4,5-dicyano-1-(phenylmethyl)-1H-imidazole | 123124-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dicyano-1-(phenylmethyl)-1H-imidazole
• 英文别名: 1-benzyl-4,5-dicyanoimidazole；N-benzyl-4,5-dicyanoimidazole；1-benzyl-1H-imidazole-4,5-dicarbonitrile；1-benzylimidazole-4,5-dicarbonitrile
• CAS: 123124-90-3
• 化学式: C₁₂H₈N₄
• 分子量: 208.222
• InChiKey: RPKGFMRUOIMQNM-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  493.6±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dicyano-1-(phenylmethyl)-1H-imidazole 在 sodium hydroxide 、 乙酸酐 作用下， 反应 2.42h， 生成 1-苄基咪唑-5-羧酸
  参考文献：
  名称：

  Synthesis of 1-benzyl-8,9-dihydroimidazo[4,5-c]pyrrolo[3,2-g]quinolin-4(5H)-one via palladium-catalyzed intramolecular arylation

  摘要：

  The synthesis of a novel tetracyclic structure, 8,9-dihydroimidazo[4,5-c]pyrrolo[3,2-g]quinolin-4(5H)-one, has been achieved by a convergent pathway. Coupling of the weakly nucleophilic hindered aromatic amine with 1-benzylimidazole-4-carboxylic acid, 7, afforded the corresponding amide 9 using a DCP/DMF complex; subsequent Heck-type arylation leading to desired tetracyclic molecule imidazo[4,5-c]-pyrrolo[3,2-g]quinolin-4(5H)-one. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.05.067
• 作为产物：
  描述：

  4,5-二氰基咪唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-dicyano-1-(phenylmethyl)-1H-imidazole
  参考文献：
  名称：

  含有5：7稠合的4,6,8-三氨基咪唑并[4,5- e ] [1,3]二氮杂ring环系统的化合物的合成，抗癌活性和SAR分析

  摘要：

  本文描述的是我们对5：7稠合杂环（1）的有限结构-活性关系（SAR）研究，该杂环包含4,6,8-三氨基咪唑并[4,5- e ] [1,3]二氮杂pine环系统，我们在几年前报道了其合成和有效的广谱抗癌活性。我们在这项研究中的SAR努力主要集中在杂环的N-1和N 6位上取代基的合法连接上。我们的结果表明，在杂环的N-1位上连接的取代基与在杂环的N 6位上连接的取代基之间存在一些微妙的相关性。在靶蛋白上可能有一个常见的疏水结合口袋，被N-1和N 6处的取代基所占据杂环配体的-位。该口袋似乎足够大，可以容纳N 6的C-18烷基链，而在N-1处没有任何连接，或者在N 6处具有结合的C-10，在N-1处具有CH 2 Ph。在N 6处短于或长于C-10且在N-1处连接有CH 2 Ph的任何烷基链会导致生物活性降低。

  DOI：

  10.1016/j.bmc.2016.03.015

文献信息

• Synthesis and cardiotonic activity of novel biimidazoles
  作者：Donald P. Matthews、James R. McCarthy、Jeffrey P. Whitten、Philip R. Kastner、Charlotte L. Barney、Franklin N. Marshall、Marcia A. Ertel、Therese Burkhard、Philip J. Shea、Takashi Kariya

  DOI：10.1021/jm00163a052

  日期：1990.1

  A series of substituted 2,2'-bi-1H-imidazoles and related analogues was synthesized and evaluated for inotropic activity. Structure-activity relationship studies based on a nonclassical bioisosteric approach indicated the necessity of a cyano group on one of the imidazole rings to obtain the desired pharmacological profile. 4(5)-Cyano-2,2'-bi-1H-imidazole (15a) was the most potent inotropic agent in

  合成了一系列取代的2,2'-bi-1H-咪唑和相关类似物，并评估了其正性肌力。基于非经典生物等位线方法的结构活性关系研究表明，咪唑环之一上的氰基必须具有所需的药理特性。4（5）-Cyano-2,2'-bi-1H-咪唑（15a）是该系列中最有效的正性肌力药。在麻醉狗中，0.16 mg / kg iv时左心室dP / dt增加25％（ED25％= 0.16 mg / kg），在1 mg / kg iv时左心室收缩力增加60％。化合物15a是分离自犬心的IV型环状核苷酸磷酸二酯酶的良好抑制剂，具有与氨力农相似的效力。5'-cyano-2,4'-bi-1H-咪唑（44）和4-cyano-2,4' -bi-1H-咪唑（48）具有正性肌力活性。另外，两种可能的1,1'-二甲基氰基-2,2'-bi-1H-咪唑（24和25）是不活泼的，表明酸性NH和氰基对于正性肌力活性至关重要。
• Ring expanded nucleosides and nucleotides
  申请人：——

  公开号：US20040077564A1

  公开（公告）日：2004-04-22

  The present invention relates to compositions comprising analogues of purine nucleosides containing a ring-expanded (“fat”) heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such compositions, as well as methods of use thereof. In particular, these compositions may be utilized in the treatment of certain cancers, bacterial, fungal, parasitic, and viral infections, including, but not limited to, Acquired Immunodeficiency Syndrome (AIDS), hepatitis, Epstein-Barr and cytomegalovirus.

  本发明涉及含有环扩张（“肥胖”）杂环环代替嘌呤的嘌呤核苷类似物和未经改性或改性的糖残基的组合物，以及这些组合物的药学上可接受的衍生物，以及其使用方法。特别地，这些组合物可用于治疗某些癌症、细菌、真菌、寄生虫和病毒感染，包括但不限于获得性免疫缺陷综合症（AIDS）、肝炎、EB病毒和巨细胞病毒。
• A Short Synthesis of a Novel Ring-Expanded Purine and Its Nucleoside Analogue Containing the Imidazo[4,5-<i>e</i>][1,3]diazepine Ring Skeleton with Multiple Amino Substituents Attached to the 7-Membered Ring
  作者：L. Wang、A. Bhan、R. S. Hosmane、R. D. Guiles

  DOI：10.1080/15257779408013222

  日期：1994.12

  The synthesis of 4,6,8-triaminoimidazo[4,5-e][1,3]diazepine (1) and its nucleoside analogue (6) are reported. The heterocycle was prepared in a single step by condensation of 4,5-dicyanoimidazole with guanidine. The 5,7-fused ring structure of 1 was distinguished from the other possible 5:5-fused isomer 2 by preparing the N-15-labeled heterocycle (1*) and exploring its N-15-H-1 coupling patterns in both H-1 and N-15 NMR spectra. These spectral patterns also enabled establishment of the triamino tautomeric form of 1 as assigned. Compound 1, a novel ring-expanded (''fat'') analogue of purine, is anticipated to be planar and aromatic as predicted by molecular modeling. The 1-benzyl analogue (4), a protocol for the ribosyl analogue 6, was similarly prepared from 1-benzyl-4,5-dicyanoimidazole. The nucleoside 6 was prepared by the modified Vorbruggen ribosylation of 1. The position of ribosylation was unequivocally established by an unambiguous synthesis of 6 from condensation of 1-(2',3',5'-tri-O-benzoyl-beta-($) under bar D-ribofuranosyl)-4,5-dicyanoimidazole (7) with guanidine in a solution of sodium methoxide in methanol. The nucleoside 7 was prepared by the Vorbruggen ribosylation of 4,5-dicyanoimidazole.
• Ring-expanded nucleosides and nucleotides
  申请人：Nabi

  公开号：EP1227103B1

  公开（公告）日：2006-07-26
• Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes
  作者：L. Oresmaa、H. Kotikoski、M. Haukka、O. Oksala、E. Pohjala、H. Vapaatalo、E. Moilanen、P. Vainiotalo、P. Aulaskari

  DOI：10.1016/j.ejmech.2006.05.001

  日期：2006.9

  Novel 1-R-imidazole-5-amidoximes and I-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observing the stimulation of formation of cyclic guanosine-3',5'-monophosphate (cGMP) in the incubation of porcine iris-ciliary body. In the incubation experiments, 1-methylimidazole-5-amidoxime and 1(H)-imidazole-4(5)-amidoxime stimulated formation of cGMP indicating NO donating ability of these compounds. 1-Methylimidazole-5-amidoxime lowered IOP significantly after intravitreal injection. (c) 2006 Elsevier SAS. All rights reserved.