6-chloro-2-cyclohexylquinazolin-4(3H)-one

• 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-chloro-2-cyclohexylquinazolin-4(3H)-one
• 英文别名: 6-Chloro-2-cyclohexyl-4(3H)-quinazolinone；6-chloro-2-cyclohexyl-3H-quinazolin-4-one
• 化学式: C₁₄H₁₅ClN₂O
• 分子量: 262.739
• InChiKey: GINVXGSOAIDYEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-Chloro-2-cyclohexyl-3,1-benzoxazin-4-one 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以87%的产率得到6-chloro-2-cyclohexylquinazolin-4(3H)-one
  参考文献：
  名称：

  4-Quinazolinones: synthesis and reduction of prostaglandin E2 production

  摘要：

  We synthesized and evaluated the anti-inflammatory activity of a series of 4-quinazolinone derivatives. Two approaches were used to yield the title compounds. A first group of quinazolinone derivatives was obtained by the appropriate substituted anthranilates. A second group of quinazolinone compounds was prepared through the benzoxazin-4-ones intermediate. The pharmacological results reveal that the synthesized derivatives exhibit a significant anti-inflammatory effect in an experimental ocular inflammation model. In fact, all the tested compounds lowered the prostaglandin E-2 (PGE(2)) production with respect to the control group (P < 0.05). The 3-cyclohexyl-6-chloro-quinazolin-4(3H)-one and 3-cyclohexyl-quinazolin-4(3H)-one derivatives were the most active compounds. These compounds significantly reduced PGE(2) levels even more than the reference drug tolmetin and significantly lower protein concentration and polymorphonuclear leukocytes number compared to the control group (P < 0.05). Therefore, these compounds may be useful to prevent ocular inflammatory reactions. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00102-0

文献信息

• Metal-Free C-2-H Alkylation of Quinazolin-4-ones with Alkanes via Cross-Dehydrogenative Coupling
  作者：Shuai Mao、Kaixiu Luo、Lu Wang、Hong-Yi Zhao、Andrea Shergalis、Minhang Xin、Nouri Neamati、Yi Jin、San-Qi Zhang

  DOI：10.1021/acs.orglett.9b00638

  日期：2019.4.5

  A practically useful approach for the cross-dehydrogenative coupling of quinazolin-4-one with simple nonactivated alkanes is reported. The products were smoothly formed under mild reaction conditions, within short reaction time at ambient temperature. The formation of new Csp3-Csp2 bonds occurred at the electron-poor C-2 position of quinazolin-4-one. The approach has the potential to be an important

  报道了一种用于喹唑啉-4-酮与简单的未活化烷烃的交叉脱氢偶联的实用方法。在温和的反应条件下，在环境温度下短的反应时间内，可以平稳地形成产物。新的Csp 3 -Csp 2键的形成发生在喹唑啉-4-one的电子贫乏的C-2位。该方法有可能成为高级合成中间体后期功能化的重要工具，并可能在药物化学中找到许多应用。
• 4-Quinazolinones: synthesis and reduction of prostaglandin E2 production
  作者：Natale Alfredo Santagati、Ennio Bousquet、Angelo Spadaro、Giuseppe Ronsisvalle

  DOI：10.1016/s0014-827x(99)00102-0

  日期：1999.11

  We synthesized and evaluated the anti-inflammatory activity of a series of 4-quinazolinone derivatives. Two approaches were used to yield the title compounds. A first group of quinazolinone derivatives was obtained by the appropriate substituted anthranilates. A second group of quinazolinone compounds was prepared through the benzoxazin-4-ones intermediate. The pharmacological results reveal that the synthesized derivatives exhibit a significant anti-inflammatory effect in an experimental ocular inflammation model. In fact, all the tested compounds lowered the prostaglandin E-2 (PGE(2)) production with respect to the control group (P < 0.05). The 3-cyclohexyl-6-chloro-quinazolin-4(3H)-one and 3-cyclohexyl-quinazolin-4(3H)-one derivatives were the most active compounds. These compounds significantly reduced PGE(2) levels even more than the reference drug tolmetin and significantly lower protein concentration and polymorphonuclear leukocytes number compared to the control group (P < 0.05). Therefore, these compounds may be useful to prevent ocular inflammatory reactions. (C) 1999 Elsevier Science S.A. All rights reserved.