1-(3-cyanophenyl)-4-(pyridin-3-yl)-1H-1,2,3-triazole | 1215004-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3-cyanophenyl)-4-(pyridin-3-yl)-1H-1,2,3-triazole
• 英文别名: 3-(4-pyridin-3-yl-[1,2,3-triazol-1-yl])-benzonitrile；3-(4-Pyridin-3-yl-[1,2,3]triazol-1-yl)-benzonitrile；3-(4-pyridin-3-yltriazol-1-yl)benzonitrile
• CAS: 1215004-86-6
• 化学式: C₁₄H₉N₅
• 分子量: 247.259
• InChiKey: KEUQOMRNFOFARU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间氨基苯甲腈 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 0.58h， 生成 1-(3-cyanophenyl)-4-(pyridin-3-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  TRIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS

  摘要：

  这项发明涉及新型三唑衍生物，发现它们是尼古丁型乙酰胆碱受体的调节剂。由于其药理特性，本发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱系统、外周神经系统（PNS）、平滑肌收缩有关的疾病或紊乱，内分泌疾病或紊乱，神经退行性疾病或紊乱，炎症相关的疾病或紊乱，疼痛以及由于滥用化学物质终止而引起的戒断症状等多种疾病或紊乱具有用处。

  公开号：

  US20110212999A1

文献信息

• Synthesis and activity of substituted heteroaromatics as positive allosteric modulators for α4β2α5 nicotinic acetylcholine receptors
  作者：Zhuang Jin、Pasha Khan、Youseung Shin、Jingyi Wang、Li Lin、Michael D. Cameron、Jon M. Lindstrom、Paul J. Kenny、Theodore M. Kamenecka

  DOI：10.1016/j.bmcl.2013.11.049

  日期：2014.1

  The design and synthesis of a series of substituted heteroaromatic α4β2α5 positive allosteric modulators is reported. The optimization and development of the heteroaromatic series was carried out from NS9283, and several potent analogues, such as 3-(5-(pyridin-3-yl)-2H-tetrazol-2-yl)benzonitrile (5k) and 3,3′-(2H-tetrazole-2,5-diyl)dipyridine (12h) with good in vitro efficacy were discovered.

  报道了一系列取代的杂芳族 α4β2α5 正变构调节剂的设计和合成。杂芳族系列的优化和开发是从 NS9283 和几个有效的类似物，如 3-(5-(pyridin-3-yl)-2 H -tetrazol-2-yl)benzonitrile ( 5k ) 和 3,发现了具有良好体外功效的3'-(2 H-四唑-2,5-二基)二吡啶( 12h )。
• TRIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
  申请人：NeuroSearch A/S

  公开号：EP2324007B1

  公开（公告）日：2012-08-15
• [EN] TRIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE TRIAZOLE ET LEUR UTILISATION EN TANT QUE MODULATEURS DE RÉCEPTEUR NICOTINIQUE D'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2010026134A1

  公开（公告）日：2010-03-11

  This invention relates to novel triazole derivatives, which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.
• Synthesis of Deuterated 1,2,3-Triazoles
  作者：Hari K. Akula、Mahesh K. Lakshman

  DOI：10.1021/jo301146j

  日期：2012.10.19

  The copper-catalyzed azide alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D+ ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.