4-chloro-1-methylimidazo[1,2-a]quinoxaline | 191349-73-2

• 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: 4-chloro-1-methylimidazo[1,2-a]quinoxaline
• CAS: 191349-73-2
• 化学式: C₁₁H₈ClN₃
• 分子量: 217.658
• InChiKey: JYJHXLBINQTWJT-UHFFFAOYSA-N

物化性质

• 沸点：
  349.7±42.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-1-methylimidazo[1,2-a]quinoxaline 在 氨 作用下， 生成 1-methylimidazo[1,2-a]quinoxaline-4-amine
  参考文献：
  名称：

  咪唑[1,2-a]喹喔啉衍生物作为针对植物病原真菌的潜在抗真菌剂的合成和评价

  摘要：

  为了发现新颖有效的潜在农业抗真菌剂，设计了各种咪唑[1,2-a]喹喔啉衍生物，并用现有和廉价的试剂合成。首先针对 10 种典型的植物病原真菌评估了它们的抗真菌活性。体外抗真菌活性表明，一些化合物比两种市售杀菌剂百菌清和噻沙唑表现出更明显的广谱杀菌活性。Mali 和 Botrytis cinerea 菌株对 10 多种化合物的 EC50 值为 1.4-27.0 μg/mL，表现出最高的敏感性。化合物 5c 和 5f 分别对苹果笙草 （EC50 = 5.6 μg/mL） 和茄子镰刀菌 （EC50 = 5.1 μg/mL） 显示出最有希望的抑制作用。关于作用机制的初步研究表明，咪唑[1,2-a]喹喔啉骨架可能通过破坏菌丝分化、孢子萌发和胚芽管生长来发挥其抗真菌作用。此外，细胞实验结果表明，这些靶标化合物对 BV2 细胞具有良好的安全性。总体而言，化合物 5c 和 5f 可以被认为是针对特定真菌的

  DOI：

  10.1007/s11030-023-10739-y
• 作为产物：
  描述：

  1-methylimidazo[1,2-a]quinoxalin-4-(5H)-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 生成 4-chloro-1-methylimidazo[1,2-a]quinoxaline
  参考文献：
  名称：

  Imidazo[1,2-a]quinoxalin-4-amines: A novel class of nonxanthine A1-adenosine receptor antagonists

  摘要：

  The syntheses and A(1) adenosine receptor affinities of a number of imidazo[1,2-alpha]quinoxalin-4-amines are reported. Structure activity relationships within the series and in comparison with other similar tricyclic nonxanthine adenosine antagonists are discussed, leading to a putative common binding mode of these nitrogen-containing heterocycles to A(1) adenosine receptors. Secondary amino compounds displayed the best affinities toward A(1) receptors, while the tertiary amines were almost devoid of activity, thus suggesting a crucial role for the hydrogen bond-forming 4-NH group. Remarkably higher potencies for l-methyl and N-cyclopentyl derivatives were also found. 4-Cyclopentylamino-1-methylimidazo[1,2-alpha]quinoxaline (IRFI 165) is the most potent compound in this series, having K-i(A(1)) = 7.9 nM. It is also provided with a good A(1) selectivity both versus A(2a) and A(3) subtypes and was selected for further pharmacological studies. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80019-1

文献信息

• Imidazo[1,2-a]quinoxalines: synthesis and cyclic nucleotide phosphodiesterase inhibitory activity
  作者：Stéphanie Parra、Florence Laurent、Guy Subra、Carine Deleuze-Masquefa、Veronique Benezech、Jean-Roch Fabreguettes、Jean-Pierre Vidal、Tristan Pocock、Keith Elliott、Roger Small、Roger Escale、Alain Michel、Jean-Pierre Chapat、Pierre-Antoine Bonnet

  DOI：10.1016/s0223-5234(01)01213-2

  日期：2001.3

  A group of imidazo[1,2-a]quinoxalines have been synthesised from quinoxaline by condensation of an appropriate haloester or intramolecular cyclisation of a keto moiety on an intracyclic nitrogen atom. The reactivity of the heterocycle was explored through diverse reactions such as electrophilic substitution, lithiation and halogen-metal exchange to give access to a new series of derivatives. Confirmation of their structure was mainly performed by NMR, after careful assignment of the signals in comparison to previous attributions made on the parent imidazo[1,2-a]quinoxaline and discussion of available data in the literature. The cyclic nucleotide phosphodiesterase inhibitor activity of some of these derivatives has been assessed on isoenzymes type III and type IV. Compound 15, 4-(methylamino)imidazo[1,2-a]quinoxaline-2-carbonitrile, exhibited potent relaxant activity on smooth muscle, with a potency similar to the one measured with SCA 40, its structural analogue in the imidazo[1,2-a]pyrazine series. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• US6124287
  申请人：——

  公开号：——

  公开（公告）日：——
• US06124287
  申请人：——

  公开号：——

  公开（公告）日：——
• IMIDAZO[1,2-a]QUINOXALIN-4-AMINES ACTIVE AS ADENOSINE ANTAGONISTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：Biomedica Foscama Industria Chimico-Farmaceutica S.p.A.

  公开号：EP0865442B1

  公开（公告）日：2000-07-05
• US6124287A
  申请人：——

  公开号：US6124287A

  公开（公告）日：2000-09-26