12-azidododecyl methanesulfonate | 1333383-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 12-azidododecyl methanesulfonate
• CAS: 1333383-55-3
• 化学式: C₁₃H₂₇N₃O₃S
• 分子量: 305.442
• InChiKey: CXQJVJONCCTCBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-azidododecyl methanesulfonate 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 79.5h， 生成 1,1-dimethylethyl [12-(3-pyridinylpropoxy)dodecyl]carbamate
  参考文献：
  名称：

  Synthesis and Evaluation of Antimalarial Activity of Oxygenated 3-alkylpyridine Marine Alkaloid Analogues

  摘要：

  A series of new oxygenated analogues of marine 3‐alkylpyridine alkaloids were prepared from 3‐pyridinepropanol in few steps and in good yields. The key step for the synthesis of these compounds was a Williamson etherification under phase‐transfer conditions. All new compounds were evaluated for their antiplasmodial activity and cytotoxicity. A significant reduction in parasitaemia was observed for some of the prepared compounds, and the majority of them exhibited a selectivity index (SI) ranging from 2.78 to 15.58, which suggests that these compounds may be a promising class of substances with antimalarial activity.

  DOI：

  10.1111/j.1747-0285.2011.01154.x
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 12-azidododecyl methanesulfonate
  参考文献：
  名称：

  合成的3-烷基吡啶生物碱类似物作为抗白血病细胞系的新型支架：细胞毒性评估和作用方式

  摘要：

  白血病是一种恶性疾病，起源于骨髓，是血细胞产生的局部区域。化学疗法是提高患者生存率的替代方法之一。在这种情况下，寻找具有潜在细胞毒性作用的新化合物是合理的。本工作评估了16种新的3-烷基吡啶生物碱合成类似物的细胞毒活性。通过MTT体外测定针对THP-1（急性单核细胞白血病），K562（慢性髓细胞性白血病）和PBMC（外周血单核）人细胞确定细胞毒性谱。为了研究其作用机理，细胞周期分析以及TP53，p21，Bax，Bcl2，NOX-1，NOX-2的变化，通过qPCR进行NOX-4和p47-phox基因表达，并测量活性氧（2'，7'-二氯二氢荧光素二乙酸盐和二氢乙啶）。化合物4c，5b，5c和6d对THP-1具有最高的活性和选择性，而化合物7c和11对K562具有更高的活性。所有这些都在测试菌株中诱导了细胞凋亡。关于作用机理的研究，观察到被激活的途径是p53非依赖性途径。这项工作中提供的数据表明

  DOI：

  10.1007/s00044-019-02395-5

文献信息

• Long-chain alkyltriazoles as antitumor agents: synthesis, physicochemical properties, and biological and computational evaluation
  作者：Vanessa Silva Gontijo、Michael Éder Oliveira、Rafael José Resende、Amanda Luisa Fonseca、Renata Rachide Nunes、Moacyr Comar Júnior、Alex Gutterres Taranto、Natalia Machado Pereira Oliveira Torres、Gustavo Henrique Ribeiro Viana、Luciana Maria Silva、Rosemeire Brondi Alves、Fernando Pilla Varotti、Rossimiriam Pereira Freitas

  DOI：10.1007/s00044-014-1137-3

  日期：2015.1

  A series of novel long-chain alkyltriazoles were prepared from commercial diols in a rapid process with good yields. The compounds were evaluated in vitro for their anticancer potential against two human cancer cell lines: colon carcinoma (RKO) and uterine carcinoma (HeLa). The results of colorimetric MTT assays showed that six of fourteen compounds tested decreased cell viability in these cell lines. Compounds 5e and 6a were the most active against RKO cells, with IC50 values of 16.70 and 14.57 mu M, respectively. The same compounds, 5e and 6a, were the most active in HeLa cells as well, with IC50 values of 11.05 and 12.77 mu M, respectively. In addition, compound 5e was found to induce apoptosis in RKO cells, as assessed by TUNEL assay. The results suggest that compound 5e may be a promising prototype anticancer agent.
• Leishmanicidal, antiproteolytic, and mutagenic evaluation of alkyltriazoles and alkylphosphocholines
  作者：Vanessa Silva Gontijo、Patrícia Ferreira Espuri、Rosemeire Brondi Alves、Luiz Fernando de Camargos、Fábio Vieira dos Santos、Wagner Alves de Souza Judice、Marcos José Marques、Rossimiriam Pereira Freitas

  DOI：10.1016/j.ejmech.2015.06.005

  日期：2015.8

  A series of 16 simple long-chain alkyltriazoles and two novel alkylphosphocholine derivatives containing an aside moiety were evaluated in vitro for their leishmanicidal activity against. Among the 18 compounds tested, the eight most active compounds against promastigote forms were selected for further evaluation against amastigote forms. These compounds were also evaluated for their cytotoxicity against murine macrophages and tested as inhibitors of cysteine protease rCPB2.8, an important target for development of antileishmanial drugs. The mutagenicity of some of these compounds was also evaluated in prokaryotic and eukaryotic cells to assess any genetic effects of the leishmanicidal candidates. The compound 4, an alkylphosphocholine derivative, was found to be the most potent against amastigote forms with an IC50 of 3.81 mu M, comparable to that of pentamidine (IC50 = 6.62 mu M) and amphotericin B (IC50 = 6.10 mu M), two established leishmanicidal drugs. Compound 4 also exhibited the best selectivity index (SI) values of the series, demonstrating low toxicity against macrophages and a cLogP value higher than 5. Among the alkyltriazoles,, compounds 13 and 14 were the most active against promastigote and amastigote forms. They were then evaluated for their mutagenicity in vitro; the mutagenicity index (MI) values were lower than 2, suggesting that these compounds are not mutagenic. (C) 2015 Elsevier Masson SAS. All rights reserved.
• In vivo evaluation of anti-Leishmania activity of alkyltriazoles and alkylphosphocholines by oral route
  作者：Vanessa Silva Gontijo、Fabio Antônio Colombo、Patrícia Ferreira Espuri、Poliany Graziella de Freitas、Juliana Barbosa Nunes、Levy Bueno Alves、Márcia Paranho Veloso、Rosemeire Brondi Alves、Rossimiriam Pereira Freitas、Marcos José Marques

  DOI：10.1016/j.exppara.2021.108123

  日期：2021.7
• Design, synthesis, and biodistribution studies of new analogues of marine alkaloids: Potent in vitro and in vivo fungicidal agents against Candida spp.
  作者：Jéssica Tauany Andrade、William Gustavo Lima、Jaqueline França Sousa、Aline Aparecida Saldanha、Nívea Pereira De Sá、Fernanda Barbara Morais、Mayra Karla Prates Silva、Gustavo Henrique Ribeiro Viana、Susana Johann、Adriana Cristina Soares、Leonardo Allan Araújo、Simone Odília Antunes Fernandes、Valbert Nascimento Cardoso、Jaqueline Maria Siqueira Ferreira

  DOI：10.1016/j.ejmech.2020.113048

  日期：2021.1