N-(2-chloroquinolin-3-yl)acetamide | 137470-14-5

• 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
• 英文名称: N-(2-chloroquinolin-3-yl)acetamide
• CAS: 137470-14-5
• 化学式: C₁₁H₉ClN₂O
• 分子量: 220.658
• InChiKey: YUKKKBJIUVALNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-chloroquinolin-3-yl)acetamide 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 生成 3-Methoxy-3H-[1,2,3]triazolo[4,5-b]quinoline
  参考文献：
  名称：

  The 5,6- and 4,5-Benzo Derivatives of 1-Hydroxy-7-azabenzotriazole

  摘要：

  [GRAPHICS]Syntheses of the two benzo derivatives of HOAt are described. Conversion of the two isomers to the corresponding onium-style coupling reagents gave in one case a guandinium species 14 and in the other, presumably as a result of steric factors, a uronium species 15. The two systems are compared as to their effectiveness in peptide coupling processes.

  DOI：

  10.1021/ol016063j
• 作为产物：
  描述：

  2-氯喹啉-3-胺 、 乙酸酐 生成 N-(2-chloroquinolin-3-yl)acetamide
  参考文献：
  名称：

  The 5,6- and 4,5-Benzo Derivatives of 1-Hydroxy-7-azabenzotriazole

  摘要：

  [GRAPHICS]Syntheses of the two benzo derivatives of HOAt are described. Conversion of the two isomers to the corresponding onium-style coupling reagents gave in one case a guandinium species 14 and in the other, presumably as a result of steric factors, a uronium species 15. The two systems are compared as to their effectiveness in peptide coupling processes.

  DOI：

  10.1021/ol016063j

文献信息

• Reactions of 3-Substituted Quinoline 1-Oxides with Acylating Agents
  作者：Yutaka Miura、Sakae Takaku、Yoshiharu Nawata、Masatomo Hamana

  DOI：10.3987/com-91-5788

  日期：——

  Reactions of 3-fluoro- (1a), 3-bromo,- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table). While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxy-quinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.
• Tetrazolylmethyl quinolines: Design, docking studies, synthesis, anticancer and antifungal analyses
  作者：Saba Kauser J. Shaikh、Ravindra R. Kamble、Shilpa M. Somagond、H.C. Devarajegowda、Sheshagiri R. Dixit、Shrinivas D. Joshi

  DOI：10.1016/j.ejmech.2017.01.043

  日期：2017.3

  A new series of 2,5 and 1,5-regioisomers of the tetrazolyl group viz., 3-[(5-benzyl/benzylthio-2H-tetrazol-2- yl) methyl]-2-chloro-6-substituted quinoline 6h-q and 3-[(5-benzyl/benzylthio-1H-tetrazol-1-yl) methyl]-2-chloro-6-substituted quinolines 7h-q were synthesized. Docking studies of all these compounds with DNA as target using PDB: 1AU5 and 453D revealed that the compounds 6h and 6i act as covalent cross linker on the DNA helix of the former and intercalate the latter both with higher C score values. Another set of docking studies in the active pocket of dihydrofolate reductase and N-myristoyl transferase as targets to assess antifungal activity revealed that compounds 6k, 6l, 6p and 7q (with bromo and fluro substituents) showcases different binding modes and hydrogen bonding. Further, the compounds were screened for anticancer activity (primary cytotoxicity) against NCI-60 Human tumor cell line at a single high dose (10(-5) M) concentration assay. Among the tested compounds, 6h has shown 99.28% of GI against Melanoma (SK-MEL-5) and compound 6i has shown 97.56% of GI against Breast Cancer (T-47D). Further, in vitro antifungal assay against A. fumigatus and C. albicans for these compounds 6h-q and 7h-q revealed potential to moderate activities as compared to the standard. (C) 2017 Elsevier Masson SAS. All rights reserved.