2-azido-1-(piperidin-1-yl)ethanone | 1132647-39-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-azido-1-(piperidin-1-yl)ethanone
• 英文别名: 2-azido-1-(piperidin-1-yl)ethan-1-one；2-azido-1-piperidin-1-ylethanone
• CAS: 1132647-39-2
• 化学式: C₇H₁₂N₄O
• mdl: MFCD14652219
• 分子量: 168.198
• InChiKey: VLKMRAIOOAUYJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azido-1-(piperidin-1-yl)ethanone 在 盐酸 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 8.0h， 生成 4-[({4-[2-oxo-2-(piperidin-1-yl)ethyl]-1H-1,2,3-triazol-1-yl}methyl)amino]quinoline-7-carbonitrile
  参考文献：
  名称：

  In vitro antimalarial activity, β-haematin inhibition and structure–activity relationships in a series of quinoline triazoles

  摘要：

  A novel series of quinoline triazole amide analogues (38-51) has been synthesized. Analogues 38-44 had a Cl substituent at the 7-position of the quinoline ring, while 45-51 had a CN substituent at this position. Compounds 40,45 and 49 were found to be the most active in the series against the Plasmodium falciparum chloroquine-sensitive D10 strain, with IC50 values in the range of 349-1247 nM, with 40 and 45, but not 49 also exhibiting similar activity against the chloroquine-resistant 1(1 strain of parasite. Quinoline triazoles 40 and 44 were the most active beta-haematin inhibitors, with 50% inhibitory concentrations of 14.7 and 8.9 1tM respectively. In vitro antimalarial activity of the 7-C1 bearing analogues 38 -44 exhibited a strong linear dependence of log(1/IC50) on log P. Thus, the more lipophilic, the more active it was found be. The 7-CN series 45-51 showed no such dependence. The resistance index (IC50 K1 /IC50 D10) also exhibited a linear dependence on log P, with a substantially steeper slope in the case of the 7-CI series. The findings demonstrate the feasibility of producing hydrophilic analogues with strong activity and low cross-resistance with chloroquine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.046
• 作为产物：
  描述：

  1-(溴乙酰基)哌啶 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-azido-1-(piperidin-1-yl)ethanone
  参考文献：
  名称：

  Design and synthesis of isatin/triazole conjugates that induce apoptosis and inhibit migration of MGC-803 cells

  摘要：

  A series of new isatin/triazole conjugates were designed based on the hypothesis that the ester-linked compounds could be enzymatically hydrolyzed by cellular esterases inside the cells. These compounds showed moderate to good growth inhibition toward the tested cancer cells, exerted selective inhibition toward MGC-803 cells and were less toxic to normal cells HL-7702 and GES-1. Of these compounds, compound 5a showed the best inhibitory activity against MGC-803 cells (IC50 = 9.78 mu M), induced apoptosis through multiple mechanisms, as well as inhibited migration of MGC-803 cells. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.08.065

文献信息

• Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches
  作者：Doohyun Lee、Daehun Kim、Seungyeon Lee、Taegeum Kim、Joobin Kim、Sohee Kim、Kwang-Hyeon Liu、Sangkyu Lee、Jong-Sup Bae、Kyung-Sik Song、Chang-Woo Cho、Youn Son、Dong Baek、Taeho Lee

  DOI：10.3390/molecules201119673

  日期：——

  with secondary amines and chloro-acid chlorides; SN2 reaction with sodium azide; and the selective [3 + 2] Hüisgen cycloaddition with appropriate terminal alkynes. The target secondary and tertiary 1,2,3-triazoloamide derivatives were obtained with three-diversity points in excellent overall yields and purities using the reported solid- and solution-phase synthetic routes, respectively.

  开发了用于制备仲和叔1,2,3-三唑酰胺衍生物的有效合成途径。通过先前开发的固相合成方法构建并扩展了第二个α-1,2,3-三唑酰胺库，并通过并行溶液相合成方法构建了叔1,2,3-三唑酰胺库。合成途径依赖于与仲胺和氯酰氯形成酰胺。SN2与叠氮化钠反应；以及使用适当的末端炔烃进行的选择性[3 + 2]Hüisgen环加成反应。使用所报道的固相和溶液相合成路线，分别以优异的总收率和纯度获得具有三个多样性点的目标1,2,3-三唑酰胺二级和三级衍生物。
• Amine-mediated synthesis of amides from 1,3-dicarbonyl compounds through a domino diazo transfer/aminolysis process
  作者：Taíssa A. Costin、Luiz G. Dutra、Adailton J. Bortoluzzi、Marcus M. Sá

  DOI：10.1016/j.tet.2017.06.013

  日期：2017.8

  compound and the nucleophilicity of the amine, the resulting α-diazo-β-keto ester undergoes cleavage of the acyl group to give amides. A multifunctionalized γ-azido-α-diazo-β-keto ester was cleanly prepared in good yields by this one-pot protocol under practical and safe conditions, being employed in a Knoevenagel-type condensation with aromatic aldehydes to give densely functionalized diazo azido compounds

  本文描述了胺作为由1，3-二羰基化合物合成重氮化合物或羧酰胺的催化剂和底物的双重作用。在合适的重氮转移剂的存在下，伯和环状仲胺充当重氮向丙二酸酯，β-酮酸酯和β-二酮的重氮转移反应的碱性催化剂。取决于1，3-二羰基化合物的结构和胺的亲核性，所得的α-重氮-β-酮酯经历酰基的裂解以得到酰胺。多功能γ-叠氮基-α-重氮-β在实际和安全的条件下，通过这一一锅操作规程，以高收率干净地制备了β-酮酯，将其用于与芳香族醛的Knoevenagel型缩合反应中，得到致密的官能化重氮叠氮基化合物。用伯胺进一步处理这些不饱和的γ-叠氮基-α-重氮-β-酮酯很容易就能以高收率得到相应的α-叠氮酰胺，它们被用于铑催化的分子内合成新型吲哚-2-羧酰胺。 C H插入。
• Synthesis of Isocryptolepine‐Triazole Adducts and Evaluation of Their Cytotoxic Activity
  作者：Warabhorn Rodphon、Pavitra Laohapaisan、Nantamon Supantanapong、Onrapak Reamtong、Lukana Ngiwsara、Kriengsak Lirdprapamongkol、Charnsak Thongsornkleeb、Nisachon Khunnawutmanotham、Jumreang Tummatorn、Jisnuson Svasti、Somsak Ruchirawat

  DOI：10.1002/cmdc.202100554

  日期：2021.12.14

  isocryptolepine-triazole hybrids were synthesized using azide rearrangement chemistry and click reaction to prepare a diversified structural library. The synthetic compounds were found to improve cytotoxic activities over the parent isocryptolepine against four cancer cell lines. These triazole hybrids also showed different action against cancer compared to the parent compound with low toxicity.

  使用叠氮化物重排化学和点击反应合成了 18 个异隐烯-三唑杂化物，以制备多样化的结构库。发现合成化合物对四种癌细胞系的细胞毒活性优于母体异隐萜。与低毒性的母体化合物相比，这些三唑杂化物还显示出不同的抗癌作用。
• 1,2,3-Triazole derivatives as new cannabinoid CB1 receptor antagonists
  作者：Duen-Ren Hou、Safiul Alam、Ting-Chun Kuan、Mani Ramanathan、Tsung-Pang Lin、Ming-Shiu Hung

  DOI：10.1016/j.bmcl.2008.11.029

  日期：2009.2

  3-triazole derivatives as CB1 receptor antagonists. The design, synthesis and biological evaluation of N1 and N2 substituted 1,2,3-trizoles are described. The N2 substituted, symmetrical 1,2,3-triazoles are more potent ligands than the unsymmetrical analogues. The in vitro activity of these triazoles is further improved by inserting a methylene group between the central core and the carbonyl side chain

  这封信报道了新的1,2,3-三唑衍生物作为CB1受体拮抗剂的新进入。描述了N 1和N 2取代的1,2,3-三唑的设计，合成和生物学评估。所述Ñ 2取代的，对称的1,2,3-三唑是更有效的配体比非对称的类似物。通过在中心核和羰基侧链之间插入一个亚甲基，可以进一步提高这些三唑的体外活性。在该系列中制备的最有效的拮抗剂（IC 50  <20 nM）是含有苄基酰胺的三唑。这些三唑在CB1和CB2受体之间也显示出极好的选择性（CB2的IC 50  > 10μM； CB2 / CB1> 1000）。
• Design and Synthesis of New Aryloxy‐linked Dimeric 1,2,3‐Triazoles<i>via</i>Click Chemistry Approach: Biological Evaluation and Molecular Docking Study
  作者：Tejshri R. Deshmukh、Smita P. Khare、Vagolu S. Krishna、Dharmarajan Sriram、Jaiprakash N. Sangshetti、Omprakash Bhusnure、Vijay M. Khedkar、Bapurao B. Shingate

  DOI：10.1002/jhet.3608

  日期：2019.8

  for more potent new antitubercular agents has prompted to design and synthesize aryloxy‐linked dimeric 1,2,3‐triazoles (4a–j), from azides (2a‐e) and bis(prop‐2‐yn‐1‐yloxy)benzene (3a–b) on 1,3‐dipolar cycloaddition reaction via copper (I)‐catalyzed click chemistry approach with good to better yields. The titled compounds (4a–j) were designed using molecular hybridization approach by assembling various

  对更有效的新型抗结核药的追求促使设计和合成了由叠氮化物（2a-e）和双（prop-2-yn-1基氧基）芳氧基连接的二聚1,2,3-三唑（4a – j）。）苯（3a – b）通过铜（I）催化的点击化学方法在1,3-偶极环加成反应上具有良好或更高的收率。使用分子杂交方法，通过在单个分子框架中组装各种生物活性药效基团片段，设计了标题化合物（4a – j）。所有合成的化合物都经过了体外筛选针对它们各自的菌株的抗结核，抗真菌和抗氧化活性。其中4h和4i具有最高的抗真菌活性，而化合物4h，4i和4j已经显示出对它们各自的菌株有希望的抗结核活性。除此之外，发现大多数合成的化合物是有效的抗真菌剂和抗氧化剂。良好的键合和非键合相互作用网络将这些分子稳定在真菌CYP51的活性位点，这是通过获得的良好对接位姿以及与酶的相关热力学相互作用实现的。还对合成的化合物的吸收，分布，代谢和排泄特性进行了分析。