(1-dodecyl-1H-1,2,3-triazol-4-yl)methanol | 1281308-61-9

• 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-dodecyl-1H-1,2,3-triazol-4-yl)methanol
• 英文别名: (1-Dodecyltriazol-4-yl)methanol
• CAS: 1281308-61-9
• 化学式: C₁₅H₂₉N₃O
• 分子量: 267.415
• InChiKey: LQBMXOSQLXFIDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-dodecyl-1H-1,2,3-triazol-4-yl)methanol 在 Jones reagent 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 4.5h， 生成 (E)-2-(4-benzylpiperidin-1-yl)-N-(4-(3-(1-dodecyl-1H-1,2,3-triazol-4-yl)acryloyl)phenyl)acetamide
  参考文献：
  名称：

  新型1,2,3-三唑系链查尔酮乙酰胺衍生物的合成和抗增殖活性。

  摘要：

  以优异的产率合成了一系列新的1,2,3-三唑系链查尔酮乙酰胺衍生物（7a-c和8a-r），并通过分析和光谱（FT-IR，1 H NMR，13 C）确定了其结构NMR和HRMS）研究。评价了新合成的衍生物对四种人类癌细胞系的细胞毒活性，所述四种人类癌细胞系诸如HeLa（人类宫颈癌），A549（人类肺泡腺癌），MCF-7（人类乳腺腺癌）和SKNSH（人类脑癌）。其中，化合物7c对HeLa（IC 50 7.41 + 0.8μM），SKNSH（IC 50 8.68 + 1.1μM ），MCF-7（IC 50）具有良好的抗增殖活性与标准药物阿霉素相比，化合物7a和7b分别具有IC 50 7.95–11.62μM的抗人增殖能力，而化合物7a和7b分别对上述四种人类癌细胞系的抗增殖性有希望，其IC 50为7.95-11.62μM。我们探索了HDAC8（PDB ID：3SFH）和EHMT2（PDB ID：

  DOI：

  10.1016/j.bmcl.2020.127304
• 作为产物：
  描述：

  2-丙炔-1-醇 、 溴代十二烷 在 sodium azide 、 LaCu_0.7Mn_0.3O₃ 作用下， 以 水 为溶剂， 以90%的产率得到(1-dodecyl-1H-1,2,3-triazol-4-yl)methanol
  参考文献：
  名称：

  通过 LaCuxMn1-xO3 纳米粒子声催化的点击反应合成带有有机硅-硫基团的新型 1,4-二取代 1,2,3-三唑

  摘要：

  摘要 开发了一种高效、环保的一锅法，用于在 LaCuxMn1-xO3 钙钛矿氧化物上通过苄基卤化物、末端炔烃和叠氮化钠的 1,3-偶极环加成反应合成 1,2,3-三唑。发现 LaCu0.7Mn0.3O3 在水介质中超声辐照下具有低催化剂负载量的活性。在没有任何添加剂或碱的情况下，在纳米催化剂的存在下，反应有效地进行，反应时间显着减少。催化剂可以循环使用至少5次，对反应结果没有任何显着影响。此外，使用二硫化碳和三（三甲基甲硅烷基）甲基锂合成了一系列新型有机硅硫取代的 1,2,3-三唑衍生物。图形概要

  DOI：

  10.1080/00397911.2016.1217339

文献信息

• A versatile solvent-free azide–alkyne click reaction catalyzed by in situ generated copper nanoparticles
  作者：Atchutarao Pathigoolla、Ramachandra P. Pola、Kana M. Sureshan

  DOI：10.1016/j.apcata.2012.12.025

  日期：2013.2

  A general, high-yielding and efficient methodology for the copper catalyzed azide–alkyne cycloaddition (CuAAC) reaction catalyzed by in situ generated copper nanoparticles (CuNPs) or their clusters is reported. This simple reaction is facile in water, organic solvents and solvent-free conditions under ambient, open-air conditions and requires no special reaction conditions and chromatographic separation

  报告了一种由原位生成的铜纳米粒子（CuNPs）或其簇催化的铜催化的叠氮化物-炔烃环加成反应（CuAAC）的通用，高产且高效的方法。这种简单的反应易于在环境，露天条件下的水，有机溶剂和无溶剂条件下进行，并且不需要特殊的反应条件和色谱分离。
• Functionalized 1,2,3-triazolium salts as potential agents against visceral leishmaniasis
  作者：Ayla das Chagas Almeida、Raíssa Soares Meinel、Yasmim Lopes Leal、Thiago P. Silva、Nícolas Glanzmann、Débora Vasconcelos Costa Mendonça、Luísa Perin、Edézio Ferreira Cunha-Júnior、Eduardo A. F. Coelho、Rossana C. N. Melo、Adilson David da Silva、Elaine Soares Coimbra

  DOI：10.1007/s00436-022-07431-9

  日期：2022.5

  new antileishmanial compounds. Here, we reported the synthesis of seven new acetyl functionalized 1,2,3-triazolium salts, together with four 1,2,3-triazole precursors, and investigated their effect against different strains of L. infantum from dogs and humans. The 1,2,3-triazolium salts exhibited better activity than the 1,2,3-triazole derivatives with IC50 range from 0.12 to 8.66 μM and, among them

  内脏利什曼病 (VL) 是最严重的利什曼病临床形式，如果不治疗会致命。为了寻找更有效的 VL 治疗方法，主要策略之一是开发和筛选新的抗寄生虫化合物。在这里，我们报告了七种新的乙酰功能化 1,2,3-三唑盐以及四种 1,2,3-三唑前体的合成，并研究了它们对来自狗和人类的不同菌株婴儿乳杆菌的影响。1,2,3-三唑鎓盐的活性优于 1,2,3-三唑衍生物，IC 50范围为 0.12 至 8.66 μM，其中化合物5对前鞭毛体表现出显着的活性（IC 50为 4.55 至 5.28 μM）和细胞内无鞭毛体（IC50从 5.36 到 7.92 μM），具有最佳的选择性指数（SI ~ 6-9）并降低了毒性。我们使用生化和超微结构方法的研究结果表明，化合物5靶向L. infantum前鞭毛体的线粒体，导致活性氧 (ROS) 的形成、线粒体膜电位的增加和线粒体的改变。此外，定量透射电子显微镜 (TEM) 显
• Novel functionalized 1,2,3-triazole derivatives exhibit antileishmanial activity, increase in total and mitochondrial-ROS and depolarization of mitochondrial membrane potential of Leishmania amazonensis
  作者：Raíssa Soares Meinel、Ayla das Chagas Almeida、Pedro Henrique Fazza Stroppa、Nícolas Glanzmann、Elaine Soares Coimbra、Adilson David da Silva

  DOI：10.1016/j.cbi.2019.108850

  日期：2020.1

  1,2,3-triazolium salts are poorly understood regarding their antileishmanial activity. Hence, as an effort to identify novel chemical scaffolds as antileishmanial agents, a series of 1,2,3-triazolium salts (TS) and corresponding 1,2,3-triazole (T) precursors including new epoxide derivatives were synthesized and assayed against Leishmania amazonensis promastigote and intracellular amastigote forms. Among them, the compound TS-6 exhibited promising activity on promastigotes (IC50 = 3.61 mu M) and intracellular amastigotes (IC50 = 7.61 mu M) of L. amazonensis, superior to miltefosine (IC50 > 10.0 mu M), used as reference drug. In addition, TS-6 showed negligible cytotoxicity on murine peritoneal macrophages with a SI of about 10. Studies on the mode of action of TS-6 indicate mitochondrial dysfunction through an increase in 'total' and mitochondrial-ROS as well as depolarization of mitochondrial membrane potential of L. amazonensis promastigotes. In silico physicochemical studies indicate that the TS-6 could potentially be used as an oral drug.
• Correlation of structural features of novel 1,2,3-triazoles with their neurotoxic and tumoricidal properties
  作者：Elaine Maria de Souza-Fagundes、Johannes Delp、PedroH.D.M. Prazeres、Lucas Bonfim Marques、Arturene Maria Lino Carmo、Pedro Henrique Fazza Stroppa、Nicolas Glanzmann、Jaffar Kisitu、Dàvid Szamosvàri、Thomas Böttcher、Marcel Leist、Adilson David da Silva

  DOI：10.1016/j.cbi.2018.06.029

  日期：2018.8

  Triazoles are interesting templates for novel chemotherapeutic drugs. We synthesized here 17 1,3,4-substituted-1,2,3-triazoles that differed in their l'-substituent (variable alkyl chain lengths C3-C12), the 3'-substituent (no substituent, -methyl or -propyl) or the salt form obtained. Several of the compounds were cytotoxic (mu M range) for tumor cells (HL-60, Jurkat, MCF-7, HCT-116), and when the effect was compared to non-transformed cells (Vero), selectivity ratios of up to 23-fold were obtained. To estimate the liability of these potential drug candidates for triggering neurotoxicity, we used the LUHMES cell-based NeuriTox assay. This test quantifies damage to the neurites of human neurons. The four most potent tumoricidal compounds were found to be neurotoxic in a concentration range similar to the one showing tumor cell toxicity. As the neurites of the LUHMES neurons were affected at > 4-fold lower concentrations than the overall cell viability, the novel triazoles were classified as specific neurotoxicants. The structure-activity relationship (SAR) for neurotoxicity was sharply defined and correlated with the one for anti-neoplastic activity. Based on this SAR, two non-neurotoxic compounds were predicted, and testing in the NeuriTox assay confirmed this prediction. In summary, the panel of novel triazoles generated and characterized here, allowed to define structural features associated with cytotoxicity and neurotoxicity. Moreover, the study shows that potential neurotoxic side effects may be predicted early in drug development if highly sensitive test methods for neurite integrity are applied.