3-butyl-2-methylquinazolin-4(3H)-one | 394-90-1

• 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: 3-butyl-2-methylquinazolin-4(3H)-one
• 英文别名: 2-Methyl-3-butyl-3.4-dihydro-4-chinazolinon；2-Methyl-3-butyl-4-chinazolinon；2-Methyl-3-butyl-chinazolon-(4)；2-Methyl-3-n-butylchinazolon；3-butyl-2-methyl-3H-quinazolin-4-one；3-Butyl-2-methyl-3H-chinazolin-4-on；4-Quinazolone, 3-butyl-2-methyl；3-butyl-2-methylquinazolin-4-one
• CAS: 394-90-1
• 化学式: C₁₃H₁₆N₂O
• mdl: MFCD02958754
• 分子量: 216.283
• InChiKey: WBYGSYVGRKQFJY-UHFFFAOYSA-N

物化性质

• 保留指数：
  1915;1915

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-butyl-2-methylquinazolin-4(3H)-one 以80%的产率得到
  参考文献：
  名称：

  BADR M. Z. A.; EL-SHERIEF H. A. H.; ALY M. M., INDIAN J. CHEM. , 1975, 13, NO 3, 245-247

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-n-丁基苯甲酰胺 在 copper(I) oxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三环己基膦 作用下， 以 氯仿 为溶剂， 反应 25.0h， 生成 3-butyl-2-methylquinazolin-4(3H)-one
  参考文献：
  名称：

  铜催化 2-氨基苯甲酰胺与叔胺串联反应合成喹唑啉酮衍生物

  摘要：

  我们开发了铜催化的 2-氨基苯甲酰胺与叔胺的串联反应，用于形成喹唑啉酮衍生物。该策略包括在一锅中进行的两个步骤（环化和偶联）。许多底物在标准条件下反应良好，以中等至良好的产率得到相应的喹唑啉酮衍生物。

  DOI：

  10.1055/s-0036-1588881

文献信息

• A novel superparamagnetic powerful guanidine-functionalized γ-Fe₂O₃ based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4(3<i>H</i>)-one derivatives in Green media
  作者：Fateme Haji Norouzi、Naser Foroughifar、Alireza Khajeh-Amiri、Hoda Pasdar

  DOI：10.1039/d1ra05560g

  日期：——

  novel organic–inorganic nanohybrid superparamagnetic (γ-Fe2O3@CPTMS–guanidine@SO3H) nanocatalyst modified with sulfonic acid represents an efficient and green catalyst for the one-pot synthesis of quinazolin-4(3H)-one derivatives via three-component condensation reaction between anthranilic acid, acetic anhydride and different amines under microwave irradiation and solvent-free conditions (4a–q). XRD,

  用磺酸改性的新型有机-无机纳米杂化超顺磁性（γ-Fe 2 O 3 @CPTMS-guanidine@SO 3 H）纳米催化剂代表了一锅法合成quinazolin-4(3 H )-one的高效绿色催化剂在微波辐射和无溶剂条件下，邻氨基苯甲酸、乙酸酐和不同胺之间的三组分缩合反应生成衍生物（4a - q）。XRD、FT-IR、FE-SEM、TGA、VSM 和 EDX 用于表征这种新型磁性有机催化剂。性能突出、响应时间短（15-30分钟）、操作简单、后处理简单、避免有毒催化剂是其显着优势。此外，它可以很容易地通过使用外部磁体的磁倾析从反应溶液中分离出来，并且可以循环至少六次而不会显着降低其活性。
• Nielsen, Knud Erik; Pedersen, Erik B., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 9, p. 637 - 642
  作者：Nielsen, Knud Erik、Pedersen, Erik B.

  DOI：——

  日期：——
• Rapid synthesis of 2,3-disubstituted-quinazolin-4-ones enhanced by microwave-assisted decomposition of formamide
  作者：Ioannis K. Kostakis、Abdelhakim Elomri、Elisabeth Seguin、Mauro Iannelli、Thierry Besson

  DOI：10.1016/j.tetlet.2007.07.114

  日期：2007.9

  An efficient methodology for the preparation of a series of 2,3-disubstituted-quinazolin-4(3H) -ones is described via a three step reaction from anthranilic acid. The obtained results also reveal that microwave-assisted rapid decomposition of formamide under controlled conditions of power, temperature and time is a very convenient source of ammonia for the synthesis of 2-substituted-quinazolin-4(3H)-ones and other rings. (c) 2007 Elsevier Ltd. All rights reserved.
• Malhotra, S.; Koul, S. K.; Sharma, R. L., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 937 - 940
  作者：Malhotra, S.、Koul, S. K.、Sharma, R. L.、Anand, K. K.、Gupta, O. P.、Dhar, K. L.

  DOI：——

  日期：——
• Distinct novel quinazolinone exhibits selective inhibition in MGC-803 cancer cells by dictating mutant p53 function
  作者：Guo-Hai Zhang、Wen-Bin Xue、Yun-Feng An、Jing-Mei Yuan、Jiang-Ke Qin、Cheng-Xue Pan、Gui-Fa Su

  DOI：10.1016/j.ejmech.2015.03.053

  日期：2015.5

  The mutant p53 proteins and their corresponding cellular response can be manipulated by novel quinazolinone derivatives 4-8 (a-i) in p53 mutant cancer cells. Of the two most potent compounds, 4a exhibited promising broad-spectrum anti-cancer effects, whereas 6c showed selective and exclusive inhibition activity in p53 mutant cancer cell lines but low toxicity to wild-type p53 cancer cell A375 and normal lung fibroblast WI-38 cells. Furthermore, 6c exhibited a more sophisticated mechanism for celldestructive response by causing S/G2 phase arrest effect and cell size reduction. Compared with the cellular response of 6b and genetic background of cell lines studied, p53 mutation was found to be the key factor and main target for 6c evoked cell-destructive response. Molecular mechanism studies indicated that p53 phosphorylation and acetylation dual-targeting inhibitor 6c exerted anti-cancer activities with a special mechanism in evoking cell apoptosis by arresting mutant p53 function to trigger the deregulation of Cdk2 caused Bim-mediated apoptosis. To the best of our knowledge, 6c is the first quinazolinone derivative to dictate mutant p53 function for apoptotic cell death. (C) 2015 Elsevier Masson SAS. All rights reserved.