4-(4-氧代-2-苯基喹唑啉-3-基)苯甲酸 | 37856-24-9

• 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: 4-(4-氧代-2-苯基喹唑啉-3-基)苯甲酸
• 英文名称: 4-(4-oxo-2-phenylquinazolin-3(4H)-yl)benzoic acid
• 英文别名: Benzoic acid, 4-(4-oxo-2-phenyl-3(4H)-quinazolinyl)-；4-(4-oxo-2-phenylquinazolin-3-yl)benzoic acid
• CAS: 37856-24-9
• 化学式: C₂₁H₁₄N₂O₃
• 分子量: 342.354
• InChiKey: UDCJFVPZPKUZGM-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C(Solv: ethanol (64-17-5))
• 沸点：
  585.3±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氧代-2-苯基喹唑啉-3-基)苯甲酸 在 氯化亚砜 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 potassium 2-{[4-(4-oxo-2-phenylquinazoline-3(4H)-yl) phenyl]carbonyl}hydrazine carbodithioate
  参考文献：
  名称：

  Synthesis, characterization, and antimicrobial studies of novel 1,3,4-thiadiazolium-5-thiolates

  摘要：

  Sixteen novel thiadiazolium derivatives 6(a-h) and 12(a-h) were synthesized by conventional route starting from anthranilic acid using different acid chloride derivatives. The structure of all the newly synthesized compounds was established by IR, NMR, mass spectroscopy, and elemental analysis. The compounds were also screened for their antibacterial activity against some important bacterial species. Some of the compounds were found excellent active against these species.

  DOI：

  10.1007/s00044-011-9632-2
• 作为产物：
  描述：

  苯甲酰氯 以 吡啶 为溶剂， 反应 6.0h， 生成 4-(4-氧代-2-苯基喹唑啉-3-基)苯甲酸
  参考文献：
  名称：

  Synthesis and Antiviral Activities of Some 2,3-Disubstituted Quinazoline Derivatives

  摘要：

  在寻找新型有效抗病毒药物的过程中，合成了2,3-二取代喹唑啉衍生物，并测试了其抗病毒活性。对氨基苯甲酸（1）在吡啶中与芳香酸酰氯反应得到2-芳基-4-氧代-3H-苯并噁嗪（2），后者再与对氨基苯甲酸（PABA）反应生成2-芳基-3-对羧基苯基-4-氧代-3H-喹唑啉（3）。化合物3在浓硫酸存在下进一步与酰胺醇反应，生成3-[苯甲酸-(3-邻苯二甲酰亚胺甲基/3-乙基-3H-2-苯基-4-氧代喹唑啉基/1-乙基-7-羟基-4-甲基-2-氧代喹啉基)]-2-芳基-3H-喹唑啉-4-酮（4）。合成的化合物4a-f已对对体外和体内抗日本脑炎病毒（JEV）和I型单纯疱疹病毒（HSV-I）进行了评价。所合成的化合物通过物理和化学分析进行了表征。获得的结果可作为构建新型化学实体的关键步骤，与标准药物相比具有有趣的抗病毒活性。

  DOI：

  10.14233/ajchem.2015.19132

文献信息

• Synthesis, In Silico and In Vitro Assessment of New Quinazolinones as Anticancer Agents via Potential AKT Inhibition
  作者：Ahmed A. Noser、Mohamed El-Naggar、Thoria Donia、Aboubakr H. Abdelmonsef

  DOI：10.3390/molecules25204780

  日期：——

  A series of novel quinazolinone derivatives (2–13) was synthesized and examined for their cytotoxicity to HepG2, MCF-7, and Caco-2 in an MTT assay. Among these derivatives, compounds 4 and 9 exhibited significant cytotoxic activity against Caco-2, HepG2, and MCF-7 cancer cells. Compound 4 had more significant inhibitory effects than compound 9 on Caco-2, HepG2, and MCF-7 cell lines, with IC50 values

  合成了一系列新型喹唑啉酮衍生物 (2-13)，并在 MTT 试验中检测了它们对 HepG2、MCF-7 和 Caco-2 的细胞毒性。在这些衍生物中，化合物 4 和 9 对 Caco-2、HepG2 和 MCF-7 癌细胞表现出显着的细胞毒活性。化合物4对Caco-2、HepG2和MCF-7细胞系的抑制作用比化合物9更显着，IC50值分别为23.31±0.09、53.29±0.25和72.22±0.14μM。AKT 通路是人类癌症最常见的失调信号之一。AKT 在人类癌症中也过度表达，例如神经胶质瘤、肺癌、乳腺癌、卵巢癌、胃癌和胰腺癌。进行分子对接研究以分析新合成的喹唑啉酮衍生物对智人 AKT1 蛋白的抑制作用。发现分子对接模拟符合体外研究，因此支持生物活性。结果表明，如对接研究所述，化合物 4 和 9 可通过其对 AKT1 的潜在抑制作用作为癌症治疗的候选药物。
• Synthesis, characterization and biological activity of new 3(4H)-quinazolinone derivatives
  作者：A. I. El-Shenawy

  DOI：10.1134/s1070363217090237

  日期：2017.9

  synthesis of many heterocyclic systems. Ethyl 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate 2 upon reaction with hydrazine hydrate gave 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate benzoylhydrazide 3. Compound 3 on treatment with 3-nitrobenzaldehyde, acetyl acetone, ethyl acetoacetate, and ammonium thiocyanate yielded compounds 4–8, respectively. Isothiocyanate 8 was used for the synthesis of other

  喹唑啉基苯甲酸1被用作许多杂环系统合成的前体。与水合肼反应后的4- [4-氧代-2-苯基喹唑啉-3（4 H）-基]苯甲酸乙酯2得到4- [4-氧代-2-苯基喹唑啉-3（4 H）-基]苯甲酸乙酯苯甲酰肼3。化合物3治疗与3-硝基苯甲醛，乙酰丙酮，乙酰乙酸乙酯，和硫氰酸铵，得到化合物4 - 8，分别。异硫氰酸盐8用于合成其他喹唑啉衍生物9 – 16通过与各种试剂的反应。所有新合成的喹唑啉酮衍生物均已通过1 H NMR，IR和质谱表征。对大多数合成产品的抗菌和抗真菌活性进行了评估，其中一些具有高活性。
• Dash, B.; Dora, E. K.; Panda, C. S., Journal of the Indian Chemical Society, 1980, vol. 57, # 8, p. 835 - 836
  作者：Dash, B.、Dora, E. K.、Panda, C. S.

  DOI：——

  日期：——
• Synthesis and anticonvulsant activity of novel quinazolin-4(3H)-one derived pyrazole analogs
  作者：Veerachamy Alagarsamy、Govindaraj Saravanan

  DOI：10.1007/s00044-012-0169-9

  日期：2013.4

  Eighteen novel 6,8-(dibromo/unsubstituted)-2-(methyl/phenyl)-3-(4-(5-(substitutedphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl)phenyl)-quinazolin-4(3H)-ones 4a-4r were designed and synthesized in good yield. Antiepileptic screening of the title compounds was performed using MES and scPTZ seizures tests while the neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 4d, 4e, 4p, 4q, and 4r were found active in MES model, while 4a, 4d, 4f, 4m, and 4p showed significant antiepileptic activity in scPTZ model. Further, all these eight compounds were administered to rats and compounds 4e, 4p, and 4q showed better activity than Phenytoin in oral route. Among these compounds 4p revealed protection in MES after i.p. administration at a dose of 30 mg/kg (0.5 h) and 100 mg/kg (4 h). The compound 4p also provided protection in the scPTZ at a dose of 100 mg/kg (0.5 h) and 300 mg/kg (4 h).
• Pandey; Pathak; Mishra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1940 - 1943
  作者：Pandey、Pathak、Mishra

  DOI：——

  日期：——