3,4-di-p-tolyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole | 97059-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-di-p-tolyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole
• 英文别名: 5,6-di-p-tolyl-2,3-dihydro-imidazo[2,1-b]thiazole；5,6-Bis(4-methylphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 97059-60-4
• 化学式: C₁₉H₁₈N₂S
• 分子量: 306.431
• InChiKey: VYTZMHFDDIDIBA-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C
• 沸点：
  485.3±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-2-氯乙烷 、 4,5-二对甲苯-1,3-二氢咪唑-2-硫酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以49%的产率得到3,4-di-p-tolyl-6,7-dihydro-imidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  一些3,4-二取代-6,7-二氢咪唑并[2,1-b] [1,3]噻唑和3,4-二取代-7,8-二氢-6H-咪唑并[2,1- b] [1,3]噻嗪衍生物及其对F2408和5RP7细胞的细胞毒性评估

  摘要：

  本文介绍了3,4-二取代-6,7-二氢咪唑并[2,1-b] [1,3]噻唑和3,4-二取代-7,8-二氢-6H-咪唑并[2]的合成，1-b] [1,3]噻嗪类化合物，分别在5,6和2,3位具有取代或未取代的苯环，它们通过非癌细胞（F2408）和癌细胞（5RP7）的细胞毒性作用，及其详细信息1 H和13 C核磁共振（NMR）光谱表征。在碳酸钾（K 2 CO 3）存在下，通过将4,5-二芳基-咪唑-2-硫酮和二卤代烷烃（即1,2-二卤代乙烷或1,3-二卤代丙烷）环化获得标题化合物。在 N，N -二甲基甲酰胺（DMF）。4，5-二芳基-咪唑-2-硫酮是通过将α-羟基酮（酰基辅酶）缩合而制得的，而α-羟基酮是通过将氰化物用醛处理醛与硫脲在AcOH中缩合而制得的。咪唑并[2,1-b] [1,3]噻唑和咪唑并[2,1-b] [1,3]噻嗪衍生物的结构已通过红外（IR），1 H-NMR和13 C-确证。

  DOI：

  10.1007/s00044-008-9090-7

文献信息

• 5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents
  作者：Paul E. Bender、David Hill、Priscilla H. Offen、Kazys Razgaitis、Patricia Lavanchy、Orum D. Stringer、Blaine M. Sutton、Don E. Griswold、Michael DiMartino

  DOI：10.1021/jm00147a008

  日期：1985.9

  A series of substituted 5,6-diaryl-2,3-dihydroimidazo[2,1-b]thiazoles were synthesized and evaluated in the rat adjuvant-induced arthritis and mouse oxazolone-induced contact sensitivity assays to determine the potential of these compounds for use as immunoregulatory antiinflammatory agents. This class of compounds was derived by combining salient structural features of the antiinflammatory agent flumizole and the immunoregulatory drug levamisole. Unlike the latter two, a number of compounds in the target series were found to possess the desired combination of activities. Exploration of structure-activity relationships in the adjuvant-induced arthritic rat assay revealed that optimal potency was exhibited by symmetrically substituted 5,6-diaryl compounds having one of the following alkyl heteroatom or halogen functions at the para position: methoxy, ethoxy, methylthio, N-ethyl-N-methylamino, fluoro, or chloro. Scrambling of these two substituent classes to yield the asymmetrically substituted 5,6-diaryl compounds resulted in potent activity only with the 5-alkyl heteroatom, 6-halo-substituted regioisomers. However in the oxazolone-induced contact sensitivity assay, no consistent relationship of variation in activity with structural change was apparent. The initial target compound 5,6-bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole (1) was compared with its progenitors in additional models of inflammation and immunoregulation.