(4aS,8aS)-4a,5,6,7,8,8a-hexahydro-2-quinoxalinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4aS,8aS)-4a,5,6,7,8,8a-hexahydro-2-quinoxalinone
• 英文别名: (4aS,8aS)-4a,5,6,7,8,8a-hexahydroquinoxalin-2(1H)-one；(4aS,8aS)-4a,5,6,7,8,8a-hexahydro-1H-quinoxalin-2-one
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: LHRGOVPAWZDMDA-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aS,8aS)-4a,5,6,7,8,8a-hexahydro-2-quinoxalinone 在 重水 作用下， 生成 trans-4a,5,6,8,8a-hexahydro-1H-quinoxalin-2-one
  参考文献：
  名称：

  Imines that React with Phenols in Water over a Wide pH Range

  摘要：

  Cyclic imine derivatives that react with phenols, including tyrosine residues of peptides, have been developed. Reactions of the imines with phenols proceeded in water over a wide pH range (pH 2-10) at room temperature to 37 degrees C and afforded Mannich products without the need of additional catalysts.

  DOI：

  10.1021/jo8017389
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 、 trans-1,2-Diaminocyclohexane 以 异丙醇 、 甲苯 为溶剂， 反应 2.0h， 以99%的产率得到(4aS,8aS)-4a,5,6,7,8,8a-hexahydro-2-quinoxalinone
  参考文献：
  名称：

  Imines that React with Phenols in Water over a Wide pH Range

  摘要：

  Cyclic imine derivatives that react with phenols, including tyrosine residues of peptides, have been developed. Reactions of the imines with phenols proceeded in water over a wide pH range (pH 2-10) at room temperature to 37 degrees C and afforded Mannich products without the need of additional catalysts.

  DOI：

  10.1021/jo8017389

文献信息

• Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives
  作者：István Szatmári、Petra Barta、Gábor Tóth、Attila Balázs、Judit Halász、Ferenc Fülöp

  DOI：10.1002/ejoc.201700699

  日期：2017.10.10

  synthesized via an o-quinone methide intermediates. The enantiopure annelational analogues naphth[1,3]oxazino[3,4-a]quinoxalinone derivatives have also been prepared by a different synthetic pathway. The conformational behaviour of the new polyheterocycles was examined and confirmed by theoretical calculations.

  新的非外消旋萘[1,3]恶嗪基[3,2- a ]喹喔啉酮是通过邻醌甲基化物中间体合成的。对映体纯净的延髓类似物萘[1,3]恶嗪基[3,4- a ]喹喔啉酮衍生物也已通过不同的合成途径制备。研究了新的多杂环的构象行为，并通过理论计算证实了这一点。
• Copper-Catalyzed Oxidative [3 + 2]-Annulation of Quinoxalin-2(1<i>H</i>)-one with Oxime Esters toward Functionalized Pyrazolo[1,5-<i>a</i>]quinoxalin-4(5<i>H</i>)-ones as Opioid Receptor Modulators
  作者：Anamika Yadav、Anubhav Yadav、Shashank Tripathi、Varun Dewaker、Ruchir Kant、Prem Narayan Yadav、Ajay Kumar Srivastava

  DOI：10.1021/acs.joc.2c00563

  日期：2022.6.3

  Pyrazolo[1,5-a]quinoxalin-4(5H)-one derivatives as novel opioid receptor modulators have been synthesized via copper-catalyzed oxidative [3 + 2]-annulation of quinoxalin-2(1H)-one and oxime-O-acetates. This hydrazine-free C–C and N–N bond formation strategy starts with the generation of C2N1 synthon using oxime acetate, which reacts in a [3 + 2] manner with quinoxalin-2(1H)-one, followed by oxidative

  Pyrazolo[1,5 - a ]quinoxalin-4( 5H )-one 衍生物作为新型阿片受体调节剂已通过铜催化氧化 [3 + 2]-quinoxalin-2( 1H )-one 和肟的环化合成- O-乙酸盐。这种不含肼的 C-C 和 N-N 键形成策略始于使用乙酸肟生成 C 2 N 1合成子，其以 [3 + 2] 方式与 quinoxalin-2(1 H )-one 反应，随后通过氧化芳构化。合成的化合物针对阿片受体进行了测试，其中八种化合物与 EC 50具有拮抗作用< 5 μM 在各种阿片受体上。进行分子对接研究以确定活性 pyrazolo[1,5 - a ]quinoxalin-4(5 H )-one 配体与 hKOR 蛋白的结合。对接结果表明化合物3d和3g与活性位点口袋残基T111的羟基参与氢键结合。
• MDR-reversing 8-hydroxy-quinoline derivatives
  申请人：MAGYAR TUDOMÁNYOS AKADÉMIA TERMÉSZETTUDOMÁNYI KUTATÓKÖZPONT

  公开号：US10744127B2

  公开（公告）日：2020-08-18

  The present invention is related to 8-hydroxy-quinoline derivatives having multidrug-resistance reversing activity with improved selectivity and increased cytotoxicity towards multidrug-resistant cancer cells, preparation thereof and use of the same in the treatment of cancer, especially multidrug-resistant variants thereof.

  本发明涉及具有多药耐药性逆转活性的 8-羟基喹啉衍生物，其选择性提高，对多药耐药性癌细胞的细胞毒性增强，本发明的制备方法及其在治疗癌症，特别是癌症的多药耐药性变体中的应用。
• MDR-REVERSING 8-HYDROXY-QUINOLINE DERIVATIVES
  申请人：MAGYAR TUDOMÁNYOS AKADÉMIA TERMÉSZETTUDOMÁNYI KUTATÓKÖZPONT

  公开号：US20190151306A1

  公开（公告）日：2019-05-23

  The present invention is related to 8-hydroxy-quinoline derivatives having multidrug-resistance reversing activity with improved selectivity and increased cytotoxicity towards multidrug-resistant cancer cells, preparation thereof and use of the same in the treatment of cancer, especially multidrug-resistant variants thereof.
• [EN] MDR-REVERSING 8-HYDROXY-QUINOLINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 8-HYDROXY-QUINOLÉINE INVERSANT LA MULTIRÉSISTANCE AUX MÉDICAMENTS
  申请人：MAGYAR TUDOMÁNYOS AKADÉMIA TERMÉSZETTUDOMÁNYI KUTATÓKÖZPONT

  公开号：WO2017175018A2

  公开（公告）日：2017-10-12

  The present invention is related to 8-hydroxy-quinoline derivatives having multidrug-resistance reversing activity with improved selectivity and increased cytotoxicity towards multidrug-resistant cancer cells, preparation thereof and use of the same in the treatment of cancer, especially multidrug-resistant variants thereof.