 22 have been prepared Crow 4-chloro-6, 7-dimethoxyquinazoline 3, 4-chloro-6,7-methylenedioxyquinazoline 19, and commercially available anilines. Differents classes of compounds substituted by an aryloxygroup (6a-c. 16a,b, and 17a,b). (aminophenyl)ureas (12a,b and 13a-f), anilines (4a-m, 20a,b), N-alkyl(aniline) (5a-m, 21a,b. 22a,d). and N-aminoalkyl(aniline) (22e-g) have been synthesized. These molecules were evaluated for then. cytotoxic activities and as potential DNA intercalating agents. We studied the strength and mode of binding to DNA of these molecules by DNA melting temperature measurements, fluorescence emission. and circular dichroism. The results of various spectral and gel electrophoresis techniques obtained with the different compounds, in particular compounds 5g and 22f, revealed significant DNA interaction. These experiments confirm that the N-aminoalkyl(anilino)-6,7-dimethoxyquinazoline nucleus is an efficient pharmacophore to trigger binding to DNA, via an intercalative binding process.

  DOI：

  10.1021/jm1009605
• 作为产物：
  描述：

  胡椒酸 在 氯化亚砜 、 氢气 、 硝酸 、 sodium methylate 、 四氯化锡 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 3.0h， 生成 ([1,3]dioxolo[4,5-g]quinazolin-8-yl)-(4'-bromo-2'-fluorophenyl)amine hydrochloride
  参考文献：
  名称：

  Design, Synthesis, and DNA-Binding of N-Alkyl(anilino)quinazoline Derivatives

  摘要：

  New N-alkylanilinoquinazoline derivatives 5, 12, 20, and 22 have been prepared Crow 4-chloro-6, 7-dimethoxyquinazoline 3, 4-chloro-6,7-methylenedioxyquinazoline 19, and commercially available anilines. Differents classes of compounds substituted by an aryloxygroup (6a-c. 16a,b, and 17a,b). (aminophenyl)ureas (12a,b and 13a-f), anilines (4a-m, 20a,b), N-alkyl(aniline) (5a-m, 21a,b. 22a,d). and N-aminoalkyl(aniline) (22e-g) have been synthesized. These molecules were evaluated for then. cytotoxic activities and as potential DNA intercalating agents. We studied the strength and mode of binding to DNA of these molecules by DNA melting temperature measurements, fluorescence emission. and circular dichroism. The results of various spectral and gel electrophoresis techniques obtained with the different compounds, in particular compounds 5g and 22f, revealed significant DNA interaction. These experiments confirm that the N-aminoalkyl(anilino)-6,7-dimethoxyquinazoline nucleus is an efficient pharmacophore to trigger binding to DNA, via an intercalative binding process.

  DOI：

  10.1021/jm1009605

文献信息

• Exploring Epidermal Growth Factor Receptor (EGFR) Inhibitor Features: The Role of Fused Dioxygenated Rings on the Quinazoline Scaffold
  作者：Adriana Chilin、Maria Teresa Conconi、Giovanni Marzaro、Adriano Guiotto、Luca Urbani、Francesca Tonus、Pierpaolo Parnigotto

  DOI：10.1021/jm901338g

  日期：2010.2.25

  A number of dioxolane, dioxane, and dioxepine quinazoline derivatives have been synthetized and evaluated as EGFR inhibitors. Their cytotoxic activity has been tested against two cell lines overexpressing and not expressing EGFR. Most derivatives were able to counteract EGF-induced EGFR phosphorylation, and their potency was comparable to the reference compound PD153035. The size of the fused dioxygenated

  已经合成了许多二氧戊环，二氧六环和二氧杂环庚烷喹唑啉衍生物，并将其评估为EGFR抑制剂。已经针对两种过表达和不表达EGFR的细胞系测试了它们的细胞毒性活性。大多数衍生物能够抵消EGF诱导的EGFR磷酸化，其效价与参考化合物PD153035相当。稠合的双加氧环的大小对于生物活性至关重要，二恶烷衍生物是该系列中最有前途的一类。
• Design, Synthesis, and DNA-Binding of <i>N</i>-Alkyl(anilino)quinazoline Derivatives
  作者：Antonio Garofalo、Laurence Goossens、Brigitte Baldeyrou、Amélie Lemoine、Séverine Ravez、Perrine Six、Marie-Hélène David-Cordonnier、Jean-Paul Bonte、Patrick Depreux、Amélie Lansiaux、Jean-François Goossens

  DOI：10.1021/jm1009605

  日期：2010.11.25

  New N-alkylanilinoquinazoline derivatives 5, 12, 20, and 22 have been prepared Crow 4-chloro-6, 7-dimethoxyquinazoline 3, 4-chloro-6,7-methylenedioxyquinazoline 19, and commercially available anilines. Differents classes of compounds substituted by an aryloxygroup (6a-c. 16a,b, and 17a,b). (aminophenyl)ureas (12a,b and 13a-f), anilines (4a-m, 20a,b), N-alkyl(aniline) (5a-m, 21a,b. 22a,d). and N-aminoalkyl(aniline) (22e-g) have been synthesized. These molecules were evaluated for then. cytotoxic activities and as potential DNA intercalating agents. We studied the strength and mode of binding to DNA of these molecules by DNA melting temperature measurements, fluorescence emission. and circular dichroism. The results of various spectral and gel electrophoresis techniques obtained with the different compounds, in particular compounds 5g and 22f, revealed significant DNA interaction. These experiments confirm that the N-aminoalkyl(anilino)-6,7-dimethoxyquinazoline nucleus is an efficient pharmacophore to trigger binding to DNA, via an intercalative binding process.