9-azidononyl methanesulfonate | 1333383-54-2

• 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: 9-azidononyl methanesulfonate
• CAS: 1333383-54-2
• 化学式: C₁₀H₂₁N₃O₃S
• 分子量: 263.361
• InChiKey: KCUNTTMKWYPNSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  11
• 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：

  9-azidononyl methanesulfonate 在 potassium fluoride 、 copper(ll) sulfate pentahydrate 、 18-冠醚-6 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 3-(1-(9-fluorononyl)-1H-1,2,3-triazol-4-yl)propan-1-ol
  参考文献：
  名称：

  Long-chain alkyltriazoles as antitumor agents: synthesis, physicochemical properties, and biological and computational evaluation

  摘要：

  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.

  DOI：

  10.1007/s00044-014-1137-3
• 作为产物：
  描述：

  9-溴-1-壬醇 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 9-azidononyl methanesulfonate
  参考文献：
  名称：

  Leishmanicidal, antiproteolytic, and mutagenic evaluation of alkyltriazoles and alkylphosphocholines

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.06.005

文献信息

• Effect of 3-Alkylpyridine Marine Alkaloid Analogues in<i>Leishmania</i>Species Related to American Cutaneous Leishmaniasis
  作者：Patrícia A. Machado、Flaviane F. Hilário、Lidiane O. Carvalho、Mariana L. T. Silveira、Rosemeire B. Alves、Rossimiriam P. Freitas、Elaine S. Coimbra

  DOI：10.1111/cbdd.12017

  日期：2012.11

  A series of oxygenated analogues of marine 3‐alkylpyridine alkaloids were synthesized, and their leishmanicidal activity was assayed. All compounds were prepared from 3‐pyridinepropanol in few steps and in good yields. The key step for the synthesis of these compounds was a classic Williamson etherification under phase‐transfer conditions. Besides toxicity in peritoneal macrophages, the compounds exhibited

  合成了一系列海洋3-烷基吡啶生物碱的氧化类似物，并测定了其杀螨活性。所有化合物均由3-吡啶丙醇以少量步骤制备，并且收率很高。合成这些化合物的关键步骤是在相转移条件下进行经典的Williamson醚化反应。除了对腹膜巨噬细胞有毒性外，这些化合物还显示出显着的杀螨活性。在测试的十二种化合物中，五种化合物对亚马逊利什曼原虫和巴西利什曼原虫的前鞭毛体形式具有很强的杀螨活性，IC 50低于10μm。化合物11，14，15，和16显示对细胞内无鞭毛体强烈leishmanicidal活性（IC 50个的值2.78; 0.27; 1.03和1.33μ米，分别地），可以由于一氧化氮产生的巨噬细胞的激活这是不可能的。
• Synthesis and Evaluation of Antimalarial Activity of Oxygenated 3-alkylpyridine Marine Alkaloid Analogues
  作者：Flaviane F. Hilário、Renata Cristina de Paula、Mariana L. T. Silveira、Gustavo H. R. Viana、Rosemeire B. Alves、Juliana R. C. S. Pereira、Luciana Maria Silva、Rossimiriam P. de Freitas、Fernando de Pilla Varotti

  DOI：10.1111/j.1747-0285.2011.01154.x

  日期：2011.9

  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.