3-(4-硝基苯基)-2-硫代-2,3-二氢-1H-喹唑啉-4-酮 | 72176-80-8

• 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: 3-(4-硝基苯基)-2-硫代-2,3-二氢-1H-喹唑啉-4-酮
• 英文名称: 3-(4-nitrophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 3-(4-nitrophenyl)-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 72176-80-8
• 化学式: C₁₄H₉N₃O₃S
• mdl: MFCD02380578
• 分子量: 299.31
• InChiKey: IINOGTDZSDDTSV-UHFFFAOYSA-N

物化性质

• 熔点：
  319-320

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯基)-2-硫代-2,3-二氢-1H-喹唑啉-4-酮 在 potassium carbonate 、 sodium hydroxide 、 肼 作用下， 以 乙醇 为溶剂， 反应 37.0h， 生成 2-(3-(4-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-dione
  参考文献：
  名称：

  Anti-HIV and Antibacterial Activities of Novel 2-(3-Substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones

  摘要：

  synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different gram positive and gram negative strains by agar dilution method. Among the test compounds, 2-(3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-dione (QCT7) shown most potent antibacterial activity against E. coli , and S. aureus with the MIC of 3 µg/mL. The compound

  DOI：

  10.1134/s1068162021010246
• 作为产物：
  描述：

  4-硝基苯基二硫代氨基甲酸甲酯 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 3-(4-硝基苯基)-2-硫代-2,3-二氢-1H-喹唑啉-4-酮
  参考文献：
  名称：

  Anti-HIV and Antibacterial Activities of Novel 2-(3-Substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones

  摘要：

  synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different gram positive and gram negative strains by agar dilution method. Among the test compounds, 2-(3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-dione (QCT7) shown most potent antibacterial activity against E. coli , and S. aureus with the MIC of 3 µg/mL. The compound

  DOI：

  10.1134/s1068162021010246

文献信息

• 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
• Synthesis, in vitro, and in silico studies of newly functionalized quinazolinone analogs for the identification of potent α-glucosidase inhibitors
  作者：Hayat Wali、Ayaz Anwar、Shahbaz Shamim、Khalid Mohammed Khan、Mohammad Mahdavi、Uzma Salar、Bagher Larijani、Shahnaz Perveen、Muhammad Taha、Mohammad Ali Faramarzi

  DOI：10.1007/s13738-021-02159-2

  日期：2021.8

  Functionalized quinazolinone derivatives 1–30 were synthesized by two-step reaction. First, anthranilic acid was treated with substituted phenyl isothiocyanate to synthesize 3-aryl-2-thioxo-2,3-dihydroquinazolinone derivatives 1–8 which in turn reacted with different bromoacetophenone derivatives to obtain fully functionalized quinazolinone derivatives 9–30. Both reactions were catalyzed by triethylamine. All the products were characterized by EI-, HREI-MS, 1H-, and 13CNMR spectroscopic techniques. All compounds were subjected to their in vitro α-glucosidase inhibitory activity. Results showed that except compound 1–3, 5, 7, and 22, all compounds were found potent and showed many folds increased α-glucosidase enzyme inhibition as compared to standard acarbose (IC50 = 750.0 ± 10.0 µM). Compound 13 (IC50 = 85.0 ± 0.5 µM) was recognized as the most potent analog of the whole series, with ninefold enhanced inhibitory potential than the standard acarbose. Compounds 1–9, 11, 12, 22, and 26 were structurally known compounds, while remaining all are new. Kinetic study on compound 13 showed that the compound is following a competitive-type inhibition mechanism. Furthermore, in silico studies have also been performed to better rationalize the interactions between synthetic compound and active site of the enzyme.

  通过两步反应合成了功能化的喹唑啉酮衍生物1-30。首先，用取代的苯基异硫氰酸酯处理邻氨基苯甲酸，合成3-芳基-2-硫代-2,3-二氢喹唑啉酮衍生物1-8，然后这些衍生物与不同的溴乙酰苯衍生物反应，得到完全功能化的喹唑啉酮衍生物9-30。两种反应都由三乙胺催化。所有产物都通过EI-、HREI-MS、1H-和13CNMR光谱技术进行表征。所有化合物都进行了体外α-葡萄糖苷酶抑制活性测试。结果显示，除了化合物1-3、5、7和22外，所有化合物都表现出较强的活性，并且相比于标准药物阿卡波糖（IC50 = 750.0 ± 10.0 µM），它们的α-葡萄糖苷酶酶抑制作用提高了许多倍。化合物13（IC50 = 85.0 ± 0.5 µM）被认为是整个系列中最强的类似物，其抑制潜力比标准阿卡波糖提高了九倍。化合物1-9、11、12、22和26是已知结构的化合物，其余所有都是新化合物。对化合物13的动力学研究表明，该化合物遵循竞争性抑制机制。此外，还进行了计算机模拟研究，以更好地合理化合成化合物与酶活性位点之间的相互作用。
• Design, synthesis, antiproliferative and antibacterial evaluation of quinazolinone derivatives
  作者：Hai-Xin Wang、Hai-Ying Liu、Wei Li、Shuai Zhang、Zheng Wu、Xin Li、Cai-Wen Li、Yu-Ming Liu、Bao-Quan Chen

  DOI：10.1007/s00044-018-2276-8

  日期：2019.2

  A series of novel quinazolinone derivatives bearing a disulfide bond were designed and synthesized. Their in vitro antiproliferative activities were evaluated using CCK-8 assay against SMMC-7721, Hela, A549 and MCF-7 human cancer cell lines and normal cell lines L929. The preliminary bioassay results demonstrated that all compounds 7a–7h, 8a–8h and 9a–9h exhibited antiproliferation with various degrees

  设计并合成了一系列带有二硫键的新型喹唑啉酮衍生物。使用针对SMMC - 7721，Hela，A549和MCF - 7人癌细胞系和正常细胞系L929的CCK - 8分析评估了它们的体外抗增殖活性。初步的生物测定结果表明，所有化合物7a – 7h，8a – 8h和9a – 9h均表现出不同程度的抗增殖作用，并且某些化合物对不同癌细胞株显示出比阳性对照5-氟尿嘧啶更好的效果。在这些化合物中，8c和9f对SMMC-7721细胞显示出显着的抗增殖活性，IC 50值分别为2.88和2.56μM。在Hela细胞中，化合物9c和9d表现出高度有效的生物学活性，IC 50值分别为3.16和2.68μM。化合物7a和9a对A549细胞表现出良好的抑制作用，IC 50值分别为3.53和3.54μM。在MCF-7细胞中，化合物7e，8e和9e对IC 50表现出出色的活性分别为1.26、1.12和1.85μM。此外
• Facile Route for Novel Quinazolinone-Fused Azauracils through Cyclodesulfurization of Thioquinazolinones
  作者：Vinod Tiwari、Raju Kale、Virendra Prasad

  DOI：10.1055/s-0030-1259301

  日期：2011.1

  An efficient, novel, short, and high-yielding one-pot protocol for the synthesis of diverse quinazolinone-fused azauracil heterocycles through cyclodesulfurization and intramolecular cyclization of thioquinazolinone using silver cyanate is described.

  本文描述了一种高效、新颖、简便且高产的一锅法，用银氰酸盐通过环脱硫和硫喹唑啉酮的分子内环化合成多样的喹唑啉酮融合的氮杂尿嘧啶杂环。
• Design and synthesis of novel quinazolinone‐based fibrates as PPARα agonists with antihyperlipidemic activity
  作者：Rasha M. Hassan、Islam H. Ali、Mohammed S. Abdel‐Maksoud、Heba M. I. Abdallah、Ahmed M. El Kerdawy、Francesca Sciandra、Iman A. Y. Ghannam

  DOI：10.1002/ardp.202100399

  日期：2022.3

  discover new antihyperlipidemic agents, a new set of quinazolinone-fibrate hybrids 9a–r bearing the essential features for peroxisome proliferator-activated receptor-α (PPARα) agonistic activity was synthesized and the structures were confirmed by different spectral data. All the target compounds were screened for their PPARα agonistic activity. Compounds 9o and 9q exhibited potent activity, with EC50

  为了发现新的抗高血脂药物，合成了一组具有过氧化物酶体增殖物激活受体-α (PPARα) 激动活性的基本特征的新型喹唑啉酮-贝特杂化物 9a-r ，并通过不同的光谱数据证实了其结构。筛选所有目标化合物的 PPARα 激动活性。化合物9o和9q表现出强效活性，EC 50值分别比非诺贝特高 8.7 倍和 27 倍。对PPARα受体活性位点中所有新合成的化合物进行分子对接研究，以研究它们在受体中的相互作用和能量。此外，使用 Triton WR-1339 诱导的高脂血症大鼠测定了化合物9o和9q的抗高脂血症和抗氧化活性。化合物9q以剂量依赖性方式表现出有效的降血脂活性，显着降低血清总胆固醇、甘油三酯、低密度脂蛋白胆固醇和极低密度脂蛋白胆固醇水平，并增加高密度脂蛋白胆固醇水平。此外，它具有强大的抗氧化特性，显着提高了还原型谷胱甘肽的水平以及总抗氧化能力，并显着降低了丙二醛水平。组织病理学研究表明，化合