4-叠氮基-6-甲氧基-2-甲基喹啉 | 149848-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4-叠氮基-6-甲氧基-2-甲基喹啉
• 英文名称: 4-azido-6-methoxy-2-methylquinoline
• 英文别名: 4-Azido-6-methoxy-2-methyl-chinolin
• CAS: 149848-18-0
• 化学式: C₁₁H₁₀N₄O
• 分子量: 214.227
• InChiKey: WRMIMIPYKZLMST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-叠氮基-6-甲氧基-2-甲基喹啉 在 palladium 10% on activated carbon 、 氢气 、 碘 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 80.0 ℃ 、294.21 kPa 条件下， 反应 28.0h， 生成 2-(5-diethylaminomethyl-2-oxo-oxazolidin-3-yl)-N-(6-methoxy-2-methylquinolin-4-yl)acetamide
  参考文献：
  名称：

  Design, synthesis and docking studies of quinoline-oxazolidinone hybrid molecules and their antitubercular properties

  摘要：

  New series of quinoline-oxazolidinone hybrid molecules were synthesized based on the preliminary docking studies. All the newly synthesized compounds were characterized by spectral analyses. The newly synthesized compounds were screened for their antimycobacterial properties based on the promising preliminary antibacterial screening results. Amongst tested compounds, compounds 8a, 8j and 13a were active at 0.65 mu g/mL against Mycobacterium tuberculosis H(37)Rv strain. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands 8a, 8j and 13a. These compounds exhibited well established bonds with one or more amino acids in the receptor active pocket. From the docking studies, compound 8j was considered to be the best inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.049
• 作为产物：
  描述：

  4-肼基-6-甲氧基-2-甲基喹啉 在 盐酸 、 sodium nitrite 作用下， 生成 4-叠氮基-6-甲氧基-2-甲基喹啉
  参考文献：
  名称：

  Savini; Massarelli; Pellerano, Il Farmaco, 1993, vol. 48, # 4, p. 515 - 528

  摘要：

  DOI：

文献信息

• Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety
  作者：K.D. Thomas、Airody Vasudeva Adhikari、N. Suchetha Shetty

  DOI：10.1016/j.ejmech.2010.05.030

  日期：2010.9

  A new series of [1-(6-methoxy-2-methylquinolin-4-y1)-1H-1,2,3-triazol-4-yl] methanamine derivatives were synthesized starting from 4-methoxyaniline through multi-step reactions. The title compounds 5a-y were prepared by treating the azide intermediate 4 with propargyl bromide and different alkyl/heterocyclic amines in a sequential three component synthesis. All the new compounds were characterized by spectral and elemental analyses. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against pathogenic strains. The preliminary screening results indicated that most of the compounds demonstrated moderate to very good antibacterial and antifungal activities, comparable to the first-line drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.
• New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents
  作者：K.D. Thomas、Airody Vasudeva Adhikari、Imran H. Chowdhury、E. Sumesh、Nishith K. Pal

  DOI：10.1016/j.ejmech.2011.03.039

  日期：2011.6

  Three new series of quinoline-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines were synthesized through multi-step reactions. The required intermediate, [1-(6-methoxy-2-methylquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methanol (2) was prepared by treating 4-azido-6-methoxy-2-methylquinoline (1) with propargyl alcohol. Three different series of compounds were synthesized from this intermediate. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 2 was confirmed by X-ray crystallographic study. Further, the title compounds were evaluated for their in vitro anti-bacterial activity against five different bacterial strains and anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv. Mycobacterium smegmatis (ATCC 19420) and Mycobacterium fortuitum (ATCC 19542). Title compounds, 6a, 6d, 6i, 6j, 7e, 10a and 10i were found to be active against Mycobacterium tuberculosis H37Rv strain and could be lead molecules of interest. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Koenigs; v. Loesch, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 143, p. 59,62
  作者：Koenigs、v. Loesch

  DOI：——

  日期：——
• Savini; Massarelli; Corti, Il Farmaco, 1994, vol. 49, # 5, p. 363 - 369
  作者：Savini、Massarelli、Corti、Chiasserini、Pellerano、Bruni

  DOI：——

  日期：——