(S)-6-isobutyl-3-(naphthalen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole | 1266766-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-6-isobutyl-3-(naphthalen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole
• 英文别名: (6S)-6-(2-methylpropyl)-3-naphthalen-2-yl-5,6-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 1266766-60-2
• 化学式: C₁₉H₂₀N₂S
• 分子量: 308.447
• InChiKey: QUUJUAIYKAVETI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-6-isobutyl-3-(naphthalen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole 在 氢氟酸 作用下， 反应 1.5h， 以63%的产率得到(6S)-6-methyl-2,3-diphenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  2,3,6-三取代-5,6-二氢咪唑并[2,1-b]噻唑衍生物的高通量合成

  摘要：

  报道了一种简便的合成 2,3,6-三取代-5,6-二氢咪唑并[2,1- b ]噻唑的方法。通过用1,1'-硫代羰基二咪唑处理树脂结合的二胺形成树脂结合的环状硫脲，然后与α-卤代酮反应生成树脂结合的异硫脲。树脂结合异硫脲的 HF 处理导致产物裂解并同时形成烯胺键。这导致以高产率和纯度形成2,3,6-三取代-5,6-二氢咪唑并[2,1- b ]噻唑。

  DOI：

  10.1016/j.tetlet.2010.12.006
• 作为产物：
  描述：

  、 2-溴代-2-乙酰基萘 以 乙醇 为溶剂， 反应 0.17h， 生成 (S)-6-isobutyl-3-(naphthalen-2-yl)-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

• High throughput synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole derivatives
  作者：Yangmei Li、Marc Giulianotti、Richard A. Houghten

  DOI：10.1016/j.tetlet.2010.12.006

  日期：2011.2

  A facile approach to the synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole was reported. A resin bound cyclic thiourea was formed by the treatment of a resin bound diamine with 1,1′-thiocarbonyldiimidazole, and then reacted with a α-haloketone to generate a resin bound isothiourea. HF treatment of the resin bound isothiourea resulted in the cleavage of the product and simultaneous

  报道了一种简便的合成 2,3,6-三取代-5,6-二氢咪唑并[2,1- b ]噻唑的方法。通过用1,1'-硫代羰基二咪唑处理树脂结合的二胺形成树脂结合的环状硫脲，然后与α-卤代酮反应生成树脂结合的异硫脲。树脂结合异硫脲的 HF 处理导致产物裂解并同时形成烯胺键。这导致以高产率和纯度形成2,3,6-三取代-5,6-二氢咪唑并[2,1- b ]噻唑。
• 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.