2-肼基-3-苯基喹唑啉-4-酮 | 731-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-肼基-3-苯基喹唑啉-4-酮
• 英文名称: 2-hydrazino-3-phenyl-3H-quinazolin-4-one
• 英文别名: 2-hydrazino-3-phenylquinazolin-4(3H)-one；2-hydrazinyl-3-phenylquinazolin-4(3H)-one；2-hydrazinyl-3-phenylquinazolin-4-one
• CAS: 731-52-2
• 化学式: C₁₄H₁₂N₄O
• mdl: MFCD00614682
• 分子量: 252.275
• InChiKey: VNBHFDXTDVKBRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-肼基-3-苯基喹唑啉-4-酮 在 一水合肼 作用下， 以 异丙醇 、 正丁醇 为溶剂， 反应 16.0h， 生成 3-氨基-2-肼基喹唑啉-4-酮
  参考文献：
  名称：

  Kottke; Kuhmstedt; Grafe, Pharmazie, 1990, vol. 45, # 1, p. 30 - 33

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(乙硫基)-3-苯基喹唑啉-4(3H)-酮 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-肼基-3-苯基喹唑啉-4-酮
  参考文献：
  名称：

  Spectral Characterization of Novel 3-Phenyl-2-Substituted Quinazoline and Fused Quinazoline Derivatives

  摘要：

  3-phenyl-2-thioxo-quinazolin-4(3H)one 1 was utilized for the construction of some novel 2-substituted quinazolin-4(3H)one derivatives through the formation of 2-hydrazinyl quinazolinone, which was used as the key starting material for the synthesis of 2-heteryl quinazolines via the reaction with one carbon donors, -diketones and -ketoester. Infrared, H-1 NMR, and mass spectra of the synthesized compounds were discussed. Some of them showed promising anti-inflammatory activity. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.642924

文献信息

• Synthesis and pharmacological investigation of novel 1-substituted-4-phenyl-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-ones as a new class of H1-antihistaminic agents
  作者：Veerachamy Alagarsamy、Rajani Giridhar、Mangai Ram Yadav

  DOI：10.1016/j.bmcl.2005.02.016

  日期：2005.4

  A series of novel 1-substituted-4-phenyl-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-ones 7 were synthesized by the cyclization of 2-hydrazino-3-phenylquinazolin-4(3H)-one 6 with various one carbon donors. The starting material 2-hydrazino-3-phenylquinazolin-4(3H)-one 6, was synthesized from aniline 1 by a novel innovative route. When tested for their in vivo H(1)-antihistaminic activity on conscious guinea

  通过2-肼基-3-苯基喹唑啉-4的环化反应合成了一系列新型的1-取代的4-苯基-1,2,4-三唑并[4,3-a]喹唑啉-5（4H）-ones 7。 （3H）-具有各种一个碳供体的一6。原料2-肼基-3-苯基喹唑啉-4（3H）-一6是通过一种新颖的创新路线从苯胺1合成的。当测试其对有意识的豚鼠的体内H（1）-抗组胺活性时，所有测试化合物均能显着保护动物免受组胺诱导的支气管痉挛，而化合物1-甲基-4-苯基-1,2,4-三唑并[4]发现3-3-]喹唑啉-5（4H）-1 7b（保护百分比为70.7％）与参考标准马来酸氯苯那敏（保护百分比为71％）等价。与参考标准品（26％）相比，这些化合物的镇静作用微不足道（约5％）。
• Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents
  作者：V. Alagarsamy、V. Raja Solomon、K. Dhanabal

  DOI：10.1016/j.bmc.2006.09.065

  日期：2007.1.1

  were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. While the test compounds exhibited significant activity, compounds, 2-(N'-2-butylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS1), 2-(N'-3-pentylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS2) and 2-(N'-2-pentylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS3), exhibited moderate analgesic activity. The compound

  通过使2-肼基-3-苯基-3H-喹唑啉-4-酮的氨基与不同的醛和酮反应，合成了多种新颖的3-苯基-2-取代-3H-喹唑啉-4-酮。由苯胺合成起始原料2-肼基-3-苯基-3H-喹唑啉-4-酮。研究了标题化合物的镇痛，抗炎和致溃疡指数活性。尽管测试化合物显示出显着的活性，但化合物2-（N'-2-亚丁基-肼基）-3-苯基-3H-喹唑啉-4-酮（AS1），2-（N'-3-亚戊基-肼基） -3-苯基-3H-喹唑啉-4-酮（AS2）和2-（N'-2-亚戊基-肼基）-3-苯基-3H-喹唑啉-4-酮（AS3）表现出中等的镇痛活性。化合物2-（N' 与参考标准双氯芬酸钠相比，-2-亚戊基-肼基）-3-苯基-3H-喹唑啉-4-酮（AS3）显示出更强的抗炎活性。有趣的是，与阿司匹林相比，受试化合物仅显示出轻度的致溃疡性副作用。
• Tautomerism of guanidines studied by 15N NMR: 2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compounds
  作者：Ion Ghiviriga、Bahaa El-Dien M. El-Gendy、Peter J. Steel、Alan R. Katritzky

  DOI：10.1039/b907577a

  日期：——

  2-Hydrazono-3-phenylquinazolin-4(3H)-ones 11a–i are shown by 15N NMR to exist in DMSO solution predominantly as the imino tautomers B and not the amino tautomers A. 2-Hydrazino-benzimidazole derivative 12 and 2-hydrazino-4,6-dimethylpyrimidine derivative 13 were found to exist predominantly as the amino tautomers.

  2-肼叉-3-苯基喹唑啉-4(3H)-酮11a–i在DMSO溶液中主要以亚胺互变异构体B存在，而不是氨基互变异构体A，这一结论通过15N NMR得以证实。而2-肼基苯并咪唑衍生物12和2-肼基-4,6-二甲基嘧啶衍生物13则主要以氨基互变异构体形式存在。
• Anti-HIV, Antitubercular and Antibacterial Activities of Novel 3-(Substituted Quinazolinylamino)-2-phenyl quinazolin-4(3H)ones
  作者：M.T. Sulthana、K. Chitra、V. Alagarsamy

  DOI：10.14233/ajchem.2020.22280

  日期：2020.1.15

  exhibited the antitubercular activity with the MIC of 25 μg/mL and anti-HIV activity with the MIC of 35.4 μg/mL against HIV1 and HIV2 and offers potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities

  在本研究中，我们通过3-(取代)-2-肼基喹唑啉-4(3H)-酮的反应合成了一系列新型2-苯基-3-(取代喹唑啉氨基)喹唑啉-4(3H)-酮与2-苯基-3,1-苯并恶嗪-4-酮。由各种伯胺合成起始材料3-(取代)-2-肼基喹唑啉-4(3H)-酮。采用琼脂稀释法筛选所有合成化合物的抗结核、抗HIV和针对不同革兰氏阳性和革兰氏阴性菌株的抗菌活性。受试化合物中，3-(4-硝基苯基)-2-(4-氧代-2-苯基喹唑啉-3(4H)-基氨基)喹唑啉-4(3H)-酮(BQZ6)和3-(4-氯苯基) -2-(4-oxo-2-苯基喹唑啉-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ7) 对大肠杆菌、铜绿假单胞菌和金黄色葡萄球菌具有最强的 MIC 抗菌活性3微克/毫升。化合物BQZ7对HIV1和HIV2表现出抗结核活性（MIC为25 μg/mL）和抗HIV活性（MIC为35.4
• A new convenient synthesis of 2,4-disubstituted-1,2,4-triazolo[1,5-<i>a</i>] quinazolin-5(4<i>H</i>)-ones
  作者：Ahmad S. Shawali、Hamdi M. Hassaneen、Nabil Kh. Shurrab

  DOI：10.1002/jhet.5570450642

  日期：2008.11

  A novel series of 2,4-disubstituted-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-ones were prepared by Dimroth rearrangement of their respective isomers namely 1,4-disubstituted-[1,2,4]triazolo[4,3-a]-quinazolin-5(4H)-ones. The latter were prepared via new synthetic strategy based on 1,5-elecrocyclization of the respective N-(4-oxo-3-phenylquinazolin-2-yl)nitrilimines.

  通过Dimroth重排它们各自的异构体即1,4-二取代-[[ ] ，制备了一系列新的2,4-二取代-1,2,4-三唑并[1,5- a ]喹唑啉-5（4 H）-酮。 1,2,4]三唑并[4,3 - a ]-喹唑啉-5（4 H）-ones。后者通过基于各自的N-（4-氧代-3-苯基喹唑啉-2-基）硝苯胺的1，5-电子环化的新合成策略制备。