5-bromo-3′-(p-tolyl)-1′H-spiro[indoline-3,2′-quinazoline]-2,4′(3′H)-dione | 933852-18-7

• 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: 5-bromo-3′-(p-tolyl)-1′H-spiro[indoline-3,2′-quinazoline]-2,4′(3′H)-dione
• 英文别名: 5-bromo-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione；5-Bromo-3'-p-tolyl-1'h-spiro[indoline-3,2'-quinazoline]-2,4'(3'h)-dione；5-bromo-3'-(4-methylphenyl)spiro[1H-indole-3,2'-1H-quinazoline]-2,4'-dione
• CAS: 933852-18-7
• 化学式: C₂₂H₁₆BrN₃O₂
• 分子量: 434.292
• InChiKey: XXURWWKBTCERQH-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  694.6±55.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴靛红 、 2-氨基-N-对甲苯苯甲酰胺 在 aluminum potassium sulfate dodecahydrate 作用下， 以 乙醇 为溶剂， 生成 5-bromo-3′-(p-tolyl)-1′H-spiro[indoline-3,2′-quinazoline]-2,4′(3′H)-dione
  参考文献：
  名称：

  一种高效且方便的合成新型1'H-螺[异吲哚啉-1,2，-喹唑啉] -3,4'（3'H）-二酮衍生物的方案

  摘要：

  摘要新型螺[异二氢吲哚-1,2'-喹唑啉]的合成中的有效和直接的过程-3,4-'（3' ħ） -二酮衍生物进行说明。该方法在回流下在乙醇中催化量的KAl（SO 4）2 .12H 2 O（alum）存在下，使用2-氨基苯甲酰胺和靛红的缩合反应。 图形概要

  DOI：

  10.1007/s00706-008-0040-3

文献信息

• A regioselective three-component reaction for synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives
  作者：Ali A. Mohammadi、M. Dabiri、H. Qaraat

  DOI：10.1016/j.tet.2009.02.037

  日期：2009.5

  regioselective three-component reaction of isatoic anhydride, isatins, and aromatic or aliphatic primary amines in the presence of catalytic amount of KAl(SO4)2·12H2O (alum) to yield a novel series of 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione is described.

  开环和靛红酸酐，靛红，和芳族或脂族伯胺的区域选择性三组分反应在KAL的催化量（SO存在4）2 ·12H 2 O（明矾），得到一个新的系列的第1' ħ -螺[异二氢吲哚-1,2'-喹唑啉] -3,4-'（3' ħ） -二酮进行说明。
• V‐N‐C catalysts anchored to mesoporous Al‐SBA‐15 with tailorable pore sizes for the synthesis of spirooxindole dihydroquinazolinones derivatives
  作者：Javad Safaei‐Ghomi、Raheleh Teymuri

  DOI：10.1002/aoc.5150

  日期：2019.10

  catalyst was successfully synthesized via anchoring of V‐bis(2‐aminobenzamide) complex on the Al‐SBA‐15. This modified mesoporous was identified by several characterization techniques, such as X‐ray diffraction, field emission‐scanning electron microscopy, Fourier transform‐infrared, Brunauer–Emmett–Teller and transmission electron microscopy. V‐Bis(2‐aminobenzamide)@Al‐SBA‐15 was found to be an efficient

  通过将V-双（2-氨基苯甲酰胺）配合物固定在Al-SBA-15上，成功地合成了多相纳米级催化剂。这种改性的介孔是通过几种表征技术鉴定的，例如X射线衍射，场发射扫描电子显微镜，傅里叶变换红外光谱，Brunauer-Emmett-Teller和透射电子显微镜。发现V-Bis（2-氨基苯甲酰胺）@ Al-SBA-15是一种有效的多相催化剂，可快速理想地合成各种螺环吲哚二氢喹唑啉酮衍生物。另外，该多相纳米催化剂在有机和水溶液中化学稳定，并且可以迅速重复使用至少七个循环，而不会显着降低催化活性。
• Convenient synthesis and evaluation of antioxidant property of functionalized spiro indolinone-dihydroquinazolinones
  作者：Tania Kundu、Animesh Pramanik

  DOI：10.1016/j.bioorg.2022.105830

  日期：2022.7

  In the present study an efficient synthetic pathway has been developed for the library synthesis of diversely functionalized spiro indolinone-dihydroquinazolinones from easily available isatins and 2-aminobenzamides by acid catalyzed condensation at 70 °C in ethanol. The outcome of the ROS scavenging analysis over the synthesized spiro compounds displays significant variation in their respective antioxidant

  在本研究中，已经开发了一种有效的合成途径，用于在 70°C 的乙醇中通过酸催化缩合从容易获得的靛红和 2-氨基苯甲酰胺中合成多种功能化的螺吲哚啉酮-二氢喹唑啉酮。对合成的螺环化合物的 ROS 清除分析结果显示，它们各自的抗氧化性能随着不同位置取代基的变化而显着变化。值得注意的是，在吲哚啉酮或二氢喹唑啉酮部分的氮原子上被苯环取代的螺环化合物对OH（在 80 µM 时对对照约为 83%）和 O 2 -显示出有希望的防御能力（在 20 µM 时 ≈ 78% 对抗肾上腺素自动氧化）。几乎每一种螺环化合物都表现出显着的还原能力，特别是含有在酰胺氮（N-3）处被芳环取代的二氢喹唑啉酮部分的化合物表现出显着的还原性。IC 50和 TEAC（Trolox 等效抗氧化能力）值表明，苯环取代吲哚氮 (N-1) 的螺环化合物具有显着的抗氧化效力 (IC 50  ≈ 22.67 µM) 和相当大的OH 清除能力 (TEAC
• Microwave Heated Flow Synthesis of Spiro-oxindole Dihydroquinazolinone Based IRAP Inhibitors
  作者：Karin Engen、Jonas Sävmarker、Ulrika Rosenström、Johan Wannberg、Thomas Lundbäck、Annika Jenmalm-Jensen、Mats Larhed

  DOI：10.1021/op500237k

  日期：2014.11.21

  A fast and convenient synthetic route towards spiro-oxindole dihydroquinazolinones as novel and drug-like insulin-regulated aminopeptidase (IRAP) inhibitors is reported. The synthesis is performed using a MW heated continuous flow system employing 200 mm X 3 mm i MW absorbing silicon carbide (SiC) or MW transparent borosilicate tubular reactors. A three-component MW-flow reaction to build up the spiro compounds (9 examples, 4087% yield), using the SiC reactor, as well as a SuzukiMiyaura cross-coupling reaction (71%), employing the borosilicate reactor, are presented with residence times down to 168 s. The continuous MW-flow routes provide a smooth and scalable synthetic methodology towards this class of IRAP inhibitors.
• Design, synthesis and docking studies of some spiro-oxindole dihydroquinazolinones as antibacterial agents
  作者：Jin Zhang、Jiawen Zhao、Liangpeng Wang、Jia Liu、Decheng Ren、Yangmin Ma

  DOI：10.1016/j.tet.2015.12.055

  日期：2016.2

  Two series of spiro-oxindole dihydroquinazolinone derivatives have been designed and synthesized using a catalytic amount of nano cerium oxide with excellent product yields by a convenient one-pot process. The synthesized compounds were evaluated for their in vitro antibacterial activity, and compounds 1i-1p showed considerable antibacterial activities to Escherichia coli. Molecular docking of E. coli Biotin Carboxylase (EcBC) enzyme was also performed in order to predict the interactions of the synthesized compounds. (C) 2016 Published by Elsevier Ltd.