6,8-Dibromo-3-([1,2,5]thiadiazolo[3',4':4,5]benzimidazo[1,2-c]quinazolin-7-yl)-2H-chromen-2-one | 1266552-35-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,8-Dibromo-3-([1,2,5]thiadiazolo[3',4':4,5]benzimidazo[1,2-c]quinazolin-7-yl)-2H-chromen-2-one
• 英文别名: 6,8-dibromo-3-(7-thia-1,6,8,11,19-pentazapentacyclo[10.8.0.02,10.05,9.013,18]icosa-2(10),3,5,8,11,13,15,17,19-nonaen-20-yl)chromen-2-one
• CAS: 1266552-35-5
• 化学式: C₂₃H₉Br₂N₅O₂S
• 分子量: 579.231
• InChiKey: FTOSFVLOONHFJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(6,8-dibromo-2-oxo-2H-chromen-3-yl)-4H-benzo[d][1,3]oxazin-4-one 、 2,1,3-苯并噻二唑-4,5-二胺 在 cellulose sulfuric acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 以94%的产率得到6,8-Dibromo-3-([1,2,5]thiadiazolo[3',4':4,5]benzimidazo[1,2-c]quinazolin-7-yl)-2H-chromen-2-one
  参考文献：
  名称：

  3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]-2H-chromene-2-ones as potent antimicrobial agents

  摘要：

  A series of 3-[benzimidazo(1,2-c) quinazolin-5-yl]-2H-chromene-2-one (6a-6f) and 3-[benzothiadiazoleimidazo( 1,2-c) quinazolin-5-yl]-2H-chromene-2-one derivatives (7a-7f) that incorporate a variety of substituents at the 6-and/or 8-positions of the coumarin moieties have been synthesized utilizing cellulose sulfuric acid as an efficient catalyst under both conventional heating and microwave irradiation procedures. These analogs were evaluated for their antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Streptococcus pyogenes (Gram-positive bacteria), Escherichia Coli, Klebsiella pneumonia, Salmonella typhimurium (Gram-negative bacteria), and Aspergillus niger, Candida albicans, and Aspergillus flavus (Fungi). Two analogs, 6c (a 6,8-dichloro analog, MIC[SA] = 2.5 mu g/mL; MIC[ST] = 2.5 mu g/mL) and 7d (a 6,8-dibromo analog, MIC[ST] = 2.5 mu g/mL) were identified as potent antibacterial agents, and two analogs, 6b (a 6-bromo analog, MIC[AF] = 10 mu g/mL) and 6d (a 6,8-dibromo analog, MIC[AF] = 15 mu g/mL; MIC[CA] = 15 mu g/mL), were identified as potent antifungal agents. Based on the MIC data, analogs 6b, 6c, 6d, and 7d were identified as the most potent antimicrobial agents in the series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.082

文献信息

• 3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]-2H-chromene-2-ones as potent antimicrobial agents
  作者：B. Suresh Kuarm、Y. Thirupathi Reddy、J. Venu Madhav、Peter A. Crooks、B. Rajitha

  DOI：10.1016/j.bmcl.2010.10.082

  日期：2011.1

  A series of 3-[benzimidazo(1,2-c) quinazolin-5-yl]-2H-chromene-2-one (6a-6f) and 3-[benzothiadiazoleimidazo( 1,2-c) quinazolin-5-yl]-2H-chromene-2-one derivatives (7a-7f) that incorporate a variety of substituents at the 6-and/or 8-positions of the coumarin moieties have been synthesized utilizing cellulose sulfuric acid as an efficient catalyst under both conventional heating and microwave irradiation procedures. These analogs were evaluated for their antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Streptococcus pyogenes (Gram-positive bacteria), Escherichia Coli, Klebsiella pneumonia, Salmonella typhimurium (Gram-negative bacteria), and Aspergillus niger, Candida albicans, and Aspergillus flavus (Fungi). Two analogs, 6c (a 6,8-dichloro analog, MIC[SA] = 2.5 mu g/mL; MIC[ST] = 2.5 mu g/mL) and 7d (a 6,8-dibromo analog, MIC[ST] = 2.5 mu g/mL) were identified as potent antibacterial agents, and two analogs, 6b (a 6-bromo analog, MIC[AF] = 10 mu g/mL) and 6d (a 6,8-dibromo analog, MIC[AF] = 15 mu g/mL; MIC[CA] = 15 mu g/mL), were identified as potent antifungal agents. Based on the MIC data, analogs 6b, 6c, 6d, and 7d were identified as the most potent antimicrobial agents in the series. (C) 2010 Elsevier Ltd. All rights reserved.