3-phenyl-2-(thiophen-2-yl)-2,3-dihydroquinazolin-4(1H)-one | 361984-43-2

• 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-phenyl-2-(thiophen-2-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 3-phenyl-2-thiophen-2-yl-1,2-dihydroquinazolin-4-one
• CAS: 361984-43-2
• 化学式: C₁₈H₁₄N₂OS
• 分子量: 306.388
• InChiKey: KCHBRRCLUGULSC-UHFFFAOYSA-N

物化性质

• 熔点：
  197-200 °C(Solv: ethanol (64-17-5))
• 沸点：
  524.3±50.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  60.6
• 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 3-phenyl-2-(thiophen-2-yl)-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

• Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
  作者：Yang Yang、Renzhong Fu、Yang Liu、Jing Cai、Xiaojun Zeng

  DOI：10.1016/j.tet.2020.131312

  日期：2020.7

  3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational

  在微波促进下，通过杂多阴离子基离子液体催化的等位酸酐，胺和醛（或酮）通过一锅三组分反应合成了一系列2,3-二氢喹唑啉-4（1 H）-one衍生物。条件。发现该实用方案可耐受具有不同官能团的多种底物。中等至极好的产量，无溶剂介质和操作简便是主要亮点。此外，催化剂可以回收和再利用而没有明显的反应性损失。与现有方法相比，该方法提供了绿色且经过改进的协议。
• [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。
• Synthesis of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones using CoAl2O4 nanoparticles as heterogeneous catalyst
  作者：Fatemeh Ahmadian、Alireza Barmak、Esmali Ghaderi、Masoumeh Bavadi、Hossein Raanaei、Khodabakhsh Niknam

  DOI：10.1007/s13738-019-01729-9

  日期：2019.12

  AbstractThe preparation and characterization of cobalt aluminate (CoAl2O4) magnetic nanoparticles and its application as a catalyst for the synthesis of a novel class of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones is described. The structure of the catalyst was studied by Fourier transform infrared spectroscopy, transmission electron microscopy, X-ray diffraction, and vibrating sample

  摘要描述了铝酸钴（CoAl 2 O 4）磁性纳米颗粒的制备，表征及其在合成新型吡唑-喹唑啉酮和2,3-二氢喹唑啉-4（1H）-ones催化剂中的应用。通过傅里叶变换红外光谱，透射电子显微镜，X射线衍射和振动样品磁力计分析研究了催化剂的结构。所得的铝酸钴（CoAl 2 O 4）是有效的催化剂，并以良好至优异的产率提供了所需的产物。而且，该催化剂可以容易地通过磁分离回收并循环四次而不会显着损失其催化活性。 图形摘要以CoAl 2 O 4为纳米颗粒非均相催化剂，在乙醇回流条件下，通过等规酸酐，芳族醛和胺的一锅缩合反应，合成了2,3-二氢喹唑啉-4（1H）-和一类新型的吡唑-喹唑啉酮。
• Dihydroquinazolin-4(1H)-one derivatives as novel and potential leads for diabetic management
  作者：Oluwatoyin Babatunde、Shehryar Hameed、Uzma Salar、Sridevi Chigurupati、Abdul Wadood、Ashfaq Ur Rehman、Vijayan Venugopal、Khalid Mohammed Khan、Muhammad Taha、Shahnaz Perveen

  DOI：10.1007/s11030-021-10196-5

  日期：2022.4

  A variety of dihydroquinazolin-4(1H)-one derivatives (1–37) were synthesized via “one-pot” three-component reaction scheme by treating aniline and different aromatic aldehydes with isatoic anhydride in the presence of acetic acid. Chemical structures of compounds were deduced by different spectroscopic techniques including EI-MS, HREI-MS, 1H-, and 13C-NMR. Compounds were subjected to α-amylase and

  通过“一锅法”三组分反应方案，在乙酸存在下，用靛红酸酐处理苯胺和不同的芳香醛，合成了多种二氢喹唑啉-4(1 H )-酮衍生物 ( 1-37 )。化合物的化学结构通过不同的光谱技术推断，包括 EI-MS、HREI-MS、1 H-和13 C-NMR。化合物具有α-淀粉酶和α-葡糖苷酶抑制活性。许多衍生物对α -淀粉酶 (IC 50  = 23.33 ± 0.02—88.65 ± 0.23 μM) 和α -葡萄糖苷酶 (IC 50 = 25.01 ± 0.12—89.99 ± 0.09 μM) 酶，分别。将结果与标准阿卡波糖（α-淀粉酶的 IC 50 = 17.08 ± 0.07 μM 和 α - 葡萄糖苷酶的IC 50  = 17.67 ± 0.09 μM）进行比较。通过分析取代基对抑制潜力的影响，使构效关系（SAR）合理化。进行动力学研究以发现化合物的抑制模式，这些化合物揭示了对α-淀粉酶的
• 一种选择性合成多取代二氢喹唑啉酮或喹唑 啉酮的方法
  申请人：常熟理工学院

  公开号：CN110372611B

  公开（公告）日：2021-05-04

  本发明公开了一种选择性合成多取代二氢喹唑啉酮或喹唑啉酮的方法。本方法以杂多酸类离子液体为催化剂，利用微波加热和无溶剂合成技术，以靛红酸酐或其衍生物、胺和醛做原料的“一锅法”合成策略选择性合成二氢喹唑啉酮和喹唑啉酮衍生物。与现有技术相比，本发明具有高效率、低成本、绿色环保、反应选择性好、产物收率高、可选择性合成、催化剂回收套用方便、操作简单，便于工业化大规模生产等多个优点，是一种环境友好的高效选择性合成的新方法，符合绿色化学的发展理念。