1-phenyl-1H-1,2,3-triazole-4-carbonitrile | 61456-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-1H-1,2,3-triazole-4-carbonitrile
• 英文别名: 4-cyano-1-phenyl-1,2,3-triazole；1-phenyl-1H-[1,2,3]triazole-4-carbonitrile；1-Phenyl-1H-[1,2,3]triazol-4-carbonitril；1-phenyltriazole-4-carbonitrile
• CAS: 61456-87-9
• 化学式: C₉H₆N₄
• 分子量: 170.173
• InChiKey: BKFLGIQLHBKHKO-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C
• 沸点：
  369.6±34.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-1H-1,2,3-triazole-4-carbonitrile 在 氯化亚砜 、 sodium carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 13.0h， 生成 N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-1-phenyl-1H-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors

  摘要：

  A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.035
• 作为产物：
  描述：

  1-苯基-4-甲醇基-1H-1,2,3-三唑 在 manganese(IV) oxide 、 盐酸羟胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 98.0h， 生成 1-phenyl-1H-1,2,3-triazole-4-carbonitrile
  参考文献：
  名称：

  L'abbe, Gerrit; Bruynseels, Maria; Delbeke, Pieter, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2021 - 2027

  摘要：

  DOI：

文献信息

• Flow Hydrodediazoniation of Aromatic Heterocycles
  作者：Liesa Röder、Alexander J. Nicholls、Ian R. Baxendale

  DOI：10.3390/molecules24101996

  日期：——

  Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying

  连续流动加工用于用氢化物快速取代芳族氨基。该方法应用于一系列芳香杂环，证实了该过程的广泛范围和取代基耐受性。使用流动设备并优化工艺以克服在先前依赖批处理程序的研究中限制产率的有问题的不稳定中间体。研究了各种常见的有机溶剂作为潜在的氢化物来源。该方法允许使用纯有机可溶系统以良好的产率对关键结构（例如氨基吡唑和氨基吡啶）进行脱氨基。
• Copper Acetate Catalyzed Regio­selective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide-Alk­ene Cycloaddition/Oxidation Approach
  作者：Sandeep Rohilla、Shyam Sunder Patel、Nidhi Jain

  DOI：10.1002/ejoc.201501301

  日期：2016.2

  A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups (COOR, CONH2, CN, CHO, COR) has been developed. The reaction employs air as the oxidant and does not require any base or additives to afford 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles in good to excellent yields with high regioselectivity

  已开发出乙酸铜催化苄基和芳基叠氮化物与包含吸电子基团（COOR、CONH2、CN、CHO、COR）的末端和内烯烃的氧化环加成反应。该反应使用空气作为氧化剂，不需要任何碱或添加剂，以良好的收率和高区域选择性提供 1,4-二取代和 1,4,5-三取代的 1,2,3-三唑。
• Three-Component Reactions with Sterically Crowded 2,2,4,4-Tetramethyl-3-thioxocyclobutanone, Phenyl Azide, and Electron-Deficient C,C-Dipolarophiles
  作者：Grzegorz Mlosto?、Jaroslaw Roma?nski、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/hlca.19960790507

  日期：1996.8.7

  In order to trap ‘thiocarbonyl-aminides’ A, formed as intermediates in the reaction of thiocarbonyl compounds with phenyl azide, a mixture of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1), phenyl azide, and fumarodinitrile (8) was heated to 80° until evolution of N2 ceased. Two interception products of the ‘thiocarbonylaminide’ A (ArPh) were formed: the known 1,4,2-dithiazolidine 3 (cf. Scheme 1) and

  为了捕获在硫代羰基化合物与叠氮化苯反应中作为中间体形成的``硫代羰基氨基化物'' A，需要使用2,2,4,4-四甲基-3-硫代氧杂环丁酮（1），叠氮化苯和富马腈的混合物（将8）加热至80°，直到N 2的放出停止。形成了两个“硫代羰基氨基化物” A（ArPh）的拦截产物：已知的1,4,2-二噻唑烷3（参见方案1）和新的1,2-噻唑烷12（方案2）。后者的结构通过X射线晶体学确定（图1）。与富马酸二甲酯类似的“三组分反应”（除了已知的拦截产物3和6（方案1）之外，由9）代替8得到了两个意外的产物15和16（方案3），其结构通过X射线晶体学得以阐明（图2）。 。它们的形成是通过重氮化合物的初级[2 + 3]环加成合理化18与1，得到19，接着进一步反应（级联方案4）。
• Redirection of sialic acid metabolism in genetically engineered Escherichia coli
  作者：M. Ringenberg、C. Lichtensteiger、E. Vimr

  DOI：10.1093/glycob/11.7.533

  日期：2001.7.1

  Most microorganisms do not produce sialic acid (sialate), and those that do appear to use a biosynthetic mechanism distinct from mammals. Genetic hybrids of nonpathogenic, sialate-negative laboratory Escherichia coli K-12 strains designed for the de novo synthesis of the polysialic acid capsule from E. coli K1 proved useful in elucidating the genetics and biochemistry of capsule biosynthesis. In this article we propose a dynamic model of sialometabolism to investigate the effects of biosynthetic neu (N-acetylneuraminic acid) and catabolic nan (N-acylneuraminate) mutations on the flux of intermediates through the sialate synthetic pathway. Intracellular sialate concentrations were determined by high pH anion exchange chromatography with pulsed amperometric detection. The results indicated that a strain carrying a null defect in the gene encoding polysialyltransferase (neuS) accumulated > 50 times more CMP–sialic acid than the wild type when strains were grown in a minimal medium supplemented with glucose and casamino acids. Metabolic accumulation of CMP–sialic acid depended on a functional sialic acid synthase (neuB), as shown by the inability of a strain lacking this enzyme to accumulate a detectable endogenous sialate pool. The neuB mutant concentrated trace sialate from the medium, indicating its potential value for quantitative analysis of free sialic acids in complex biological samples. The function of the sialate aldolase (encoded by nanA) in limiting intermediate flux through the synthetic pathway was determined by analyzing free sialate accumulation in neuA (CMP–sialic acid synthetase) nanA double mutants. The combined results demonstrate how E. coli avoids a futile cycle in which biosynthetic sialate induces the system for its own degradation and indicate the feasibility of generating sialooligosaccharide precursors through targeted manipulation of sialate metabolism.

  大多数微生物不产生硅铝酸盐（sialic acid），而那些产生硅铝酸盐的微生物似乎使用了一种与哺乳动物不同的生物合成机制。事实证明，非致病性、对ialate 阴性的实验室大肠杆菌 K-12 株系的基因杂交设计用于从大肠杆菌 K1 中重新合成多聚ialic 酸胶囊，这对阐明胶囊生物合成的遗传学和生物化学非常有用。在这篇文章中，我们提出了一个硅铝酸盐代谢动态模型，以研究生物合成neu（N-乙酰神经氨酸）和分解nan（N-乙酰神经氨酸）突变对硅铝酸盐合成途径中间产物通量的影响。通过高 pH 阴离子交换色谱法和脉冲安培检测法测定了细胞内硅铝酸盐的浓度。结果表明，当菌株在补充了葡萄糖和 casamino 酸的最小培养基中生长时，携带多聚糖基转移酶（neuS）基因缺失的菌株积累的 CMP-sialic酸是野生型的 50 倍以上。CMP-sialic酸的代谢积累依赖于功能性的sialic酸合成酶（neuB），缺乏该酶的菌株无法积累可检测到的内源性sialate池。neuB 突变体从培养基中浓缩了微量的硅铝酸盐，这表明它在定量分析复杂生物样本中游离的硅铝酸盐方面具有潜在价值。通过分析 neuA（CMP-sialic acid synthetase）nanA 双突变体中游离硅铝酸盐的积累，确定了硅铝酸盐醛缩酶（由 nanA 编码）在限制合成途径中间通量方面的功能。综合结果表明了大肠杆菌如何避免生物合成的硅铝酸盐诱导系统自身降解的徒劳循环，并表明了通过有针对性地操纵硅铝酸盐代谢生成硅铝寡糖前体的可行性。
• [DBU][OAc]-mediated synthesis and anthelmintic activity of triazole–tetrazole conjugates
  作者：Madiha A. Siddiqui、Mubarak H. Shaikh、Amol A. Nagargoje、Tarannum T. Shaikh、Vijay M. Khedkar、Prathmesh P. Deshpande、Bapurao B. Shingate

  DOI：10.1007/s11164-022-04842-2

  日期：2022.12

  chemical scaffolds as anthelmintic agents; a series of 1,2,3-triazole–tetrazole conjugates were synthesized. The synthesis of 1,2,3-triazole based tetrazole derivatives has carried out via [2+3]-cycloaddition reaction of triazolyl nitriles with sodium azide. The present design and synthetic strategy offers excellent yields of the products in the presence of [DBU][OAc] under ultrasonic irradiations. The synthesized

  四唑和 1,2,3-三唑的驱虫活性知之甚少。因此，努力将新型化学支架鉴定为驱虫剂。合成了一系列 1,2,3-三唑-四唑偶联物。1,2,3-三唑基四唑衍生物的合成通过三唑基腈与叠氮化钠的[2+3]-环加成反应进行。目前的设计和合成策略在 [DBU][OAc] 存在下在超声波照射下提供了优异的产品产率。通过光谱技术对合成的三唑-四唑缀合物进行表征并筛选它们的驱虫活性。与标准药物阿苯达唑相比，大多数化合物显示出更好的驱虫活性。此外，

表征谱图