12-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)dodecyl methanesulfonate

• 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-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)dodecyl methanesulfonate
• 英文别名: 12-[4-(3-Hydroxypropyl)triazol-1-yl]dodecyl methanesulfonate；12-[4-(3-hydroxypropyl)triazol-1-yl]dodecyl methanesulfonate
• 化学式: C₁₈H₃₅N₃O₄S
• 分子量: 389.56
• InChiKey: KVQNNNUTTHIKCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)dodecyl methanesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以73%的产率得到3-(1-(12-iodododecyl)-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：

  12-溴-1-十二烷醇 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 12-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)dodecyl 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

• 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.
• 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.