2-cyclohexyl-3-methylquinazolin-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: 2-cyclohexyl-3-methylquinazolin-4(3H)-one
• 英文别名: 2-Cyclohexyl-3-methylquinazolin-4-one
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: XMRHPAJSUZADQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.47
• 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：

  2-(cyclohexanecarboxamido)benzoic acid 在 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 51.0h， 生成 2-cyclohexyl-3-methylquinazolin-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

• Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes
  作者：Xiangyu Zhang、Chujun Luo、Xiaoyong Chen、Weilin Ma、Bin Li、Zirui Lin、Xiuwen Chen、Yibiao Li、Feng Xie

  DOI：10.1016/j.tetlet.2021.152835

  日期：2021.3

  A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate

  报道了一种新的催化体系，该结构通过碳负载的isatoic酸酐与酰胺和醛的酸催化级联反应来构建喹唑啉酮。随后还探索了使用氢转移策略对喹唑啉酮进行选择性加氢硅烷化以提供具有结构多样性的二氢喹唑啉。所开发的方法具有广泛的底物范围，出色的官能团耐受性，并利用了可重复使用的催化剂和空气作为绿色氧化剂。
• Nickel‐Catalyzed Intermolecular Branched/Linear Regioselective C−H Alkylation of 4‐Oxoquinazolines
  作者：Yaqi Zhang、Shengxiang Qin、Bendu Pan、Rihui Cao、Raymond Wai‐Yin Sun、Liqin Qiu

  DOI：10.1002/adsc.202201353

  日期：2023.2.21

  activated 4-oxoquinazolines with aryl and alkyl alkenes was demonstrated. When aryl alkenes are used as the substrates, the regioselection of the reaction can be fine-tuned by choosing a NHC ligand with appropriate steric hindrance to harvest branched adducts, while the use of a bulky NHC/alkyl aluminum cocatalyst system helps to steer the reaction towards linear products. For alkyl alkene substrates, Ni(cod)2

  展示了基于 C-H 活化的 4-氧代喹唑啉与芳基和烷基烯烃的烷基化反应的 Ni-NHC 催化的原型反应。当芳基烯烃用作底物时，可以通过选择具有适当空间位阻的 NHC 配体来微调反应的区域选择以收获支链加合物，而使用大体积 NHC/烷基铝助催化剂系统有助于控制反应对线性产品。对于烷基烯烃底物，Ni(cod) 2、IMes ⋅ HCl和NaO t Bu体系可以定向生成线性产物，长链烯烃也适用。此外，还通过氘化实验探索了催化机理，并提出了催化循环中镍的迁移。
• Efficient synthesis of pyrrolo[1,2-α]quinoxalines mediated by ethyl 2-(4-nitrophenyl)azocarboxylate
  作者：Da Hye Lee、Ga Young Kim、Jinho Kim

  DOI：10.1039/d2nj05259h

  日期：——

  The synthesis of pyrrolo[1,2-α]quinoxalines is of importance, because they possess a variety of biological activities, and interesting fluorescence/photophysical properties. Multifarious methods for the construction of pyrrolo[1,2-α]quinoxalines have been developed, but there remains no general means to exhibit broad substrate scope with high functional group tolerance under mild conditions. We report

  吡咯并 [1,2-α] 喹喔啉的合成非常重要，因为它们具有多种生物活性和有趣的荧光/光物理特性。已经开发了多种构建吡咯并[1,2-α]喹喔啉的方法，但仍然没有通用的方法在温和条件下表现出广泛的底物范围和高官能团耐受性。我们在此报告了使用 2-(4-硝基苯基) 偶氮甲酸乙酯对吡咯并 [1,2-α] 喹喔啉进行实用且有效的氧化环化。
• 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.