2-phenyl-3-(pyrimidin-5-yl)imidazo[1,2-a]pyridine | 1416319-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-3-(pyrimidin-5-yl)imidazo[1,2-a]pyridine
• 英文别名: 2-Phenyl-3-pyrimidin-5-ylimidazo[1,2-a]pyridine；2-phenyl-3-pyrimidin-5-ylimidazo[1,2-a]pyridine
• CAS: 1416319-56-6
• 化学式: C₁₇H₁₂N₄
• 分子量: 272.309
• InChiKey: MZEYDHBMQOXUNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  imidazo[1,2-a]pyridin-2-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 tricyclohexylphosphine tetrafluoroborate 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 三甲基丙酮酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 19.0h， 生成 2-phenyl-3-(pyrimidin-5-yl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents

  摘要：

  A novel series of 2,3-diarylimidazo[1,2-a]pyridines was synthesized and evaluated for their antileishmanial activities. Four derivatives exhibited good activity against the promastigote and intracellular amastigote stages of Leishmania major, coupled with a low cytotoxicity against the HeLa human cell line. The impact of compound lipophilicity on antiparasitic activities was investigated by Log D comparison. Although LmCK1 could be the parasitic target for three compounds (13, 18, 21), the inhibition of another target is under study to explain the antileishmanial effect of the most promising compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.048

文献信息

• Efficient Access to 2,3-Diarylimidazo[1,2-<i>a</i>]pyridines via a One-Pot, Ligand-Free, Palladium-Catalyzed Three-Component Reaction under Microwave Irradiation
  作者：Yuanxiang Wang、Brendan Frett、Hong-yu Li

  DOI：10.1021/ol501136e

  日期：2014.6.6

  ligand-free, Pd(OAc)2-catalyzed, three-component reaction for the synthesis of 2,3-diarylimidazo[1,2-a]pyridines was developed under microwave irradiation. With the high availability of commercial reagents and great efficiency in expanding molecule diversity, this methodology is superior to the existing procedures for the synthesis of 2,3-diarylimidazo[1,2-a]pyridines analogues.

  在微波辐射下，开发了一种快速的单锅、无配体、Pd(OAc) 2催化的三组分反应，用于合成 2,3-二芳基咪唑并[1,2- a ]吡啶。由于商业试剂的高可用性和扩展分子多样性的高效率，该方法优于现有的合成 2,3-二芳基咪唑并[1,2- a ]吡啶类似物的方法。
• Bulky α-diimine palladium complexes: highly efficient for direct C–H bond arylation of heteroarenes under aerobic conditions
  作者：Jia-Sheng Ouyang、Yan-Fang Li、Dong-Sheng Shen、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1039/c6dt02544g

  日期：——

  bidentate N,N-palladium complex C3 with both a backbone and N-aryl bulkiness was found to be a highly efficient precatalyst under aerobic conditions. With a low palladium loading of 0.5–0.1 mol%, a variety of heteroarenes with challenging bulky steric aryl bromides as well as heteroaryl bromides are all applicable for this cross-coupling reaction.

  通过增强主链和N-芳基部分的体积的策略，我们设计并合成了一种体积较大的α-二亚胺钯配合物（即[Ar–N C（R）–C（R）N– Ar] PdCl 2，（Ar ＝ 2-苯甲酰基-4，6-二甲基苯基）}，C1，R ＝ H；C2，R ＝ An；C3，R ＝ Ph）。这些钯配合物的结构已得到很好的表征，而C1和C3则通过X射线衍射进一步表征。对杂芳烃的直接CH键芳构化筛选了预催化剂的催化性能。二齿N，N-钯络合物C3与两个主链和ñ -芳基膨松性被发现是在有氧条件下高效率的预催化剂。钯负载量低至0.5-0.1 mol％，各种具有挑战性的庞大的空间芳基溴化物和杂芳基溴化物的杂芳烃都适用于这种交叉偶联反应。
• Biological evaluation of imidazopyridine derivatives as potential anticancer agents against breast cancer cells
  作者：Bilgesu Onur Sucu

  DOI：10.1007/s00044-022-02984-x

  日期：2022.12

  Imidazo[1,2-a]pyridine cores have increasing importance in the pharmaceutical industry with their wide range pharmacological activities. In this study, two series of imidazopyridine derivatives were synthesized. It was planned to integrate the pyrimidine ring or N-acylhydrazone (NAH) to the carbon atom at the 3 position of the imidazo[1,2-a]pyridine scaffold. Pyrimidine-containing compounds (9–12)

  咪唑并[1,2- a ]吡啶核心因其广泛的药理活性而在制药工业中越来越重要。本研究合成了两个系列的咪唑并吡啶衍生物。计划将嘧啶环或N-酰基腙（NAH）整合到咪唑并[1,2- a ]吡啶支架的3位碳原子上。含嘧啶的化合物 ( 9 – 12 ) 通过钯催化偶联反应 (Suzuki 反应) 和 NAH 化合物 ( 13 – 19) 由 Vilsmeier-Haack 反应合成的醛中间体获得。在乳腺癌细胞中评估了所有衍生物的抗增殖潜力。含嘧啶的化合物在两种乳腺癌细胞系中均未显示出活性结果，而 NAH 衍生物显示出显着的结果。在这些新型衍生物中，化合物15对 MCF7 和 MDA-MB-231 细胞系表现出最有效的活性，IC 50值分别为 1.6 和 22.4 μM。目前的研究表明，这些化合物具有抗癌活性，可用于开发更有效的治疗乳腺癌的化合物。
• Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes
  作者：Bao-Tian Luo、Huan Liu、Zhi-Jie Lin、Jingxing Jiang、Dong-Sheng Shen、Rui-Zhi Liu、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1021/acs.organomet.5b00181

  日期：2015.10.26

  In the present work, a series of alpha-hydroxyimine palladium complexes with bulky substituents (i.e., [Ar-N=C(R)-C(R)(2)-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylinethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.
• Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents
  作者：Sophie Marhadour、Pascal Marchand、Fabrice Pagniez、Marc-Antoine Bazin、Carine Picot、Olivier Lozach、Sandrine Ruchaud、Maud Antoine、Laurent Meijer、Najma Rachidi、Patrice Le Pape

  DOI：10.1016/j.ejmech.2012.10.048

  日期：2012.12

  A novel series of 2,3-diarylimidazo[1,2-a]pyridines was synthesized and evaluated for their antileishmanial activities. Four derivatives exhibited good activity against the promastigote and intracellular amastigote stages of Leishmania major, coupled with a low cytotoxicity against the HeLa human cell line. The impact of compound lipophilicity on antiparasitic activities was investigated by Log D comparison. Although LmCK1 could be the parasitic target for three compounds (13, 18, 21), the inhibition of another target is under study to explain the antileishmanial effect of the most promising compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.