2-(furan-2-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one | 1542097-58-4

• 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: 2-(furan-2-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(Furan-2-yl)-3-phenyl-1,2-dihydroquinazolin-4-one；2-(furan-2-yl)-3-phenyl-1,2-dihydroquinazolin-4-one
• CAS: 1542097-58-4
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: KKRMYDSSQDBBFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硝基-N-苯基苯甲酰胺 在 palladium 10% on activated carbon 、 甲酸铵 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(furan-2-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Structural optimization of a retrograde trafficking inhibitor that protects cells from infections by human polyoma- and papillomaviruses

  摘要：

  Human polyoma- and papillomaviruses are non-enveloped DNA viruses that cause severe pathologies and mortalities. Under circumstances of immunosuppression, JC polyomavirus causes a fatal demyelinating disease called progressive multifocal leukoencephalopathy (PML) and the BK polyomavirus is the etiological agent of polyomavirus-induced nephropathy and hemorrhagic cystitis. Human papillomavirus type 16, another non-enveloped DNA virus, is associated with the development of cancers in tissues like the uterine cervix and oropharynx. Currently, there are no approved drugs or vaccines to treat or prevent polyomavirus infections. We recently discovered that the small molecule Retro-2(cycl), an inhibitor of host retrograde trafficking, blocked infection by several human and monkey polyomaviruses. Here, we report diversity-oriented syntheses of Retro-2(cycl) and evaluation of the resulting analogs using an assay of human cell infections by JC polyomavirus. We defined structure-activity relationships and also discovered analogs with significantly improved potency as suppressors of human polyoma- and papillomavirus infection in vitro. Our findings represent an advance in the development of drug candidates that can broadly protect humans from non-enveloped DNA viruses and toxins that exploit retrograde trafficking as a means for cell entry.

  DOI：

  10.1016/j.bmc.2014.06.053

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFECTIONS<br/>[FR] COMPOSÉS DESTINÉS AU TRAITEMENT ET À LA PRÉVENTION D'INFECTIONS
  申请人：UNIV BROWN

  公开号：WO2014014814A1

  公开（公告）日：2014-01-23

  Provided herein are compounds of Formula (I) or (II): (I) (II) harmaceutically acceptable salts, tautomers, prodrugs, and stereoisomers thereof, and pharmaceutical compositions thereof, wherein X, RN, R1,R3,R4, p, and m are as defined herein. Such compounds and compositions have been found useful in the treatment or prevention of viral infections, e.g., polyomaviral infections, and are further envisioned useful in treatment or prevention of other pathogenic conditions associated with endosomal trafficking. Methods of treating or preventing an infection by a pathogen secreting an AB5 toxin is also contemplated.

  本文提供了化合物的公式(I)或(II)：(I) (II) 其药用可接受的盐、互变异构体、前药和立体异构体，以及药物组合物，其中X、RN、R1、R3、R4、p和m如本文所定义。已发现这些化合物和组合物在治疗或预防病毒感染，例如聚病毒感染方面具有用处，并且进一步被认为在治疗或预防与溶酶体运输相关的其他病原体条件方面有用。还考虑了通过治疗或预防分泌AB5毒素的病原体感染的方法。
• CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
  作者：Jin Zhang、Decheng Ren、Yangmin Ma、Weitao Wang、Hao Wu

  DOI：10.1016/j.tet.2014.05.059

  日期：2014.8

  A CuO nanoparticle-catalyzed one-pot process has engineered for the preparation of diverse quinazolinones from the readily available isatoic anhydride, aldehydes and amine or ammonium. For amine substrates the reactions afford 2,3-dihydroquinazolin-4(1H)-ones in aqueous ethanol promoted by ultrasound irradiation. However, the ammonium substrates undergo intramolecular electron transfer and rearrangement

  一种由CuO纳米颗粒催化的一锅法，经设计可从容易获得的等角酸酐，醛和胺或铵制备各种喹唑啉酮。对于胺底物，反应得到在乙醇水溶液中由超声辐射促进的2，3-二氢喹唑啉-4（1 H）-one。然而，铵底物经历分子内电子转移和重排产生喹唑啉-4（3 H）一。该催化剂可循环使用四次而不会损失任何实质活性。其他显着特征还包括广泛的官能团耐受性（合成了46种喹唑啉酮，首先报道了其中的9种），并在温和条件下提供了中等至优异的收率。
• Para-Aminobenzoic acid grafted on silica-coated magnetic nanoparticles: a highly efficient and synergistic organocatalyst for on-water synthesis of 2,3-dihydroquinazolin-4(1H)-ones
  作者：Hamidreza FaniMoghadam、Mohammad G. Dekamin、Negin Rostami

  DOI：10.1007/s11164-022-04736-3

  日期：2022.7

  nanocomposite was used as a novel, highly efficient and synergistic recoverable organocatalyst for the synthesis of biologically active 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-one derivatives via on-water and one-pot three-component condensation of isatoic anhydride, aromatic aldehydes and aromatic or aliphatic amines under reflux conditions. Transition metal-free process, the use of a naturally

  在本研究中，制备了新的对氨基苯甲酸（PABA）接枝在二氧化硅包覆的磁性纳米粒子（Fe 3 O 4 @SiO 2 @Pr-PABA）上，并使用傅里叶变换红外（FT-IR）正确确认了其结构。 ) 光谱学、粉末 X 射线衍射 (XRD)、振动样品磁力计 (VSM)、场发射扫描电子显微镜 (FESEM)、能量色散 X 射线探测器 (EDS)、透射电子显微镜 (TEM)、热重分析 (TGA) )、N 2吸附-解吸技术 (BET) 和原子力显微镜 (AFM)。Fe 3 O 4 @SiO 2@Pr-PABA 纳米复合材料被用作一种新型、高效和协同的可回收有机催化剂，用于通过水和单-水合成具有生物活性的 2,3-二取代-2,3-二氢喹唑啉-4(1 H )-one 衍生物回流条件下，靛红酸酐、芳香醛和芳香胺或脂肪胺的锅三组分缩合反应。无过渡金属工艺、使用天然存在的组分和催化剂以及溶剂的环保性能、成本效益、催
• COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFECTIONS
  申请人：Brown University

  公开号：US20150166517A1

  公开（公告）日：2015-06-18

  Provided herein are compounds of Formula (I) or (II): (I) (II) pharmaceutically acceptable salts, tautomers, prodrugs, and stereoisomers thereof, and pharmaceutical compositions thereof, wherein X, R N , R 1 , R 3 , R 4 , p, and m are as defined herein. Such compounds and compositions have been found useful in the treatment or prevention of viral infections, e.g., polyomaviral infections, and are further envisioned useful in treatment or prevention of other pathogenic conditions associated with endosomal trafficking. Methods of treating or preventing an infection by a pathogen secreting an AB 5 toxin is also contemplated.
• US9695156B2
  申请人：——

  公开号：US9695156B2

  公开（公告）日：2017-07-04