2-cyclohexyl-4-phenyl-1H-imidazole | 111114-70-6

• 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-cyclohexyl-4-phenyl-1H-imidazole
• 英文别名: 2-cyclohexyl-5-phenyl-1H-imidazole
• CAS: 111114-70-6
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: HIDSDCPRZWFCEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环己甲酰氯 在 吡啶 、 dibromobis(triphenylphosphine)nickel(II) 、 sodium sulfate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 2-cyclohexyl-4-phenyl-1H-imidazole
  参考文献：
  名称：

  通过C-C偶联和C-N缩合级联反应进行镍催化的2,4-二取代的咪唑的构建

  摘要：

  开发了一种方便的Ni（II）催化的C-C和C-N级联偶联反应，可直接使用各种2,4-二取代的咪唑。反应范围涵盖了各种芳基和脂肪族取代基，显示出中等至优异的收率。卤素和公差Ñ含杂环基团的演示此方法作进一步的合成探索的多功能性。

  DOI：

  10.1002/adsc.201900096

文献信息

• Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors
  作者：Ian de Toledo、Thiago A. Grigolo、James M. Bennett、Jonathan M. Elkins、Ronaldo A. Pilli

  DOI：10.1021/acs.joc.9b01844

  日期：2019.11.1

  A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol

  基于酮氧化，采用催化HBr和DMSO，然后通过咪唑与醛的缩合反应，开发了一种单罐模块化方法，用于合成2,4（5）-二取代的咪唑。该方法提供了二十九个二取代的NH-咪唑（23％-85％的产率）。通过采用这种氧化-缩合方案，然后在咪唑环中进行溴化和Suzuki偶联，得到三取代的NH-咪唑（23％-69％，三步法），实现了三步合成20种激酶抑制剂的过程。该方法还用于合成已知抑制剂GSK3037619A。
• Substituted 2-cyclohexyl-4-phenyl-1H-imidazole derivatives
  申请人：NEUROGEN CORPORATION

  公开号：US20030144290A1

  公开（公告）日：2003-07-31

  Substituted 2-cyclohexyl-4-phenyl-1H-imidazole derivatives capable of modulating NPY5 receptor activity, are provided. Such compounds may be used to modulate NPY binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  提供了一种能够调节NPY5受体活性的取代2-环己基-4-苯基-1H-咪唑衍生物。这类化合物可用于体内或体外调节NPY与NPY5受体的结合，特别适用于治疗多种疾病（例如，肥胖或贪食症等饮食障碍、精神障碍、糖尿病以及高血压等心血管疾病）在人类、家养伴侣动物和家畜动物中的应用。还提供了用于治疗这些疾病的药物组合物和方法，以及使用这些化合物检测NPY5受体的方法。
• CYCLOHEXANE DERIVATIVE HAVING NPY Y5 RECEPTOR ANTAGONISM
  申请人：Yoshida Hiroshi

  公开号：US20120004227A1

  公开（公告）日：2012-01-05

  The present invention discloses novel cyclohexane derivatives having NPY Y5 receptor antagonistic activity. Specifically, the present invention discloses a compound represented by the formula (I), or a pharmaceutically acceptable salt or a solvate thereof: wherein A is substituted or unsubstituted aryl or heterocyclyl; a combination of X and Y is a combination selected from (X, Y)═(C(═O)N(R 1 ), C(═O)N(R 2 )), (C(═O)N(R 1 ), imidazole-1,3-diyl), (N(R 1 ), C(═O)N(R 2 )), (O, C(═O)N(R 2 )), (C(R 3 )(R 4 ), N(R 2 )) or (a single bond, C(═O)N(R 2 )); R 1 , R 2 and R 3 are independently hydrogen or substituted or unsubstituted alkyl; R 5 is substituted or unsubstituted aryl or heterocyclyl; R 6 is halogen, oxo, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy; m is 0 or 1; and n is an integer of 0 to 5; and B is aromatic carbocycle, monocyclic heterocycle or fused bicyclic heterocycle.

  本发明公开了具有NPY Y5受体拮抗活性的新型环己烷衍生物。具体地，本发明公开了由以下式（I）表示的化合物，或其药学上可接受的盐或溶剂：其中A是取代或未取代的芳基或杂环基；X和Y的组合是从（X，Y）=（C(═O)N(R1)，C(═O)N(R2))，(C(═O)N(R1)，咪唑-1,3-二基)，(N(R1)，C(═O)N(R2))，(O，C(═O)N(R2))，(C(R3)(R4)，N(R2))或（单键，C(═O)N(R2))中选择的组合；R1，R2和R3独立地是氢或取代或未取代的烷基；R5是取代或未取代的芳基或杂环基；R6是卤素、氧代、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基；m为0或1；n为0到5的整数；B是芳香族碳环、单环杂环或融合双环杂环。
• 2,4(5)-Diarylimidazoles: Synthesis and biological evaluation of a new class of sodium channel blockers against hNav1.2
  作者：Mirko Rivara、Aparna R. Baheti、Marco Fantini、Giuseppe Cocconcelli、Chiara Ghiron、Christopher L. Kalmar、Natasha Singh、Ellen C. Merrick、Manoj K. Patel、Valentina Zuliani

  DOI：10.1016/j.bmcl.2008.09.036

  日期：2008.10

  4(5)-diarylimidazoles were prepared through a simple and efficient synthesis and evaluated as potential inhibitors of hNa(v)1.2 sodium channel currents. One member of this series (4) exhibited profound inhibition of Na(v)1.2 currents, emerging as a promising lead compound for further structure-activity relationship studies for the development of novel sodium channel blockers.

  通过简单有效的合成方法制备了少量的新型2,4（5）-二芳基咪唑，并将其评估为hNa（v）1.2钠通道电流的潜在抑制剂。该系列的一个成员（4）表现出对Na（v）1.2电流的强烈抑制作用，作为一种有前途的先导化合物，可用于进一步的结构-活性关系研究，以开发新型钠通道阻滞剂。
• Synthesis of Imidazoles and Pyrimidines Using Palladium-Catalyzed Decar­boxylative Intramolecular Condensation of 1,2,4-Oxadiazol-5(4H)-ones
  作者：Kazuhiro Okamoto、Kouichi Ohe、Takuya Shimbayashi

  DOI：10.1055/s-0034-1378320

  日期：——