4-(4-氧代喹唑啉)苯甲酸 | 94242-54-3

• 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-氧代喹唑啉)苯甲酸
• 英文名称: 3-(4-carboxylphenyl)-4(3H)-quinazolinone
• 英文别名: 3-(4-carboxylphenyl)quinazolin-4(3H)-one；4-(4-oxoquinazolin-3(4H)-yl)benzoic acid；3-(4-carboxyphenyl)quinazolin-4(3H)-one；4-(Chinazolin-4-on-3-yl)-benzoesaeure；4-(4-oxo-4H-quinazolin-3-yl)-benzoic acid；4-(4-Oxo-4H-chinazolin-3-yl)-benzoesaeure；4-(4-oxoquinazolin-3-yl)benzoic acid
• CAS: 94242-54-3
• 化学式: C₁₅H₁₀N₂O₃
• mdl: MFCD03473182
• 分子量: 266.256
• InChiKey: GTGLPZFNBPATOL-UHFFFAOYSA-N

物化性质

• 熔点：
  240-242 °C(Solv: ethanol (64-17-5))
• 沸点：
  519.7±52.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (R)-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine 、 4-(4-氧代喹唑啉)苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-4-(4-oxoquinazolin-3(4H)-yl)-N-(6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide
  参考文献：
  名称：

  Discovery of Potent, Orally Bioavailable Phthalazinone Bradykinin B1 Receptor Antagonists

  摘要：

  The bradykinin B1 receptor is rapidly induced upon tissue injury and inflammation, stimulating the production of inflammatory mediators resulting in plasma extravasation, leukocyte trafficking, edema, and pain. We have previously reported on sulfonamide and sulfone-based B1 antagonists containing a privileged bicyclic amine moiety leading to potent series of 2-oxopiperazines. The suboptimal pharmacokinetics and physicochemical properties of the oxopiperazine sulfonamides led us to seek B1 antagonists with improved druglike properties. Using a pharmacophore model containing a bicyclic amine as anchor, we designed a series of amide antagonists with targeted physicochemical properties. This approach led to a novel series of potent phthalazinone B1 antagonists, where we successfully replaced a sulfonamide acceptor with a cyclic carbonyl unit. SAR studies revealed compounds with subnanomolar B1 binding affinity. These compounds demonstrate excellent cross-species PK properties with high oral bioavailability and potent activity in a rabbit biochemical challenge pharmacodynamic study.

  DOI：

  10.1021/jm200808v
• 作为产物：
  描述：

  N-(2-nitrobenzyl)-4-methylaniline 在 盐酸 、 tin 、 potassium permanganate 作用下， 生成 4-(4-氧代喹唑啉)苯甲酸
  参考文献：
  名称：

  Paal; Busch, Chemische Berichte, 1889, vol. 22, p. 2693

  摘要：

  DOI：

文献信息

• Furan-2-carbaldehydes as C1 building blocks for the synthesis of quinazolin-4(3<i>H</i>)-ones <i>via</i> ligand-free photocatalytic C–C bond cleavage
  作者：Wenjia Yu、Xianwei Zhang、Bingjie Qin、Qiyang Wang、Xuhong Ren、Xinhua He

  DOI：10.1039/c8gc00079d

  日期：——

  efficient green C1 building blocks to synthesize bioactive quinazolin-4(3H)-ones by ligand-free photocatalytic C–C bond cleavage. Notably, protection of hydroxyl, carboxyl, amide, or secondary amino groups is not required. Mechanistic studies suggest that conjugated N,O-tridentate copper complexes act as novel photoinitiators under visible light.

  呋喃-2-甲醛作为生物质衍生的化学品，被用作有效的绿色C1构建基块，可通过无配体的光催化C–C键裂解来合成生物活性喹唑啉4（3 H）-酮。特别地，不需要保护羟基，羧基，酰胺或仲氨基。机理研究表明，在可见光下，共轭的N，O-三齿铜络合物可作为新型光引发剂。
• Efficient Iodine-catalyzed Synthesis of 3-Aryl 4(3<i>H</i>)-quinazolinones
  作者：Min Wang、Zhi-Guo Song、Ting-Ting Zhang

  DOI：10.1080/00304941003697669

  日期：2010.4.8

  There are several methods for the preparation of this class of compounds. The most direct procedure includes the condensation of anthranilic acid, ortho esters and amines in the presence of various catalysts such as NaHSO4 or Amberlyst-15,9 Yb(III)-resin,10 Yb(OTf)3, Bi(TFA)3-[nbp]FeCl4 ionic liquid,12 La(NO3)3·6H2O or p-toluenesulfonic acid,13 Keggin-type heteropolyacid,14 SnCl4·4H2O, and SiO2-FeCl3

  具有 4-喹唑啉酮基序的化合物显示出多种有趣的药理学特性，例如抗疟、抗肿瘤、抗惊厥、抗炎、杀真菌、抗菌和溶钙活性。 1-7 文献检查表明 4-喹唑啉酮取代了 3-由于它们似乎具有重要的镇静、催眠和抗惊厥作用，因此这一位置引起了化学家的注意。8 有几种制备此类化合物的方法。最直接的方法包括在各种催化剂（如 NaHSO4 或 Amberlyst-15,9 Yb(III)-树脂、10 Yb(OTf)3、Bi(TFA)3-）存在下，邻氨基苯甲酸、原酸酯和胺的缩合反应。 [nbp]FeCl4离子液体、12 La(NO3)3·6H2O或对甲苯磺酸、13 Keggin型杂多酸、14 SnCl4·4H2O、SiO2-FeCl3。虽然这种类型的多组分反应 (MCR) 可以在一个步骤中生产所需的产品，但其中一些方法具有某些缺点，例如昂贵的催化剂、高温 (60–80°C)、反应时间长 (20 h) ，以及使用有
• SnCl₂· 2H₂O-catalyzed one-pot synthesis of 4(3<i>H</i>)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions
  作者：Min Wang、Zhiguo Song、Tingting Zhang

  DOI：10.1002/jhet.330

  日期：——

  A simple, efficient, and green procedure for the one‐pot synthesis of 4(3H)‐quinazolinones by three components condensation of anthranilic acid, ortho esters, and amines in the presence of SnCl2 · 2H2O has been developed. The reaction occurred within short reaction time at room temperature under solvent‐free conditions to afford the title products in excellent yields. J. Heterocyclic Chem., (2010)

  已经开发了一种简单，高效且绿色的方法，可在SnCl 2 ·2H 2 O存在下通过邻氨基苯甲酸，原酸酯和胺的三组分缩合一锅合成4（3 H）-喹唑啉酮。该反应在无溶剂条件下于室温下在较短的反应时间内发生，从而以优异的收率得到标题产物。J.杂环化​​学。（2010）。
• Ammonium Chloride–Catalyzed One-Pot Synthesis of 4(3<i>H</i>)-Quinazolinones Under Solvent-Free Conditions
  作者：Guoli Huang、Bo Liu、Mingyu Teng、Yegao Chen

  DOI：10.1080/00397911.2013.873467

  日期：2014.6.18

  Ammonium chloride, which is a very inexpensive and readily available reagent, can efficiently catalyze three-component, one-pot condensation reactions of 2-amino-benzoic acid esters, ortho esters, and aromatic amines to afford the corresponding 4(3H)-quinazolinones in good to excellent yields under solvent-free conditions.
• Suesse, M.; Johne, S., Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 6, p. 1027 - 1033
  作者：Suesse, M.、Johne, S.

  DOI：——

  日期：——