3-(4- hydroxybenzylideneamino)-2-methylquinazolin-4(3H)-one | 41332-41-6

• 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- hydroxybenzylideneamino)-2-methylquinazolin-4(3H)-one
• 英文别名: 3-((4-Hydroxybenzylidene)amino)-2-methylquinazolin-4(3h)-one；3-[(4-hydroxyphenyl)methylideneamino]-2-methylquinazolin-4-one
• CAS: 41332-41-6
• 化学式: C₁₆H₁₃N₃O₂
• mdl: MFCD00602933
• 分子量: 279.298
• InChiKey: KSARCODDNODDAY-UHFFFAOYSA-N

物化性质

• 熔点：
  210-214 °C(Solv: ethanol (64-17-5))
• 沸点：
  490.9±47.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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- hydroxybenzylideneamino)-2-methylquinazolin-4(3H)-one 在 溴 、 溶剂黄146 作用下， 以55%的产率得到2-(bromomethyl)-3-((4-hydroxybenzylidene)amino)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of newer quinazolin-4-one derivatives

  摘要：

  2-Methyl-3-aminosubstituted-3H-quinazolin-4-ones (1-2), 2-methyl-3-(substituted-arylidene-amino)-substituted-3H-quinazolin-4-ones (3-10), 2-bromomethyl-3-(substituted-arylidene-amino)-substituted-3H-quinazolin-4-ones (11-18), 2-(5'-pyridin-4-yl-[1,3,4]-oxadiazol-2-yl-sulfanylmethyl)-3-(substituted-arylidene-amino)-substituted-3H-quinazolin-4-ones (19-26), 3-(3-chloro-2-oxo-4-substituted-aryl-azetidin-1-yl)-2-(5-pyridin-4-yl-[1,3,4]-oxadiazol-2-yl-sulfanylmethyl)-substituted-3H-quinazolin-4-ones (27-34) and 3-(4-oxo-2-substituted-aryl-thiazolidin-3-yl)-2-(5-pyridin-4-yl-[1,3,4]-oxadiazol-2-yl-sulfanylmethyl)-substituted-3H-quinazolin-4-ones (35-42) were synthesized in present study. All the compounds exhibited anti-inflammatory activity at the dose 50 mg/kg p.o. varying degree from 16.3 to 36.3% inhibition of oedema. Compound 40 showed same activity at 25, 50 and 100 mg/kg p.o. like standard drugs. The structure of all these newly synthesized compounds was confirmed by their analytical (C, H, N) and spectral (IR and H-1 NMR) data. (C) 2008 Elsevier Masson SAS, All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.018
• 作为产物：
  描述：

  邻乙酰胺苯甲酸內酯 在 吡啶 、 hydrazine hydrate 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 3-(4- hydroxybenzylideneamino)-2-methylquinazolin-4(3H)-one
  参考文献：
  名称：

  Quinazolinone Platinum Metal Complexes: in silico Design, Synthesis and Evaluation of Anticancer Activity

  摘要：

  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。

  DOI：

  10.14233/ajchem.2018.21330

文献信息

• Synthesis, Characterization and Antioxidant Studies of Quinazolin Derivatives
  作者：Khalida Al-Azawi

  DOI：10.13005/ojc/320166

  日期：2016.3.25

  3-((4-(dimethylamino)benzylidene)amino)-2-methylquinazolin-4(3H)-one (3), 3-((4-hydroxybenzylidene)amino)-2-methylquinazolin-4(3H)-one (4), 2-methyl-3-(pyrrolidin-2-ylideneamino)quinazolin-4(3H)-one (5) and 3,3'-((1,4-phenylenebis(methanylylidene))bis(azanylylidene))bis(2-methylquinazolin-4(3H)-one) (6) derived from 3-amino-2-methylquinazolin-4(3H)-one have been synthesized and characterized by elemental analysis, FT-IR, NMR techniques and screened to establish their potential as antioxidants against 1,1-diphenyl-2-picrylhydrazyl (DPPH) and Nitric oxide (NO) radical scavengers. The results revealed that synthesized compounds (5 and 6) are much higher than common antioxidants ascorbic acid and they showed excellent scavenging capacity against DPPH and Nitric oxide (NO). The synthesized compounds (3 and 4) demonstrated encouraging results comparable with ascorbic acid.

  3-((4-(二甲氨基)苄叉氨基)-2-甲基喹唑啉-4(3H)-酮 (3)、3-((4-羟基苄叉氨基)-2-甲基喹唑啉-4(3H)-酮 (4)、2-甲基-3-(吡咯烷-2-叉氨基)喹唑啉-4(3H)-酮 (5) 和 3,3'-((1,4-苯ylene双(甲烷叉))双(氮烷叉))双(2-甲基喹唑啉-4(3H)-酮) (6) 来源于 3-氨基-2-甲基喹唑啉-4(3H)-酮，已被合成并通过元素分析、FT-IR、NMR 技术进行了表征，并进行了筛选以确定它们作为抗氧化剂对抗 1,1-二苯基-2-苦基肼 (DPPH) 和一氧化氮 (NO) 自由基清除剂的潜力。结果表明，合成的化合物 (5 和 6) 比常见抗氧化剂抗坏血酸高出许多，并且它们对 DPPH 和一氧化氮 (NO) 显示出出色的清除能力。合成的化合物 (3 和 4) 显示了与抗坏血酸相当令人鼓舞的结果。
• 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。
• Synthesis, antibacterial screening and computational studies of quinazoline-4 (3H)-one-triazole conjugates
  作者：Neha Manhas、Parvesh Singh、Ashona Singh-Pillay、Neil Koorbanally

  DOI：10.1016/j.molstruc.2023.136108

  日期：2023.11
• Synthesis and anti-inflammatory activity of newer quinazolin-4-one derivatives
  作者：Ashok Kumar、Chatrasal Singh Rajput

  DOI：10.1016/j.ejmech.2008.03.018

  日期：2009.1

  2-Methyl-3-aminosubstituted-3H-quinazolin-4-ones (1-2), 2-methyl-3-(substituted-arylidene-amino)-substituted-3H-quinazolin-4-ones (3-10), 2-bromomethyl-3-(substituted-arylidene-amino)-substituted-3H-quinazolin-4-ones (11-18), 2-(5'-pyridin-4-yl-[1,3,4]-oxadiazol-2-yl-sulfanylmethyl)-3-(substituted-arylidene-amino)-substituted-3H-quinazolin-4-ones (19-26), 3-(3-chloro-2-oxo-4-substituted-aryl-azetidin-1-yl)-2-(5-pyridin-4-yl-[1,3,4]-oxadiazol-2-yl-sulfanylmethyl)-substituted-3H-quinazolin-4-ones (27-34) and 3-(4-oxo-2-substituted-aryl-thiazolidin-3-yl)-2-(5-pyridin-4-yl-[1,3,4]-oxadiazol-2-yl-sulfanylmethyl)-substituted-3H-quinazolin-4-ones (35-42) were synthesized in present study. All the compounds exhibited anti-inflammatory activity at the dose 50 mg/kg p.o. varying degree from 16.3 to 36.3% inhibition of oedema. Compound 40 showed same activity at 25, 50 and 100 mg/kg p.o. like standard drugs. The structure of all these newly synthesized compounds was confirmed by their analytical (C, H, N) and spectral (IR and H-1 NMR) data. (C) 2008 Elsevier Masson SAS, All rights reserved.
• Cytotoxicity and Antibacterial Evaluation of <i>O</i> ‐Alkylated/Acylated Quinazolin‐4‐one Schiff Bases
  作者：Neha Manhas、Parvesh Singh、Chunderika Mocktar、Moganavelli Singh、Neil Koorbanally

  DOI：10.1002/cbdv.202100096

  日期：2021.5

  (SAR) analysis revealed that O‐alkylation generally increased the anticancer activity and selectivity of quinazoline‐4‐one Schiff bases toward Caco‐2 cells. The fluorinated Schiff‐base generally exhibited even more significant cytotoxic activity compared to their chlorine analogs. Surprisingly, none of the quinazoline‐4‐one Schiff bases displayed encouraging antibacterial activity against the bacterial

  合成了一系列喹唑啉-4-one Schiff 碱，并在体外测试了它们对两种癌细胞系（MCF-7、Caco-2）和一种人胚胎细胞系（HEK-293）的细胞毒性，包括它们对两种癌细胞的抗菌评估。革兰氏阳性和四种革兰氏阴性细菌菌株。大多数喹唑啉-希夫碱对 Caco-2 表现出有效的细胞毒性。3 - [（Ž） - （4 - [（丁-2-炔-1-基）氧基]苯基}亚甲基）氨基] -2-甲基喹唑啉-4（3 H ^） -酮（1207）与所述ø -丁炔官能团显示了三个倍高细胞毒性活性（IC 50相比，5-氟尿嘧啶（5-FU = 376.8μM）; IC 50=1086.1 微米）。然而，所有化合物都被发现对 HEK-293 有毒，除了 3-[( Z )-(4-[(2,4-二氟苯基)甲氧基]苯基}亚甲基)氨基]-2-甲基喹唑啉-4( 3 H )-one ( 6h ) 显示出比 5-FU 低约三倍的毒性和更高的选择性指数。构效关系