6-chloro-3-cyclohexylquinazolin-4(3H)-one | 92194-60-0

• 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: 6-chloro-3-cyclohexylquinazolin-4(3H)-one
• 英文别名: 6-Chloro-3-cyclohexylquinazolin-4-one
• CAS: 92194-60-0
• 化学式: C₁₄H₁₅ClN₂O
• 分子量: 262.739
• InChiKey: RIQHCBWGJKMJIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-2-甲酰氨基苯甲酸 、 环己胺 在 吡啶 、 三氯化磷 作用下， 反应 1.5h， 以41%的产率得到6-chloro-3-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

• Base-promoted ring opening of 3-chlorooxindoles for the construction of 2-aminoarylthioates and their transformation to quinazolin-4(3<i>H</i>)-ones
  作者：Tej Narayan Poudel、Hari Datta Khanal、Yong Rok Lee

  DOI：10.1039/c8nj00195b

  日期：——

  Cesium carbonate-promoted synthesis of diverse 2-aminoarylthioatesviaring opening of 3-chlorooxindoles with thiols, and their synthetic applications is demonstrated.

  铯碳酸盐促进的多样化2-氨基芳基硫酸酯的合成通过3-氯氧吲哚与硫醇的环开启反应，并展示了它们的合成应用。
• Discovery of molluscicidal and cercaricidal activities of 3-substituted quinazolinone derivatives by a scaffold hopping approach using a pseudo-ring based on the intramolecular hydrogen bond formation
  作者：Wei Guo、Lv-Yin Zheng、Yong-Dong Li、Ren-Miao Wu、Qiang Chen、Ding-Qiao Yang、Xiao-Lin Fan

  DOI：10.1016/j.ejmech.2016.03.037

  日期：2016.6

  in current Schistosomiasis control. A pseudo-ring formed from salicylanilide by an intramolecular hydrogen bond led to the discovery of 3-substituted quinazolinone derivatives which showed a potent molluscicidal and cercaricidal activities.

  在目前的血吸虫病控制中，发现针对钉螺和尾c的新型拓扑剂仍然是一项重大挑战。由水杨酰苯胺通过分子内氢键形成的假环导致发现了具有强力杀灭杀虫和杀菌作用的3-取代的喹唑啉酮衍生物。
• Solvent-Free Reaction between Anthranilic Acids and Isocyanides: A Novel Approach for the Synthesis of 2-Unsubstituted 4(3H)-Quinazolinones
  作者：Mehdi Adib、Morteza Karimzadeh、Mohammad Mahdavi、Ehsan Sheikhi、Peiman Mirzaei

  DOI：10.1055/s-0030-1259909

  日期：2011.4

  A novel synthesis of 2-unsubstituted 4(3H)-quinazolino- nes is described. Heating a mixture of an anthranilic acid and an iso- cyanide under solvent-free conditions afforded the title compounds in good to excellent yields.

  描述了 2-未取代的 4(3H)-喹唑啉酮的新合成。在无溶剂条件下加热邻氨基苯甲酸和异氰化物的混合物以良好至极好的产率提供标题化合物。