N-cyclohexyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-cyclohexyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3-amine
• 化学式: C₁₉H₂₂N₄O
• 分子量: 322.41
• InChiKey: HNIZSCPYGPVDOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  51.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3-amine 、 溴苯 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以72%的产率得到N-cyclohexyl-2-(4-methoxyphenyl)-6-phenylimidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  C–H Bond Functionalization Under Metalation–Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-a]pyrazine

  摘要：

  Concerted metalation deprotonation (CMD) approach with appropriate proton shuttle precursor, base, and solvent (PivOH-K2CO3-toluene) has rendered a regioselective Pd-catalyzed C6-arylation of 3-aminoimidazo[1,2-a]pyrazine, a therapeutically relevant scaffold accessible by multicomponent reaction. The arylation of this heteroarene suffers from competing C5 and C2'-arylation reactions, while the developed process has virtually eliminated these competing arylations. Density functional calculations for CMD C-H activation at C6, C5, C8, and C2' sites imply that the energy barrier with distortion energy penalty as major contributing component influences the regioselectivity.

  DOI：

  10.1021/jo301065s
• 作为产物：
  描述：

  氨基吡嗪 、 异氰环已烷 、 4-甲氧基苯甲醛 在 N-ocetylpyridinium 3-sulfuric acid salt 作用下， 以 乙醇 为溶剂， 以82%的产率得到N-cyclohexyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  静电增强硫酸：一种用于多组分反应的强布朗斯台德酸性催化剂

  摘要：

  一种新的静电增强硫酸作为强 Brønsted 酸性催化剂已被开发用于多组分反应。催化剂中带正电荷的中心通过静电激活它进行酸催化的多组分反应，并在作为绿色溶剂的 EtOH 中在较短的反应时间内和接近室温的时间内提供所需的产物。

  DOI：

  10.1007/s10562-019-02776-w

文献信息

• Ammonium chloride catalyzed one-pot synthesis of imidazo[1,2-a]pyridines
  作者：Ahmad Shaabani、Fahimeh Rezazadeh、Ebrahim Soleimani

  DOI：10.1007/s00706-008-0872-x

  日期：2008.8

  Ammonium chloride as a very inexpensive and readily available reagent efficiently catalyzes one-pot, three-component Groebke condensation reactions of aldehydes, isocyanides, and 2-aminopyridines or 2-aminopyrimidines in methanol to afford the corresponding imidazo[1,2- a ]pyridines in high yields at room temperature.

  氯化铵是一种非常便宜且易于获得的试剂，可有效催化醛，异氰酸酯和2-氨基吡啶或2-氨基嘧啶在甲醇中的一锅三组分 Groebke 缩合反应，得到相应的咪唑并[1,2- a ]吡啶在室温下高产量。
• [EN] SMALL MOLECULE INHIBITION OF TRANSCRIPTION FACTOR SALL4 AND USES THEREOF<br/>[FR] INHIBITION PAR DES PETITES MOLÉCULES DU FACTEUR DE TRANSCRIPTION SALL4 ET SES UTILISATIONS
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2019070943A1

  公开（公告）日：2019-04-11

  Provided herein are compounds that interrupt the function of SALL4. Also described are pharmaceutical compositions and medical uses of these compounds.

  本文提供了一些干扰SALL4功能的化合物。同时还描述了这些化合物的药物组合物和医疗用途。
• Small molecule inhibition of transcription factor SALL4 and uses thereof
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US11530209B2

  公开（公告）日：2022-12-20

  Provided herein are compounds that interrupt the function of SALL4. Also described are pharmaceutical compositions and medical uses of these compounds.

  本文提供了能干扰 SALL4 功能的化合物。还描述了这些化合物的药物组合物和医疗用途。
• Combinatorial Discovery of Fluorescent Pharmacophores by Multicomponent Reactions in Droplet Arrays
  作者：Olga N. Burchak、Laurent Mugherli、Mariano Ostuni、Jean Jacques Lacapère、Maxim Y. Balakirev

  DOI：10.1021/ja204016e

  日期：2011.7.6

  Fluorescence imaging in clinical diagnostics and biomedical research relies to a great extent on the use of small organic fluorescent probes. Because of the difficulty of combining fluorescent and molecular-recognition properties, the development of such probes has been severely restricted to a number of well-known fluorescent scaffolds. Here we demonstrate that autofluorescing druglike molecules are a valuable source of bioimaging probes. Combinatorial synthesis and screening of chemical libraries in droplet microarrays allowed the identification of new types of fluorophores. Their concise and clean assembly by a multicomponent reaction presents a unique potential for the one-step synthesis of thousands of structurally diverse fluorescent molecules. Because they are based upon a druglike scaffold, these fluorophores retain their molecular recognition potential and can be used to design specific imaging probes.
• One-Pot Three-Component Synthesis of 3-Aminoimidazo[1,2-a]pyridines and -pyrazines in the Presence of Silica Sulfuric Acid
  作者：Ahmad Shaabani、Ebrahim Soleimani、Ali Maleki

  DOI：10.1007/s00706-006-0561-6

  日期：2007.1

  The synthesis of 3-aminoimidazo[1,2-a]pyridines and 3-aminoimidazo[1,2-a]pyrazines through a condensation reaction of 2-aminopyridine or 2-aminopyrazine, aldehyde, and alkyl or aryl isocyanide in high yields at room temperature in the presence of silica sulfuric acid is described.