2-(4-Methyl-1-piperazinyl)-4(3H)-quinazolinone | 16822-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(4-Methyl-1-piperazinyl)-4(3H)-quinazolinone
• 英文别名: 2-(4-methylpiperazin-1-yl)quinazolin-4(3H)-one；2-(N-Methyl-piperazino)-3H-chinazolon-4；2-(4-methyl-piperazin-1-yl)-3H-quinazolin-4-one；2-(4-methylpiperazin-1-yl)-3H-quinazolin-4-one
• CAS: 16822-65-4
• 化学式: C₁₃H₁₆N₄O
• 分子量: 244.296
• InChiKey: WWOMJAJTOOLHDS-UHFFFAOYSA-N

物化性质

• 熔点：
  225-228 °C
• 沸点：
  395.4±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Methyl-1-piperazinyl)-4(3H)-quinazolinone 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-氯-3-甲基苯氧基)-2-(4-甲基哌嗪-1-基)喹唑啉
  参考文献：
  名称：

  Novel 4-phenoxy-2-(1-piperazinyl)quinazolines as potent anticonvulsive and antihypoxic agents.

  摘要：

  一系列4-苯氧基-2-(1-哌嗪基)喹唑啉被合成并测试了其抗惊厥和抗缺氧活性。许多化合物的抗惊厥活性与卡马西平或苯妥英相当。其中，4-苯氧基-2-(4-丙基-1-哌嗪基)喹唑啉（5w）因其较少的副作用而成为最有前景的抗癫痫药物候选。似乎强大的抗惊厥活性是获得强大抗缺氧活性的先决条件。

  DOI：

  10.1248/cpb.38.681
• 作为产物：
  描述：

  2-巯基-4(3H)-喹唑酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 生成 2-(4-Methyl-1-piperazinyl)-4(3H)-quinazolinone
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationships of Highly Potent 5-HT₃ Receptor Ligands

  摘要：

  The 5-HT3 receptor, a pentameric ligand-gated ion channel (pLGIC), is an important therapeutic target. During a recent fragment screen, 6-chloro-N-methyl-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine (1) was identified as a 5-HT3R hit fragment. Here we describe the synthesis and structure activity relationships (SAR) of a series of (iso)quinoline and quinazoline compounds that were synthesized and screened for 5-HT3R affinity using a [H-3]granisetron displacement assay. These studies resulted in the discovery of several high affinity ligands of which compound 22 showed the highest affinity (pK(i) > 10) for the 5-HT3 receptor. The observed SAR is in agreement with established pharmacophore models for 5-HT3 ligands and is used for ligand-receptor binding mode prediction using homology modeling and in silico docking approaches.

  DOI：

  10.1021/jm300801u

文献信息

• Novel 4-substituted 2-piperazinylquinazolines as potent anticonvulsive and antihypoxic agents.
  作者：Manabu HORI、Ryuichi IEMURA、Hideaki HARA、Akio OZAKI、Takayuki SUKAMOTO、Hiroshi OHTAKA

  DOI：10.1248/cpb.38.1286

  日期：——

  Several types of quinazoline derivatives were prepared and examined for anticonvulsive and antihypoxic activities. Many compounds showed potent anticonvulsive activity, and their anticonvulsive profile is similar to that of phenytoin. The analysis of quantitative structure-activity relationships indicated that the anticonvulsive activity was parabolically related to the lipophilicity of the compounds

  制备了几种类型的喹唑啉衍生物，并检查了其抗惊厥和抗缺氧活性。许多化合物表现出有效的抗惊厥活性，其抗惊厥特征与苯妥英相似。定量结构-活性关系的分析表明，抗惊厥活性与化合物的亲脂性呈抛物线相关。大多数的4-烷氧基喹唑啉显示出有效的抗惊厥和抗缺氧活性。可以肯定的是，这些活动的效力之间存在良好的相关性。
• Synthesis of 2-aminoquinazolinc-4(3<i>H</i>)-one derivatives as potential potassium channel openers
  作者：BÉNÉDicte Erb、Rufine Akue、Benoît Rigo、Bernard Pirotte、Daniel Couturier

  DOI：10.1002/jhet.5570370206

  日期：2000.3

  Starting from 2-thioxoquinazolin-4-one, the synthesis of 2-amino-4(3H)-one derivatives, structurally related to potassium channels openers pinacidil and diazoxide, is described.

  从2-硫代喹唑啉-4-酮开始，描述了2-氨基-4（3 H）-一衍生物的合成，该衍生物在结构上与钾通道开放剂松那地尔和二氮嗪有关。
• Efficient Copper-Catalyzed Synthesis of 2-Amino-4(<i>3H</i>)-quinazolinone and 2-Aminoquinazoline Derivatives
  作者：Hua Fu、Renzhong Qiao、Xuhu Huang、Haijun Yang、Yufen Zhao

  DOI：10.1055/s-0029-1216871

  日期：——

  We have developed a versatile and efficient method for copper-catalyzed synthesis of both 2-amino-4(3H)-quinazolinone and 2-aminoquinazoline derivatives. The protocol uses readily available substituted 2-halobenzoic acids, 2-bromobenzaldehyde, 2-bromophenyl ketones and guanidines as the starting materials, inexpensive copper(I) iodide as the catalyst, and the method has important application values

  我们已经开发了一种通用且有效的方法，用于铜催化的2-氨基-4（3H）-喹唑啉酮和2-氨基喹唑啉衍生物的合成。该方案使用容易获得的取代的2-卤代苯甲酸，2-溴苯甲醛，2-溴苯基酮和胍作为起始原料，廉价的碘化亚铜（I）作为催化剂，该方法对于在N-杂环结构中的应用具有重要的应用价值。有机化学和药物化学。 铜催化-交叉偶联-2-氨基-4（3H）-喹唑啉酮-2-氨基喹唑啉-合成方法
• HORI, MANABU;IFMURA, RYUICHI;HARA, HIDEAKI;OZAKI, AKIO;SUKAMOTO, TAKAYUKI+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 681-687
  作者：HORI, MANABU、IFMURA, RYUICHI、HARA, HIDEAKI、OZAKI, AKIO、SUKAMOTO, TAKAYUKI+

  DOI：——

  日期：——
• HORI, MANABU;IEMURA, RYUICHI;HARA, HIDEAKI;OZAKI, AKIO;SUKAMOTO, TAKAYUKI+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1286-1291
  作者：HORI, MANABU、IEMURA, RYUICHI、HARA, HIDEAKI、OZAKI, AKIO、SUKAMOTO, TAKAYUKI+

  DOI：——

  日期：——