5-phenyl-6-(4-methoxyphenyl)-2,3-dihydroimidazo<2,1-b>thiazole | 87532-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-phenyl-6-(4-methoxyphenyl)-2,3-dihydroimidazo<2,1-b>thiazole
• 英文别名: 6-(4-methoxy-phenyl)-5-phenyl-2,3-dihydro-imidazo[2,1-b]thiazole；6-(p-anisyl)-5-phenyl-2,3-dihydroimidazo[2,1-b]thiazole；6-(4-Methoxyphenyl)-5-phenyl-2,3-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 87532-36-3
• 化学式: C₁₈H₁₆N₂OS
• 分子量: 308.404
• InChiKey: XROYKSRASNUVSS-UHFFFAOYSA-N

物化性质

• 沸点：
  498.7±47.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)-1-苯基乙酮 在 3 A molecular sieve 、 溴 作用下， 以 四氯化碳 、 乙腈 为溶剂， 生成 5-phenyl-6-(4-methoxyphenyl)-2,3-dihydroimidazo<2,1-b>thiazole
  参考文献：
  名称：

  5,6-二芳基-2,3-二氢咪唑并[2,1-b]噻唑的抗炎活性。异构的4-吡啶基和4-取代的苯基衍生物。

  摘要：

  通过混合安息香-咪唑并硫醇途径制备异构5（6）-（4-吡啶基）-和6（5）-（4-取代苯基）-2,3-二氢咪唑并[2,1-b]噻唑。通过光谱比较将它们的结构分配给已建立取代模式的化合物。通过X射线分析确认了结构分配。通过佐剂关节炎大鼠测定法对化合物的抗炎活性的检查显示，一个类似系列的化合物的功效显着高于其异构体。在恶唑酮诱导的接触敏感性模型中反映出，这种选择性与刺激细胞介导的免疫能力平行。提出了需要至少三个相互作用位点的药物-受体复合物。

  DOI：

  10.1021/jm00367a014

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.
• US4263311A
  申请人：——

  公开号：US4263311A

  公开（公告）日：1981-04-21
• Antiinflammatory activity of 5,6-diaryl-2,3-dihydroimidazo[2,1-b]thiazoles. Isomeric 4-pyridyl and 4-substituted-phenyl derivatives
  作者：I. Lantos、P. E. Bender、K. A. Razgaitis、B. M. Sutton、M. J. DiMartino、D. E. Griswold、D. T. Walz

  DOI：10.1021/jm00367a014

  日期：1984.1

  Isomeric 5(6)-(4-pyridyl)- and 6(5)-(4-substituted-phenyl)-2,3-dihydroimidazo[2,1-b]thiazoles were prepared by a mixed benzoin-imidazothione route, and their structures were assigned by spectral comparison to compounds of established substitution pattern. The structural assignment was confirmed by X-ray analysis. Examination of the compounds for antiinflammatory activity by an adjuvant arthritic rat

  通过混合安息香-咪唑并硫醇途径制备异构5（6）-（4-吡啶基）-和6（5）-（4-取代苯基）-2,3-二氢咪唑并[2,1-b]噻唑。通过光谱比较将它们的结构分配给已建立取代模式的化合物。通过X射线分析确认了结构分配。通过佐剂关节炎大鼠测定法对化合物的抗炎活性的检查显示，一个类似系列的化合物的功效显着高于其异构体。在恶唑酮诱导的接触敏感性模型中反映出，这种选择性与刺激细胞介导的免疫能力平行。提出了需要至少三个相互作用位点的药物-受体复合物。