3-(4-氧代-3,4-二氢-2-喹唑啉)-丙酸 | 5368-37-6

• 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-氧代-3,4-二氢-2-喹唑啉)-丙酸
• 英文名称: 3-(4-oxo-3,4-dihydroquinazolin-2-yl)propanoic acid
• 英文别名: 3-(4-Oxo-3,4-dihydroquinazolin-2-yl)propanoic acid；3-(4-oxo-3H-quinazolin-2-yl)propanoic acid
• CAS: 5368-37-6
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD03955531
• 分子量: 218.212
• InChiKey: HYSISEGNFBAVMJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  >32.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 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：

  3-(4-氧代-3,4-二氢-2-喹唑啉)-丙酸 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 反应 0.5h， 以71%的产率得到2,3-dihydropyrrolo[2,1-b]quinazoline-1,9-dione
  参考文献：
  名称：

  Reaction of anthranilic acid amides with cyclic anhydrides

  摘要：

  Anthranilic acid amide reacts with cyclic anhydrides to give the corresponding N-acyl derivatives at the amino group, while analogous reactions of o-aminobenzohydroxamic acid lead to fori-nation of 3-hydroxy-quinazolin-4-ones under mild conditions. N-Acyl derivatives of anthranilic acid amide undergo intramolecular cyclization to imides on microwave irradiation or on melting, and their treatment with acetic anhydride in the presence of sodium acetate on heating yields quinazolin-4-ones.

  DOI：

  10.1134/s1070428006030079
• 作为产物：
  描述：

  2-氨基苯甲腈 在 过氧化脲素 、 potassium carbonate 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 生成 3-(4-氧代-3,4-二氢-2-喹唑啉)-丙酸
  参考文献：
  名称：

  Chemical Probes to Study ADP-Ribosylation: Synthesis and Biochemical Evaluation of Inhibitors of the Human ADP-Ribosyltransferase ARTD3/PARP3

  摘要：

  The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl]propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of SS compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.

  DOI：

  10.1021/jm401394u

文献信息

• Anti-inflammatory and Antioxidant Peptide-Conjugates: Modulation of Activity by Charged and Hydrophobic Residues
  作者：K. P. Rakesh、R. Suhas、D. Channe Gowda

  DOI：10.1007/s10989-017-9668-3

  日期：2019.3

  activities of a series of quinazolinone-conjugated-peptides were investigated. Substitution of second position of the peptide template ‘GXGVP’ by different amino acids of varying hydrophobicity, charge and polarity has been studied. Quinazolinone-peptides with Trp residue emerged out as the highly potential antioxidant whereas the conjugate with Asp moiety turned to be a good anti-inflammatory agent. These

  在本研究中，研究了一系列喹唑啉酮共轭肽的抗氧化和抗炎活性。已经研究了由疏水性，电荷和极性不同的不同氨基酸取代肽模板“ GXGVP”的第二位。具有Trp残基的喹唑啉酮肽作为高潜力的抗氧化剂出现，而具有Asp部分的缀合物成为一种良好的抗炎剂。这些数据表明，更多的疏水性有利于抗氧化性能，相反，分子中带电物质的存在有助于减轻炎症。此外，在杂环部分中具有丁基并且在肽部分中具有游离C末端的缀合物表现出良好的减轻炎症的特性。因此，疏水基团的变化
• Anticancer and DNA binding studies of potential amino acids based quinazolinone analogs: Synthesis, SAR and molecular docking
  作者：K.P. Rakesh、H.K. Kumara、H.M. Manukumar、D. Channe Gowda

  DOI：10.1016/j.bioorg.2019.03.038

  日期：2019.6

  A novel series of amino acids conjugated quinazolinone-Schiff’s bases were synthesized and screened for their in vitro anticancer activity and validated by molecular docking and DNA binding studies. In the present investigations, compounds 32, 33, 34, 41, 42 and 43 showed most potent anticancer activity against tested cancer cell lines and DNA binding study using methyl green comparing to doxorubicin

  合成了一系列新颖的氨基酸缀合的喹唑啉酮-席夫氏碱，并对其体外抗癌活性进行了筛选，并通过分子对接和DNA结合研究进行了验证。在本研究中，化合物32、33、34、41、42和43对被测试的癌细胞系显示出最有效的抗癌活性，并且使用甲基绿的DNA结合研究分别将阿霉素和溴化乙锭作为阳性对照。结构-活性关系（SAR）表明，色氨酸和苯丙氨酸衍生的给电子基团（OH和OCH 3）有利于DNA结合研究和抗癌活性。吸电子基团（Cl，NO 2和F）显示出最小的抗癌活性。分子对接研究中，结合最活跃的化合物的相互作用33，34，42和43通过表面结合相互作用堆叠有A-T丰富DNA小沟的区域被证实了。
• Amino acids conjugated quinazolinone-Schiff’s bases as potential antimicrobial agents: Synthesis, SAR and molecular docking studies
  作者：K.P. Rakesh、H.K. Kumara、B.J. Ullas、J. Shivakumara、D. Channe Gowda

  DOI：10.1016/j.bioorg.2019.103093

  日期：2019.9

  interaction, molecular docking was performed on active site ofglucosamine-6-Phosphate (GlcN-6-P) synthase (PDB ID: 2VF5) which showed good binding profile. Molecular docking studies and Preliminary structure-activity (SAR) relationship revealed that the tryptophan and phenylalanine conjugated quinazolinones with electron donating groups (OH and OCH3) were found to be excellent antimicrobial activities

  合成了一系列氨基酸缀合的喹唑啉酮-席夫氏碱，并通过分析和光谱法对其进行了表征。筛选所有合成的类似物（8-43）和中间体（1-7）的体外抗菌和抗真菌活性。在抗菌活性方面，化合物12-16、21-25、30-34和39-43表现出优异的抗菌活性，优于抗菌标准链霉素。化合物15、23-25、30-34、36和38-43表现出优异的抗真菌活性，比参考抗真菌药物Bavistin更具活性。此外，为了理解生物学活性与药物-受体相互作用的相关性，对葡糖胺-6-磷酸（GlcN-6-P）合酶（PDB ID：2VF5）的活性位点进行了分子对接，其表现出良好的结合特性。分子对接研究和初步结构活性（SAR）关系表明，色氨酸和苯丙氨酸共轭的带电子给体（OH和OCH3）的喹唑啉酮具有出色的抗菌活性，优于甘氨酸和丙氨酸共轭的衍生物。这可以通过氨基酸的芳香性和疏水性的贡献来解释。在该系列中，化合物41和43对抗菌活性显示出
• Effect of Low Charge and High Hydrophobicity on Antimicrobial Activity of the Quinazolinone-Peptide Conjugates
  作者：Kadallipura Puttaswamy Rakesh、Suhas Ramesh、Shivakumar、Dase Channe Gowda

  DOI：10.1134/s1068162018020036

  日期：2018.3

  against Gram-positive and Gram-negative bacteria. In particular, Trp, Tyr, and Phe-containing peptides showed greater antimicrobial potency than the reference standards. Alkyl chain length variations in heterocyclic moiety indicated that hybrids with propyl group were more active than butyl derivatives. Improved results were observed for debenzylated versions of the conjugates compared to their benzylated

  设计了相对低电荷和大量疏水性氨基酸的肽。设计肽的氨基酸序列为 GXGVP，其中 X 等于 W、Y、F、D 和 T，具有疏水、带电和极性单元的组合。这些肽与喹唑啉酮连接，以获得具有协同特性的一类新化合物。这些杂种对革兰氏阳性菌和革兰氏阴性菌显示出抗菌活性。特别是，含有 Trp、Tyr 和 Phe 的肽显示出比参考标准更高的抗菌效力。杂环部分中烷基链长的变化表明具有丙基的杂化物比丁基衍生物更具活性。与它们的苄基化对应物相比，观察到脱苄基形式的缀合物的改进结果。
• 3-Propynyl-2-substituted Carboxylic Acid Derivatives of Quinazolinone
  作者：C. O. USIFOH

  DOI：10.3797/scipharm.aut-00-25

  日期：——

  Alkylation of quinazolinone-2-carboxylic acids with propargyl bromide in dimethylformamide in the presence of potassium carbonate afforded 3-prop-2-ynyl quinazolinone-2-substituted carboxylic acid derivatives. Further reaction of 4b-c produced 5b-c, which indicates that N-alkylation occurs before esterification with a propynyl moiety.

  喷甲基溴代炔基喹噁唑酮-2-羧酸在二甲基甲酰胺中与碳酸钾反应，得到3-丙-2-炔基喹噁唑酮-2-取代羧酸衍生物。4b-c的进一步反应产生了5b-c，这表明N-烷基化发生在与丙炔基团酯化之前。