4-chloro-6-nitro-2-(tosylmethyl)quinazoline | 1189329-81-4

• 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-chloro-6-nitro-2-(tosylmethyl)quinazoline
• 英文别名: 4-Chloro-2-[(4-methylphenyl)sulfonylmethyl]-6-nitroquinazoline
• CAS: 1189329-81-4
• 化学式: C₁₆H₁₂ClN₃O₄S
• 分子量: 377.808
• InChiKey: MHICWCJAFUEAIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chloro-6-nitro-2-(tosylmethyl)quinazoline 、 间氨基三氟甲苯 以 二氯甲烷 、 异丙醇 为溶剂， 反应 0.5h， 以75%的产率得到6-nitro-2-(tosylmethyl)-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine
  参考文献：
  名称：

  Original quinazoline derivatives displaying antiplasmodial properties

  摘要：

  The multistep synthesis of new quinazoline-derived molecules and their in vitro antiplasmodial evaluation on the W2 chloroquino-resistant Plasmodium falciparum strain is described herein. These molecules have also been studied concerning their in vitro cytotoxicity toward two human cell lines (K652 and HepG2) in order to calculate their respective selectivity indexes (S.I.). Among the fourteen tested molecules, two exhibited both significant antiplasmodial activity (IC50 = 0.95 and 1.3 mu M) and low toxicity (IC50 > 100 or 125 mu M), compared with two reference drugs: chloroquine and doxycycline. The structure activity relationships establish that the molecular scaffold which exerts the best profile is the 6-nitro-2-(tosylmethyl)-N-(3-substituted-phenyl)-quinazolin-4-amine. The hit molecules were finally investigated regarding their potential action toward two other protozoa, Leishmania donovani and Toxoplasma gondii, showing that these molecules display a selective antiplasmodial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.005
• 作为产物：
  描述：

  6-nitro-2-(tosylmethyl)quinazolin-4(3H)-one 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以74%的产率得到4-chloro-6-nitro-2-(tosylmethyl)quinazoline
  参考文献：
  名称：

  通过微波辐射 Suzuki-Miyaura 交叉偶联反应合成原始 2-取代 4-芳基喹唑啉

  摘要：

  使用微波辅助 Suzuki-Miyaura 交叉偶联方法合成了原始的 2-取代 4-芳基喹唑啉。本文描述了 2-取代 4-氯喹唑啉与各种硼酸之间 Suzuki-Miyaura 交叉偶联反应的优化和推广。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900421

文献信息

• Synthesis of Original 2-Substituted 4-Arylquinazolines by Microwave-Irradiated Suzuki-Miyaura Cross-Coupling Reactions
  作者：Youssef Kabri、Armand Gellis、Patrice Vanelle

  DOI：10.1002/ejoc.200900421

  日期：2009.8

  Original 2-substituted 4-arylquinazolines have been synthesized by using a microwave-assisted Suzuki–Miyaura cross-coupling approach. The optimization and generalization of the Suzuki–Miyaura cross-coupling reaction between 2-substituted 4-chloroquinazolines and various boronic acids are described herein. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  使用微波辅助 Suzuki-Miyaura 交叉偶联方法合成了原始的 2-取代 4-芳基喹唑啉。本文描述了 2-取代 4-氯喹唑啉与各种硼酸之间 Suzuki-Miyaura 交叉偶联反应的优化和推广。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Original quinazoline derivatives displaying antiplasmodial properties
  作者：Youssef Kabri、Nadine Azas、Aurélien Dumètre、Sébastien Hutter、Michèle Laget、Pierre Verhaeghe、Armand Gellis、Patrice Vanelle

  DOI：10.1016/j.ejmech.2009.11.005

  日期：2010.2

  The multistep synthesis of new quinazoline-derived molecules and their in vitro antiplasmodial evaluation on the W2 chloroquino-resistant Plasmodium falciparum strain is described herein. These molecules have also been studied concerning their in vitro cytotoxicity toward two human cell lines (K652 and HepG2) in order to calculate their respective selectivity indexes (S.I.). Among the fourteen tested molecules, two exhibited both significant antiplasmodial activity (IC50 = 0.95 and 1.3 mu M) and low toxicity (IC50 > 100 or 125 mu M), compared with two reference drugs: chloroquine and doxycycline. The structure activity relationships establish that the molecular scaffold which exerts the best profile is the 6-nitro-2-(tosylmethyl)-N-(3-substituted-phenyl)-quinazolin-4-amine. The hit molecules were finally investigated regarding their potential action toward two other protozoa, Leishmania donovani and Toxoplasma gondii, showing that these molecules display a selective antiplasmodial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.