(R)-6-((1-methyl-1H-indol-3-yl)methyl)-2,3-diphenyl-5,6-dihydroimidazo[2,1-b]thiazole

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-6-((1-methyl-1H-indol-3-yl)methyl)-2,3-diphenyl-5,6-dihydroimidazo[2,1-b]thiazole
• 英文别名: (6R)-6-[(1-methylindol-3-yl)methyl]-2,3-diphenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole
• 化学式: C₂₇H₂₃N₃S
• 分子量: 421.566
• InChiKey: IWNAFTRZAZMNHY-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 2-溴-2-苯基乙酰苯 以 乙醇 为溶剂， 反应 0.17h， 生成 (R)-6-((1-methyl-1H-indol-3-yl)methyl)-2,3-diphenyl-5,6-dihydroimidazo[2,1-b]thiazole
  参考文献：
  名称：

  Identification of 5,6-dihydroimidazo[2,1- b ]thiazoles as a new class of antimicrobial agents

  摘要：

  In an effort to develop novel antimicrobial agents against drug-resistant bacterial infections, 5,6-dihydroimidazo[2,1-b]thiazole compounds were synthesized and tested for their antimicrobial activity. Eight compounds comprised by two sub-scaffolds were identified as hits against methicillin-resistant Staphylococcus aureus (MRSA). These hits were modified at 6-position by replacing (S)-6 to (R)-6 configuration and the (R)-isomers increased their antimicrobial activities by two-fold. The most active compound showed a MIC90 value of 3.7 mu g/mL against MRSA in a standard microdilution bacterial growth inhibitory assay. This compound protected wax moth worms against MRSA at a dose of 5x MIC using a worm infectious model. This compound also exhibited inhibition of DNA gyrase activity in a DNA gyrase supercoil assay, suggesting the 5,6-dihydroimidazo[2,1-b]thiazoles may target DNA gyrase for the antimicrobial action. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.027

文献信息

• Identification of 5,6-dihydroimidazo[2,1- b ]thiazoles as a new class of antimicrobial agents
  作者：Yangmei Li、Nina Bionda、Renee Fleeman、Hongjie Wang、Akihiko Ozawa、Richard A. Houghten、Lindsey Shaw

  DOI：10.1016/j.bmc.2016.09.027

  日期：2016.11

  In an effort to develop novel antimicrobial agents against drug-resistant bacterial infections, 5,6-dihydroimidazo[2,1-b]thiazole compounds were synthesized and tested for their antimicrobial activity. Eight compounds comprised by two sub-scaffolds were identified as hits against methicillin-resistant Staphylococcus aureus (MRSA). These hits were modified at 6-position by replacing (S)-6 to (R)-6 configuration and the (R)-isomers increased their antimicrobial activities by two-fold. The most active compound showed a MIC90 value of 3.7 mu g/mL against MRSA in a standard microdilution bacterial growth inhibitory assay. This compound protected wax moth worms against MRSA at a dose of 5x MIC using a worm infectious model. This compound also exhibited inhibition of DNA gyrase activity in a DNA gyrase supercoil assay, suggesting the 5,6-dihydroimidazo[2,1-b]thiazoles may target DNA gyrase for the antimicrobial action. (C) 2016 Elsevier Ltd. All rights reserved.