3-{[(4-hydroxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one | 56158-77-1

• 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-{[(4-hydroxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one
• 英文别名: 3-[(4-hydroxybenzylidene)amino]-2-phenyl-3H-quinazolin-4-one；3[(4-hydroxybenzylidene)amino]-2-phenyl-3H-quinazolin-4-one；3-(4-hydroxy-benzylideneamino)-2-phenyl-3H-quinazolin-4-one；3[(4-Hydroxybenzylidene)-amino]-2-phenyl-3h-quinazolin-4-one；3-[(4-hydroxyphenyl)methylideneamino]-2-phenylquinazolin-4-one
• CAS: 56158-77-1
• 化学式: C₂₁H₁₅N₃O₂
• 分子量: 341.369
• InChiKey: SPRPCTDAERTWHA-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  561.7±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  65.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-{[(4-hydroxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以75%的产率得到3-[(4-ethoxybenzylidene)amino]-2-phenyl-3H-quinazolin-4-one
  参考文献：
  名称：

  一些新型喹唑啉-4-(3H)-酮类抗惊厥和抗抑郁药的设计与合成

  摘要：

  3-氨基-2-苯基-1H-喹唑啉-4反应合成了一系列3-[(4-取代-苯亚甲基)-氨基]-2-苯基-3H-喹唑啉-4-酮(5a-k) -一种与对羟基苯甲醛，然后进一步与各种烷基/苄基卤化物或取代苯甲酰溴化物。化合物的结构经IR、NMR、MS和元素分析确证。使用 MES 和 scPTZ 测试评估抗惊厥活性。通过强制游泳池试验评估了一些选定化合物的抗抑郁活性。化合物 3-[(4-butoxy-benzylidene)-amino]-2-phenyl-3H-quinazolin-4-one 成为最有前途的抗惊厥药，没有任何运动损伤作用。

  DOI：

  10.1007/s12272-013-0004-y
• 作为产物：
  描述：

  methyl 2-(benzamido)benzoate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 3-{[(4-hydroxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis, Antimicrobial and Anticancer Evaluation of 2-Azetidinones Clubbed with Quinazolinone

  摘要：

  使用邻氨基苯甲酸合成了2-氮杂环丁酮与喹唑啉酮的系列新化合物。对所有合成的化合物进行了评估，以确定其对两种革兰氏阳性细菌（枯草芽孢杆菌和金黄色葡萄球菌）、一种革兰氏阴性细菌（大肠杆菌）和两种真菌（白色念珠菌和黑曲霉）的抗菌活性。还对所有合成的化合物进行了筛选，以确定其对人类乳腺癌细胞系MCF-7的抗癌活性。抗菌和抗癌研究结果表明，化合物12和5（IC50 = 49.52 μM）分别是最强的抗菌剂和抗癌剂。

  DOI：

  10.1007/s11094-016-1392-3

文献信息

• Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones
  作者：Krishnan Suresh Kumar、Swastika Ganguly、Ravichandran Veerasamy、Erik De Clercq

  DOI：10.1016/j.ejmech.2010.07.058

  日期：2010.11

  3-(benzylideneamino)-2-phenylquinazoline-4(3H)-ones were prepared through Schiff base formation of 3-amino-2-phenyl quinazoline-4(3)H-one with various substituted carbonyl compounds. Their chemical structures were elucidated by spectral studies. Cytotoxicity and antiviral activity were evaluated against herpes simplex virus-1 (KOS), herpes simplex virus-2 (G), vaccinia virus, vesicular stomatitis virus,

  通过席夫碱与各种取代的羰基化合物形成3-氨基-2-苯基喹唑啉-4(3)H-酮，制备了一系列新的3-(亚苄基氨基)-2-苯基喹唑啉-4(3H)-酮。通过光谱研究阐明了它们的化学结构。针对单纯疱疹病毒-1 (KOS)、单纯疱疹病毒-2 (G)、牛痘病毒、水疱性口炎病毒、单纯疱疹病毒-1 TK-KOS ACVr、副流感病毒-3病毒、呼肠孤病毒-评估细胞毒性和抗病毒活性1、辛德比斯病毒、柯萨奇病毒B4、蓬塔托罗病毒、猫冠状病毒（FIPV）、猫疱疹病毒、呼吸道合胞病毒、甲型H1N1流感亚型、甲型H3N2流感亚型和乙型流感病毒。化合物2a对整个测试病毒显示出更好的抗病毒活性。
• Antibacterial Activity of Some 3-(Arylideneamino)-2-phenylquinazoline-4(3H)-ones: Synthesis and Preliminary QSAR Studies
  作者：Ashis Nanda、Subarna Ganguli、Ranadhir Chakraborty

  DOI：10.3390/12102413

  日期：——

  Synthesis of ten 3-(arylideneamino)-2-phenylquinazoline-4(3H)-ones is reported. All the compounds contained a common phenyl group at the 2-position, while the substituents on the arylideneamino group were varied. The compounds were investigated for their antimicrobial activity against both Gram-positive (Staphylococcus aureus 6571 and Bacillus subtilis) and Gram-negative bacteria (Escherichia coli

  报道了十个 3-(亚芳基氨基)-2-苯基喹唑啉-4(3H)-ones 的合成。所有化合物在 2 位都含有一个共同的苯基，而亚芳基氨基上的取代基是不同的。使用浊度测定法研究了这些化合物对革兰氏阳性菌（金黄色葡萄球菌 6571 和枯草芽孢杆菌）和革兰氏阴性菌（大肠杆菌 K12 和痢疾志贺氏菌 6）的抗菌活性。发现3-亚芳基氨基取代基的掺入增强了喹唑酮系统的抗菌活性。初步的 QSAR 研究是使用一些计算机衍生的属性描述符、分配系数的计算值以及通常的哈米特西格玛常数和取代基的摩尔折射率来完成的。
• Quinazolinone Platinum Metal Complexes: in silico Design, Synthesis and Evaluation of Anticancer Activity
  作者：Sanjay D. Sawant、Megha Sahu、Amit G. Nerkar

  DOI：10.14233/ajchem.2018.21330

  日期：——

  Dihydrofolate reductase (DHFR) has been explored as a target for the development of agents for wide variety of human diseases, including cancer, autoimmune and infectious diseases. Several metal complexes are being used in management of cancer. The square planar Pt(II) complex, cis PtCl2(NH3)2 turned out to be even more effective at forcing filamentous growth. Cisplatin is an inorganic heavy metal complex that has activity similar to cell-cycle-phase-nonspecific alkylating agents such as cyclophosphamide and some other Ni and Cu metal complexes. It produces intrastrand DNA cross-link and form DNA adducts, thus inhibiting the synthesis of DNA, RNA and proteins preferentially. in silico Screening of platinum metal complexes was performed by Vlife MDS 4.3 software. In this procedure, selection of molecule, selection of PDB, optimization of PDB and docking of molecules was carried out. Synthesis of metal complexes was done by multi component reaction method. Platinum metal complexes of quinazolinone Schiff bases prioritized by in silico studies were characterized by IR, TLC, NMR, XRD, FESEM and some physico-chemical parameters. Prioritized molecules were further evaluated by in vitro anticancer cell line assay on ten cell lines with adriamycin as standard. The results showed that the platinum metal complexes of qunazolinone Schiff bases can be potential anticancer agents through DHFR inhibitory mechanism.

  二氢叶酸还原酶（DHFR）已被视为一种靶标，用于开发治疗各种人类疾病（包括癌症、自身免疫性疾病和传染性疾病）的药物。有几种金属复合物正被用于治疗癌症。方形平面铂（II）复合物顺式 PtCl2(NH3)2 在强迫丝状生长方面更为有效。顺铂是一种无机重金属复合物，其活性类似于细胞周期阶段非特异性烷化剂，如环磷酰胺和其他一些镍和铜金属复合物。它能产生链内 DNA 交联并形成 DNA 加合物，从而优先抑制 DNA、RNA 和蛋白质的合成。铂金属复合物的筛选是通过 Vlife MDS 4.3 软件进行的。筛选过程包括分子选择、PDB 选择、PDB 优化和分子对接。金属配合物的合成采用多组分反应法。通过 IR、TLC、NMR、XRD、FESEM 和一些物理化学参数对硅学研究优先考虑的喹唑啉酮席夫碱铂金属配合物进行了表征。以阿霉素为标准，对十种细胞系进行了体外抗癌细胞系测定，进一步评估了优先分子。结果表明，坤唑啉酮席夫碱的铂金属配合物可以通过 DHFR 抑制机制成为潜在的抗癌剂。
• Husain, M. I.; Shukla, Sarveshwar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 545 - 548
  作者：Husain, M. I.、Shukla, Sarveshwar

  DOI：——

  日期：——
• Synthesis, spectroscopic characterization, antineoplastic, <i>in vitro</i>-cytotoxic, and antibacterial activities of mononuclear ruthenium(II) complexes
  作者：Sreekanth Thota、Mohammad Imran、Manasa Udugula、Subhas Somalingappa Karki、Narasimha Kanjarla、Rajeshwar Yerra、Jan Balzarini、Erik De Clercq

  DOI：10.1080/00958972.2012.663082

  日期：2012.3.10

  The synthesis, antineoplastic, cytotoxic, and antibacterial activities of Ru(II) complexes derived from quinazoline and thiosemicarbazone ligands are reported. These complexes have been prepared and characterized by UV-Vis, IR, H-1-NMR, FAB-mass spectroscopy, and elemental analysis. The ligands and resulting complexes were subjected to in vivo antineoplastic activity against a transplantable murine tumor cell line Ehrlich ascites carcinoma (EAC) and in vitro cytotoxic activity against human cancer cell line Molt 4/C-8, CEM, and murine tumor cell line L 1210. The ruthenium complexes show promising biological activity especially in decreasing tumor volume and viable ascitic cell counts. These complexes prolonged the life span of mice bearing EAC tumors by 10-52%. In vitro evaluation of these ruthenium complexes revealed cytotoxic activity from 0.29 to 2.9 mu mol L-1 against Molt 4/C-8, 0.22 to 2.1 mu mol L-1 against CEM and 0.42 to 4.7 mu mol L-1 against L1210 cell proliferation, depending on the nature of the compound. The metal complexes are more active than the parent ligand and exhibit mild to moderate antibacterial activity.