5-methyl-8-nitro-[1,2,4]triazino[5,6-b]indole-3-thiol

• 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: 5-methyl-8-nitro-[1,2,4]triazino[5,6-b]indole-3-thiol
• 化学式: C₁₀H₇N₅O₂S
• 分子量: 261.264
• InChiKey: GFRKRVMUITWERR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-8-nitro-[1,2,4]triazino[5,6-b]indole-3-thiol 、 4-nitro-3-phenylfuroxan 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以76%的产率得到5-methyl-8-nitro-3-[(5-oxido-4-phenyl-1,2,5-oxadiazol-3-yl)sulfanyl]-5-[1,2,4]triazino[5,6-b]indole
  参考文献：
  名称：

  亲核取代硝基呋喃烷中的硝基被杂环硫醇和羟基衍生物合成，从而合成杂芳基硫烷基和杂芳氧基呋喃*

  摘要：

  我们报告了一种合成方法，该方法基于4-呋喃呋喃中的硝基被HetS和HetO基团通过与杂芳硫醇和羟基的反应引入的亲核取代，合成了包含呋喃和S-和О-桥连接的杂环片段的未知未知杂环系统1,8-二氮杂双环[5.4.0] undec-7-ene /МеCN系统中的室温杂环。我们表明，杂芳硫醇与在环С-3原子上包含脂肪族，苄基和芳族取代基的4-硝基呋喃喃反应，从而获得了以前未知的杂芳基硫烷基呋喃烷的文库，而仅在4-情况下与羟基杂环的反应才成功硝基-3-苯基呋喃喃，其余的硝基呋喃烷显示低的反应性，并且仅在某些情况下可以获得取代产物。2，CONH 2）起氧化剂作用，形成1,2-二（杂芳基）二硫化物。

  DOI：

  10.1007/s10593-015-1678-5
• 作为产物：
  描述：

  5-硝基靛红 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-methyl-8-nitro-[1,2,4]triazino[5,6-b]indole-3-thiol
  参考文献：
  名称：

  Triazino indole–quinoline hybrid: A novel approach to antileishmanial agents

  摘要：

  A novel series of 1,2,4-triazino-[5,6b] indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 mu M and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 mu M, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 mu M, SI >= 7). (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.11.018

文献信息

• Triazino indole–quinoline hybrid: A novel approach to antileishmanial agents
  作者：Rashmi Sharma、Anand Kumar Pandey、Rahul Shivahare、Khushboo Srivastava、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2013.11.018

  日期：2014.1

  A novel series of 1,2,4-triazino-[5,6b] indole-3-thione covalently linked to 7-chloro-4-aminoquinoline have been synthesized and evaluated for their in vitro activity against extracellular promastigote and intracellular amastigote form of Leishmania donovani. Among all tested compounds, compounds 7a and 7b were found to be the most active with IC50 values 1.11, 0.36 mu M and selectivity index (SI) values 67, >1111, respectively, against amastigote form of L. donovani which is several folds more potent than the standard drugs, miltefosine (IC50 = 8.10 mu M, SI = 7) and sodium stibo-gluconate (IC50 = 54.60 mu M, SI >= 7). (C) 2013 Published by Elsevier Ltd.
• Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives*
  作者：Leonid L. Fershtat、Margarita A. Epishina、Alexander S. Kulikov、Marina I. Struchkova、Nina N. Makhova

  DOI：10.1007/s10593-015-1678-5

  日期：2015.2

  aromatic substituents at the ring С-3 atom, allowing to obtain a library of previously unknown hetarylsulfanylfuroxans, while the reaction with hydroxy heterocycles was successful only in the case of 4-nitro-3-phenylfuroxan, the rest of the nitrofuroxans showing low reactivity, and substitution products could be obtained only in certain cases. 4-Nitrofuroxans with electron-withdrawing substituents (NO2

  我们报告了一种合成方法，该方法基于4-呋喃呋喃中的硝基被HetS和HetO基团通过与杂芳硫醇和羟基的反应引入的亲核取代，合成了包含呋喃和S-和О-桥连接的杂环片段的未知未知杂环系统1,8-二氮杂双环[5.4.0] undec-7-ene /МеCN系统中的室温杂环。我们表明，杂芳硫醇与在环С-3原子上包含脂肪族，苄基和芳族取代基的4-硝基呋喃喃反应，从而获得了以前未知的杂芳基硫烷基呋喃烷的文库，而仅在4-情况下与羟基杂环的反应才成功硝基-3-苯基呋喃喃，其余的硝基呋喃烷显示低的反应性，并且仅在某些情况下可以获得取代产物。2，CONH 2）起氧化剂作用，形成1,2-二（杂芳基）二硫化物。