3-[(furan-2-yl)methyl]quinazoline-2,4-dione | 436855-78-6

• 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-[(furan-2-yl)methyl]quinazoline-2,4-dione
• 英文别名: 3-furfurylquinazoline-2,4-dione；3-(2-furylmethyl)quinazoline-2,4(1H,3H)-dione；3-(furan-2-ylmethyl)quinazoline-2,4(1H,3H)-dione；3-(furan-2-ylmethyl)-1H-quinazoline-2,4-dione
• CAS: 436855-78-6
• 化学式: C₁₃H₁₀N₂O₃
• mdl: MFCD03982051
• 分子量: 242.234
• InChiKey: NZDDWKJGYHDQBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Dicyclohexyl 2-[[5-(hydroxymethyl)-2-methyl-2-bicyclo[2.2.1]heptanyl]methylamino]butanedioate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-[(furan-2-yl)methyl]quinazoline-2,4-dione
  参考文献：
  名称：

  [DE] VERFAHREN ZUR DURCHFÜHRUNG CHEMISCHER REAKTIONEN UNTER BETEILIGUNG VON AN FLUORIERTEN TRÄGERMATERIALIEN ÜBER FLUOR-FLUOR-WECHSELWIRKUNGEN ADSORBIERTEN VERBINDUNGEN
  [EN] METHOD FOR CARRYING OUT CHEMICAL REACTIONS INVOLVING COMPOUNDS ADSORBED ON FLUORINATED CARRIER MATERIALS BY MEANS OF FLUORINE-FLUORINE INTERACTIONS
  [FR] PROCEDE DE REALISATION DE REACTIONS CHIMIQUES EN PRESENCE DE COMPOSES ABSORBES SUR DES SUPPORTS FLUORES PAR INTERACTIONS FLUOR-FLUOR

  摘要：

  这项发明涉及一种在涉及化合物A-F的情况下通过化合物B进行化学反应的方法，其中化合物A-F通过氟-氟相互作用吸附在氟化载体材料FT上形成一个加合物(A-F):(FT)，其特征在于，将加合物(A-F):(FT)悬浮在含有化合物B的适当溶剂中，从而使得化合物B在参与吸附的化合物A-F的作用下与反应产物B'发生反应。

  公开号：

  WO2004013068A1

文献信息

• Multistep Parallel Synthesis of Quinazoline-2,4-diones by a Fluorous Biphasic Concept without Perfluorinated Solvents
  作者：Dominik Schwinn、Heiko Glatz、Willi Bannwarth

  DOI：10.1002/hlca.200390010

  日期：2003.1

  benzyl alcohol adsorbed via fluorous–fluorous interactions on fluorous reversed-phase silica gel (FRPSG), we have performed a multistep synthesis leading finally to a small library of quinazoline-2,4-diones. The whole reaction sequence runs without isolation of intermediates and most importantly, without the need of perfluorinated solvents.

  基于通过氟反相硅胶（FRPSG）上的氟-氟相互作用吸附的全氟标签苄醇，我们进行了多步合成，最终形成了一个小的喹唑啉-2,4-二酮文库。整个反应过程无需分离中间体，最重要的是，不需要全氟化溶剂。
• Traceless synthesis of quinazoline-2,4-diones by curtius rearrangement reaction using poly(ethylene glycol) as soluble polymeric support
  作者：Yanling Huang、Cuifen Lu、Zuxing Chen、Guichun Yang

  DOI：10.1002/jhet.5570440628

  日期：2007.11

  We have developed an efficient method to synthesize various quinazoline-2,4-diones using poly-(ethylene glycol) as soluble polymeric support. The procedure of this reaction included: formation of acyl azide, efficient Curtius rearrangement, nucleophlic addition with amines to produce ureas, cyclization and concurrent cleavage of the resulted six-membered heterocycle from PEG-support in excellent yields

  我们已经开发出一种有效的方法，可以使用聚（乙二醇）作为可溶性聚合物载体来合成各种喹唑啉-2,4-二酮。该反应的程序包括：酰基叠氮化物的形成，有效的库尔修斯重排，与胺的核苷加成以产生脲，环化并同时以优异的产率从PEG-载体上裂解所得的六元杂环。该方法温和且易于操作。
• Small molecule inhibitors of USP1 deubiquitinating enzyme activity
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US10653676B2

  公开（公告）日：2020-05-19

  Provided are small molecule inhibitors of ubiquitin specific protease 1 (USP1) activity and methods for their use in treating and characterizing cancers. The small molecule USP1 inhibitors of the invention are particularly useful in the treatment of cancers that are resistant to DNA cross-linking agents.

  本发明提供了泛素特异性蛋白酶 1（USP1）活性的小分子抑制剂及其用于治疗和鉴定癌症的方法。本发明的小分子 USP1 抑制剂尤其适用于治疗对 DNA 交联剂具有抗药性的癌症。
• An efficient solid phase synthetic route to 1,3-disubstituted 2,4(1H,3H)-Quinazolinediones suitable for combinatorial synthesis
  作者：Adrian L. Smith、Christopher G. Thomson、Paul D. Leeson

  DOI：10.1016/s0960-894x(96)00253-3

  日期：1996.7

  Novel, efficient solid phase chemistry has been developed for the synthesis of 1,3-disubstituted quinazolinediones. Anthranilic acids are linked to a chloroformate resin through the nitrogen, amines are coupled to the free carboxylic acid, and thermal cyclization leads to heterocycle formation and concommitant resin release resulting in traceless linkage. Copyright (C) 1996 Elsevier Science Ltd
• Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems
  作者：Dominik Schwinn、Willi Bannwarth

  DOI：10.1002/1522-2675(200201)85:1<255::aid-hlca255>3.0.co;2-5

  日期：2002.1

  The synthesis of a new perfluoro-tagged benzyloxycarbonyl protecting group is reported, as well as its application in the parallel protection of amines. Isolation of the protected amines was performed by simple liquid-liquid extraction between perfluorinated and organic solvents, Deprotection was achieved by standard hydrogenolysis. The novel protecting group was also applied to cyclization protocols leading to quinazoline-2,4-diones. These products were isolated by simple extraction procedures.