3-{[(4-hydroxy-3-methoxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one | 106873-10-3

• 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-hydroxy-3-methoxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one
• 英文别名: 2-phenyl-3-amino-4(3H)-quinazolone-vanillin；3-[(4-Hydroxy-3-methoxyphenyl)methylideneamino]-2-phenylquinazolin-4-one
• CAS: 106873-10-3
• 化学式: C₂₂H₁₇N₃O₃
• 分子量: 371.395
• InChiKey: AVTAJBSUYLXBTK-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  584.9±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氯化铬 、 3-{[(4-hydroxy-3-methoxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one 在 sodium acetate 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Kumar; Sharma, Journal of the Indian Chemical Society, 1991, vol. 68, # 10, p. 539 - 541

  摘要：

  DOI：
• 作为产物：
  描述：

  苯草灭 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-{[(4-hydroxy-3-methoxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis, spectroscopic characterization, antineoplastic, in vitro-cytotoxic, and antibacterial activities of mononuclear ruthenium(II) complexes

  摘要：

  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.

  DOI：

  10.1080/00958972.2012.663082

文献信息

• 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。
• 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：——