2,9-diphenyl-2,3-dihydrothieno[3,2-b]quinoline | 17517-73-6

• 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: 2,9-diphenyl-2,3-dihydrothieno[3,2-b]quinoline
• 英文别名: 2,9-diphenyl-2,3-dihydro-thieno[3,2-b]quinoline；2,9-Diphenyl-2,3-dihydro-thieno<3,2-b>chinolin；2,9-Diphenyl-2,3-dihydrothieno[3,2-b]quinoline
• CAS: 17517-73-6
• 化学式: C₂₃H₁₇NS
• 分子量: 339.461
• InChiKey: WBWGEKQEVQHBGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,5-dihydro-5-phenyl-3(2H)-thiophenone 、 2-氨基二苯甲酮 在 三氟乙酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 20.0~100.0 ℃ 、100.0 kPa 条件下， 反应 0.5h， 以98%的产率得到2,9-diphenyl-2,3-dihydrothieno[3,2-b]quinoline
  参考文献：
  名称：

  A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines

  摘要：

  A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedlander annulation of 5-aryldihydro-3(2H)-thiophenones and 2-aminobenzophenones in the presence of trifluoroacetic acid in good yields under microwave irradiation at 100 degrees C. The 2,9-diatyl-2,3-dihydrothieno[3,2-b]quinolines were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the 17 compounds screened, 7-chloro-2-(2,4-dichlorophenyl)-9-phenyl-2,3-dihydrothieno-[3,2-b]quinoline and 7-chloro-2-(3-nitrophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline display maximum activity with MIC of 0.90 and 0.95 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. Ail rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.011

文献信息

• Furo-, Pyrano- und Oxepino-chinoline sowie deren Schwefel-Analoga
  作者：G. Kempter、P. Zänker、H.-D. Zürner

  DOI：10.1002/ardp.19673001005

  日期：——

  Aus aromatischen o‐Amino‐ketonen und heterocyclischen Ringketonen, die in 3‐ bzw. 4‐Stellung zur Carbonylgruppe Sauerstoff bzw. Schwefel enthalten, werden heterocyclisch b‐kondensierte Chinoline hergestellt.

  由芳香族邻氨基酮和杂环酮（其 3 位或 4 位含有氧和硫）到羰基，生成杂环 b-稠合喹啉。
• A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines
  作者：Kamaraj Balamurugan、Veerappan Jeyachandran、Subbu Perumal、Thimmappa H. Manjashetty、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.11.011

  日期：2010.2

  A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedlander annulation of 5-aryldihydro-3(2H)-thiophenones and 2-aminobenzophenones in the presence of trifluoroacetic acid in good yields under microwave irradiation at 100 degrees C. The 2,9-diatyl-2,3-dihydrothieno[3,2-b]quinolines were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the 17 compounds screened, 7-chloro-2-(2,4-dichlorophenyl)-9-phenyl-2,3-dihydrothieno-[3,2-b]quinoline and 7-chloro-2-(3-nitrophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline display maximum activity with MIC of 0.90 and 0.95 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. Ail rights reserved.