2,3-diphenylimidazo[1,2-a]pyrimidine | 909104-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-diphenylimidazo[1,2-a]pyrimidine
• CAS: 909104-02-5
• 化学式: C₁₈H₁₃N₃
• 分子量: 271.321
• InChiKey: HDQHDZJYEPGVKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-diphenylimidazo[1,2-a]pyrimidine 在 一水合肼 作用下， 反应 0.25h， 以94 mg的产率得到4,5-diphenyl-1H-imidazol-2-amine
  参考文献：
  名称：

  新型Combretastatin-2-氨基咪唑类似物作为有效的微管蛋白组装抑制剂：桥接骨架和芳基部分的独特药理作用探索

  摘要：

  磷酸盐和丝氨酸前药形式的Combretastatin A-4（CA-4）正在进行II期临床试验。由于我们对发现受CA-4启发的新化学实体的兴趣，通过涉及原子经济型芳烃C–H键芳基化的有效且多样化的可行途径，设计和合成了该化合物的一系列新的4,5-二芳基-2-氨基咪唑类似物。有趣的是，四种化合物在纳摩尔浓度下均显示出有效的基于细胞的抗增殖活性。在这些化合物中，化合物12比CA-4更有效地抑制了几种癌细胞的增殖。它使微管解聚，诱发纺锤体缺陷，并使细胞中的有丝分裂停滞。化合物12与微管蛋白结合并在体外抑制微管蛋白的聚合。另外，鬼臼毒素和CA-4抑制化合物12与微管蛋白的结合。探索了桥接基序以及喹啉核的独特药效学特征。我们还注意到化合物12作为表征新CA-4类似物的潜在探针的宝贵品质。

  DOI：

  10.1021/acs.jmedchem.6b00101
• 作为产物：
  描述：

  3,4-Diphenylisoxazol-5(2H)-one 以 neat (no solvent) 为溶剂， 140.0~540.0 ℃ 、6.67 Pa 条件下， 反应 2.17h， 生成 2,3-diphenylimidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  Synthesis of Heterocyclic-fused Imidazoles by Pyrolysis of N-Heterocyclic Isoxazol-5(2H)-ones

  摘要：

  通过亚氨基羰基中间体对 N-杂环异恶唑-5(2H)-酮进行闪速真空热解（FVP），实现了杂环融合咪唑的合成。与由三唑生成的亚氨基羰基化合物不同，目前的合成方法没有观察到结构重排。我们还证明，挥发性较低的异噁唑-5(2H)-酮衍生物可通过凝聚相热解生成相应的咪唑类化合物。

  DOI：

  10.1071/ch14119

文献信息

• Structure−Activity Relationship of 4(5)-Aryl-2-amino-1<i>H</i>-imidazoles, <i>N</i>1-Substituted 2-Aminoimidazoles and Imidazo[1,2-<i>a</i>]pyrimidinium Salts as Inhibitors of Biofilm Formation by <i>Salmonella</i> Typhimurium and <i>Pseudomonas aeruginosa</i>
  作者：Hans P. L. Steenackers、Denis S. Ermolat’ev、Bharat Savaliya、Ami De Weerdt、David De Coster、Anamik Shah、Erik V. Van der Eycken、Dirk E. De Vos、Jozef Vanderleyden、Sigrid C. J. De Keersmaecker

  DOI：10.1021/jm1011148

  日期：2011.1.27

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.
• CONDENSED-CYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE COMPRISING THE SAME, AND FLAT PANEL DISPLAY APPARATUS
  申请人：Kim Hee-Yeon

  公开号：US20120286246A1

  公开（公告）日：2012-11-15

  A condensed-cyclic compound represented by Formula 1 below, an organic light-emitting device including the same, and a flat panel display apparatus including the organic light-emitting device: Wherein, X 1 , Ar 1 Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , and Ar 12 are described in the detailed description of the invention. The organic light-emitting device including an organic layer including the compound above has low driving voltage and high emission efficiency.
• US9012042B2
  申请人：——

  公开号：US9012042B2

  公开（公告）日：2015-04-21
• Novel Combretastatin-2-aminoimidazole Analogues as Potent Tubulin Assembly Inhibitors: Exploration of Unique Pharmacophoric Impact of Bridging Skeleton and Aryl Moiety
  作者：Vikas Chaudhary、Jubina B. Venghateri、Hemendra P. S. Dhaked、Anil S. Bhoyar、Sankar K. Guchhait、Dulal Panda

  DOI：10.1021/acs.jmedchem.6b00101

  日期：2016.4.14

  Among the compounds, compound 12 inhibited the proliferation of several types of cancer cells much more efficiently than CA-4. It depolymerized microtubules, induced spindle defects, and stalled mitosis in cells. Compound 12 bound to tubulin and inhibited the polymerization of tubulin in vitro. In addition, podophyllotoxin and CA-4 inhibited the binding of compound 12 to tubulin. The distinctive pharmacophoric

  磷酸盐和丝氨酸前药形式的Combretastatin A-4（CA-4）正在进行II期临床试验。由于我们对发现受CA-4启发的新化学实体的兴趣，通过涉及原子经济型芳烃C–H键芳基化的有效且多样化的可行途径，设计和合成了该化合物的一系列新的4,5-二芳基-2-氨基咪唑类似物。有趣的是，四种化合物在纳摩尔浓度下均显示出有效的基于细胞的抗增殖活性。在这些化合物中，化合物12比CA-4更有效地抑制了几种癌细胞的增殖。它使微管解聚，诱发纺锤体缺陷，并使细胞中的有丝分裂停滞。化合物12与微管蛋白结合并在体外抑制微管蛋白的聚合。另外，鬼臼毒素和CA-4抑制化合物12与微管蛋白的结合。探索了桥接基序以及喹啉核的独特药效学特征。我们还注意到化合物12作为表征新CA-4类似物的潜在探针的宝贵品质。
• Synthesis of Heterocyclic-fused Imidazoles by Pyrolysis of N-Heterocyclic Isoxazol-5(2H)-ones
  作者：Steven-Alan G. Abel、Mathew O. Eglinton、James K. Howard、Dylan J. Hunt、Rolf H. Prager、Jason A. Smith

  DOI：10.1071/ch14119

  日期：——

  The synthesis of heterocyclic-fused imidazoles was achieved by flash vacuum pyrolysis (FVP) of N-heterocyclic isoxazol-5(2H)-ones via an iminocarbene intermediate. Unlike iminocarbenes generated from triazoles, no structural rearrangements were observed during the current synthesis method. We also demonstrated that less volatile isoxazol-5(2H)-one derivatives yield the corresponding imidazoles by condensed phase pyrolysis.

  通过亚氨基羰基中间体对 N-杂环异恶唑-5(2H)-酮进行闪速真空热解（FVP），实现了杂环融合咪唑的合成。与由三唑生成的亚氨基羰基化合物不同，目前的合成方法没有观察到结构重排。我们还证明，挥发性较低的异噁唑-5(2H)-酮衍生物可通过凝聚相热解生成相应的咪唑类化合物。