4-(2'-chlorophenyl)amino-6-nitroquinazoline | 1428063-46-0

• 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: 4-(2'-chlorophenyl)amino-6-nitroquinazoline
• 英文别名: 4-(2-chlorophenylamino)-6-nitroquinazoline；N-(2-chlorophenyl)-6-nitroquinazolin-4-amine
• CAS: 1428063-46-0
• 化学式: C₁₄H₉ClN₄O₂
• 分子量: 300.704
• InChiKey: DBLULGWEQBKHBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2'-chlorophenyl)amino-6-nitroquinazoline 在 ammonium hydroxide 、 sodium dithionite 作用下， 以 水 为溶剂， 反应 0.5h， 以75%的产率得到N4-(2-Chlorophenyl)quinazoline-4,6-diamine
  参考文献：
  名称：

  Design, synthesis and in vitro anti-proliferative activity of 4,6-quinazolinediamines as potent EGFR-TK inhibitors

  摘要：

  4-Anilino-6-substituted-quinazolines were designed, synthesized and evaluated for EGFR-TK and tumor growth inhibitory activities. The target compounds were designed with enamine ester or urea moieties appended at the C-6 of quinazoline as additional hydrogen bond acceptor functions. Most of the synthesized compounds displayed potent EGFR-TK inhibitory activity at 10 mu M and the 6-ureido-anilinoquinazoline derivative 7a showed IC50 value of 0.061 mu M. Moreover, six compounds were tested by National Cancer Institute (NCI), USA for their anti-proliferative activity at 10 mu M in full NCI 60 cell panel. Compound 7a was further assayed for five dose molar ranges in full NCI 60 cell panel and exhibited remarkable growth inhibitory activity pattern against Non-Small Cell Lung Cancer EKVX (GI(50) = 037 mu M), NCI-H322M (GI(50) = 0.36 mu M), Renal Cancer A498 (GI(50) = 0.46 mu M), TK-10 (GI(50) = 0.99 mu M) and Breast Cancer MDA-MB-468 (GI(50) = 1.096 mu M) which are of high EGFR expression. Docking study was performed for the active compounds into ATP binding site of EGFR-TK which showed similar binding mode to gefitinib and additional binding with Cys-773 at the gatekeeper of EGFR-TK enzyme. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.017
• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 溶剂黄146 作用下， 反应 1.5h， 生成 4-(2'-chlorophenyl)amino-6-nitroquinazoline
  参考文献：
  名称：

  4-Arylamino-6-nitroquinazolines: Synthesis and their activities against neglected disease leishmaniasis

  摘要：

  4-Arylamino-6-nitroquinazolines (2-25) were synthesized and evaluated for their leishmanicidal activities against Leishmania major promastigotes in vitro with IC50 values = 1.87-61.48 mu M. Among the twenty four synthetic derivatives, 4-[4'-(methylsulfanyl)phenyljamino-6-nitroquinazoline (21), and 4-(2'-methoxyphenyl)amino-6-nitroquinazoline (8) showed excellent antileishmanial activities with IC50 values 1.87 +/- 0.31 and 437 +/- 0.02 mu M, respectively, more active than the standard drug, pentamidine (IC50 = 5.09 +/- 0.09 mu M). Compound 16 (IC50 = 6.53 +/- 0.21 mu M) displayed an activity comparable to the standard. Compounds 15 (IC50 = 9.04 +/- 0.03 mu M), 18 (IC50 = 12.28 +/- 0.18 mu M),14 (IC50 = 19.87 +/- 0.22 mu M), and 5 (IC50 = 24.03 +/- 2.71 mu M) also showed good activities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.016

文献信息

• Design, synthesis and in vitro anti-proliferative activity of 4,6-quinazolinediamines as potent EGFR-TK inhibitors
  作者：Samar Mowafy、Nahla A. Farag、Khaled A.M. Abouzid

  DOI：10.1016/j.ejmech.2012.10.017

  日期：2013.3

  4-Anilino-6-substituted-quinazolines were designed, synthesized and evaluated for EGFR-TK and tumor growth inhibitory activities. The target compounds were designed with enamine ester or urea moieties appended at the C-6 of quinazoline as additional hydrogen bond acceptor functions. Most of the synthesized compounds displayed potent EGFR-TK inhibitory activity at 10 mu M and the 6-ureido-anilinoquinazoline derivative 7a showed IC50 value of 0.061 mu M. Moreover, six compounds were tested by National Cancer Institute (NCI), USA for their anti-proliferative activity at 10 mu M in full NCI 60 cell panel. Compound 7a was further assayed for five dose molar ranges in full NCI 60 cell panel and exhibited remarkable growth inhibitory activity pattern against Non-Small Cell Lung Cancer EKVX (GI(50) = 037 mu M), NCI-H322M (GI(50) = 0.36 mu M), Renal Cancer A498 (GI(50) = 0.46 mu M), TK-10 (GI(50) = 0.99 mu M) and Breast Cancer MDA-MB-468 (GI(50) = 1.096 mu M) which are of high EGFR expression. Docking study was performed for the active compounds into ATP binding site of EGFR-TK which showed similar binding mode to gefitinib and additional binding with Cys-773 at the gatekeeper of EGFR-TK enzyme. (C) 2012 Elsevier Masson SAS. All rights reserved.
• 4-Arylamino-6-nitroquinazolines: Synthesis and their activities against neglected disease leishmaniasis
  作者：Syed Muhammad Saad、Nida Ghouri、Shahnaz Perveen、Khalid Mohammed Khan、M. Iqbal Choudhary

  DOI：10.1016/j.ejmech.2015.11.016

  日期：2016.1

  4-Arylamino-6-nitroquinazolines (2-25) were synthesized and evaluated for their leishmanicidal activities against Leishmania major promastigotes in vitro with IC50 values = 1.87-61.48 mu M. Among the twenty four synthetic derivatives, 4-[4'-(methylsulfanyl)phenyljamino-6-nitroquinazoline (21), and 4-(2'-methoxyphenyl)amino-6-nitroquinazoline (8) showed excellent antileishmanial activities with IC50 values 1.87 +/- 0.31 and 437 +/- 0.02 mu M, respectively, more active than the standard drug, pentamidine (IC50 = 5.09 +/- 0.09 mu M). Compound 16 (IC50 = 6.53 +/- 0.21 mu M) displayed an activity comparable to the standard. Compounds 15 (IC50 = 9.04 +/- 0.03 mu M), 18 (IC50 = 12.28 +/- 0.18 mu M),14 (IC50 = 19.87 +/- 0.22 mu M), and 5 (IC50 = 24.03 +/- 2.71 mu M) also showed good activities. (C) 2015 Elsevier Masson SAS. All rights reserved.