1-(3-fluorobenzyl)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione | 57384-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1-(3-fluorobenzyl)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
• 英文别名: 1-(m-Fluorbenzyl)-2H-3,1-benzoxazin-2,4(1H)-dion；1-(3-fluoro-benzyl)-1H-benzo[d][1,3]oxazine-2,4-dione；1-[(3-Fluorophenyl)methyl]-3,1-benzoxazine-2,4-dione
• CAS: 57384-89-1
• 化学式: C₁₅H₁₀FNO₃
• 分子量: 271.248
• InChiKey: SFTIPFRZROWMMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-fluorobenzyl)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 在 盐酸羟胺 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 1-(3-fluorobenzyl)-3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and antibiofilm evaluation of 3-hydroxy-2,3-dihydroquinazolin-4(1H)-one derivatives against opportunistic pathogen Acinetobacter baumannii

  摘要：

  The emergence of multidrug resistant microorganisms has triggered the impending need for new aitimicrobial strategies. The antivirulence strategy with the benefite of alleviating the drug resistance becomes the focus of research. In this study, 22 quorum sensing inhibitors were synthesized by mimicking the structure of autoinducer and acinetobactin and up to 34% biofilm inhibition was observed with 5u. The biofilm inhibition effect was further demonstrated with extracellular polysaccharides inhibition and synergism with Gentamycin sulphate.

  DOI：

  10.1016/j.bmc.2020.115606
• 作为产物：
  描述：

  靛红酸酐 、 3-氟溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以71%的产率得到1-(3-fluorobenzyl)-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
  参考文献：
  名称：

  N1-官能化喹唑啉-2,4-二酮的 (Isoxazolidin-3-yl) 膦酸酯缀合物的设计、合成、抗水痘带状疱疹和抗菌活性

  摘要：

  N-取代的C- (二乙氧基膦酰基)硝酮与N 3 -烯丙基-N 1 -苄基喹唑啉-2,4-二酮的偶极环加成产生非对映异构体3-(二乙氧基膦酰基)异恶唑烷与N 1 -苄基喹唑啉-2,4-的混合物C5 处的二酮单元。评估获得的化合物的抗病毒和抗菌活性。几种化合物对 VZV 显示出中等抑制活性，EC 50值在 12.63–58.48 µM 范围内。异恶唑烷顺式- 20c /反式- 20c (6:94) 的混合物被发现对蜡状芽孢杆菌最有效PCM 1948，MIC 值为 0.625 mg/mL，在该浓度下也没有致突变性。

  DOI：

  10.3390/molecules27196526

文献信息

• The chemistry of 2<i>H</i>-3,1-benzoxazine-2,4(1<i>H</i>)dione (isatoic anhydrides) 1. The synthesis of<i>N</i>-substituted 2<i>H</i>-3,1-benzoxazine-2,4(1<i>H</i>)diones
  作者：Goetz E. Hardtmann、Gabor Koletar、Oskar R. Pfister

  DOI：10.1002/jhet.5570120325

  日期：1975.6

  Three methods for the preparation of N-substituted 2H-3,1-benzoxazine-2,4(1H)diones (isatoic anhydrides) (1) utilizing 2-chloro-, 2-nitrobenzoic acids and N-unsubstituted isatoic anhydrides as starting materials, are described.

  三种制备N-取代的2 H -3,1-苯并恶嗪-2,4（1 H）二酮（乙酸酐）的方法（1）使用2-氯-，2-硝基苯甲酸和N-未取代的等角酸酐作为制备方法描述了起始材料。
• THE CHEMISTRY OF 2H-3,1-BENZOXAZINE-2,4(1H)-DIONE (ISATOIC ANHYDRIDE). XXIV.<i>N</i>-BENZYLATION OF ISATOIC ANHYDRIDE UNDER MITSUNOBU CONDITIONS
  作者：Gary M. Coppola

  DOI：10.1081/scc-120003148

  日期：2002.1

  ABSTRACT Isatoic anhydride is readily alkylated on nitrogen with benzylic alcohols in the presence of triphenylphosphine and diethyl azodicarboxylate. Both electron donating and electron withdrawing groups are tolerated.

  摘要 在三苯基膦和偶氮二甲酸二乙酯的存在下，靛红酸酐很容易用苄醇在氮上烷基化。供电子基团和吸电子基团都是可以容忍的。
• HARDTMANN G. E.; KOLETAR G.; PFISTER O. R.; GOGERTY J. H.; IORIO L. C., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 5, 447-453
  作者：HARDTMANN G. E.、 KOLETAR G.、 PFISTER O. R.、 GOGERTY J. H.、 IORIO L. C.

  DOI：——

  日期：——
• Synthesis and antibiofilm evaluation of 3-hydroxy-2,3-dihydroquinazolin-4(1H)-one derivatives against opportunistic pathogen Acinetobacter baumannii
  作者：Guo Yang、Cheng Cheng、Guo-Bo Xu、Lei Tang、Kim-Lee Chua、Yuan-Yong Yang

  DOI：10.1016/j.bmc.2020.115606

  日期：2020.8

  The emergence of multidrug resistant microorganisms has triggered the impending need for new aitimicrobial strategies. The antivirulence strategy with the benefite of alleviating the drug resistance becomes the focus of research. In this study, 22 quorum sensing inhibitors were synthesized by mimicking the structure of autoinducer and acinetobactin and up to 34% biofilm inhibition was observed with 5u. The biofilm inhibition effect was further demonstrated with extracellular polysaccharides inhibition and synergism with Gentamycin sulphate.
• Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
  作者：Magdalena Łysakowska、Iwona E. Głowacka、Graciela Andrei、Dominique Schols、Robert Snoeck、Paweł Lisiecki、Magdalena Szemraj、Dorota G. Piotrowska

  DOI：10.3390/molecules27196526

  日期：——

  diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N1-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities against VZV with EC50 values in the range of 12.63–58.48 µM. A mixture of isoxazolidines cis-20c/trans-20c (6:94) was found to be the most active against B. cereus PCM

  N-取代的C- (二乙氧基膦酰基)硝酮与N 3 -烯丙基-N 1 -苄基喹唑啉-2,4-二酮的偶极环加成产生非对映异构体3-(二乙氧基膦酰基)异恶唑烷与N 1 -苄基喹唑啉-2,4-的混合物C5 处的二酮单元。评估获得的化合物的抗病毒和抗菌活性。几种化合物对 VZV 显示出中等抑制活性，EC 50值在 12.63–58.48 µM 范围内。异恶唑烷顺式- 20c /反式- 20c (6:94) 的混合物被发现对蜡状芽孢杆菌最有效PCM 1948，MIC 值为 0.625 mg/mL，在该浓度下也没有致突变性。