2-methyl-3-selenocyanato-1H-indole | 1130-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-methyl-3-selenocyanato-1H-indole
• 英文别名: 2-methyl-3-selenocyanato-indole；2-Methyl-3-selenocyanato-indol；2-Methyl-3-selenocyan-indol；(2-methyl-1H-indol-3-yl) selenocyanate
• CAS: 1130-89-8
• 化学式: C₁₀H₈N₂Se
• 分子量: 235.147
• InChiKey: JANNYDMYOCOLOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-3-selenocyanato-1H-indole 在 iron(III) chloride 、 sodium tetrahydroborate 、 sodium 、 甲烷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.67h， 生成 methyl 5-[(2-methyl-1H-indol-3-yl)selanyl]-1H-benzoimidazol-2-ylcarbamate
  参考文献：
  名称：

  Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

  摘要：

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.071
• 作为产物：
  描述：

  2-甲基吲哚 、 triselenium dicyanide 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 2-methyl-3-selenocyanato-1H-indole
  参考文献：
  名称：

  Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

  摘要：

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.071

文献信息

• Facile, regioselective oxidative selenocyanation of <i>N</i>-aryl enaminones under transition-metal-free conditions
  作者：Ganesh Shivayogappa Sorabad、Mahagundappa Rachappa Maddani

  DOI：10.1039/c9nj05845a

  日期：——

  The present selenocyanation is applied for the synthesis of selenocyanated chromones, indoles and anilines in good to excellent yields.

  目前的硒氰化反应用于合成硒氰基的咖啡因、吲哚和苯胺，产率在良好到优异之间。
• A Facile CAN-Mediated Synthesis of Selenocyanates from Arylalkenes and Heteroarenes
  作者：Vijay Nair、Anu Augustine、Tesmol G. George

  DOI：10.1002/1099-0690(200207)2002:14<2363::aid-ejoc2363>3.0.co;2-7

  日期：2002.7

  Selenocyanation of styrenes and indoles mediated by cerium(IV) ammonium nitrate (CAN) afforded the corresponding selenocyanates in moderate to good yields. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  由硝酸铈（IV）铵（CAN）介导的苯乙烯和吲哚的硒氰化以中等至良好的产率提供相应的硒氰酸酯。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates
  作者：Andrey V. Kachanov、Oleg Yu. Slabko、Olga V. Baranova、Evgenia V. Shilova、Vladimir A. Kaminskii

  DOI：10.1016/j.tetlet.2004.04.071

  日期：2004.5

  Triselenium dicyanide is formed by the interaction of malononitrile and selenium dioxide in dimethylsulfoxide or dimethylformamide. Addition of aromatic amines, indoles and some active methylene compounds to this reaction mixture gives the corresponding selenocyanates in one-pot. (C) 2004 Elsevier Ltd. All rights reserved.
• Lead-free Cs₂AgBiBr₆ double perovskite microcrystals for effective visible-light photocatalytic thio/selenocyanation
  作者：Ting Zhong、Haibo Zhu、Yeye Zheng、Gaowen Ren、Xinmei Xie、Qiangwen Fan、Zongbo Xie、Zhang-Gao Le

  DOI：10.1039/d3cc06087j

  日期：2024.4.11

  An efficient lead-free double perovskite Cs₂AgBiBr₆ catalyzed C-3 thio/selenocyanation of indoles under visible-light have been developed, in which the photocatalyst can be recycled at least five times without a substantial decrease in efficiency.
• Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities
  作者：Qi Guan、Chunming Han、Daiying Zuo、Min'an Zhai、Zengqiang Li、Qian Zhang、Yanpeng Zhai、Xuewei Jiang、Kai Bao、Yingliang Wu、Weige Zhang

  DOI：10.1016/j.ejmech.2014.09.071

  日期：2014.11

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.