6-(4-Methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole | 92754-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-Methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 92754-18-2
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: WJVODFDKCHPAJF-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C(Solv: methanol (67-56-1))
• 沸点：
  451.2±47.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-Methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole 在 三氯化铝 作用下， 以 xylene 为溶剂， 反应 5.0h， 以58%的产率得到6-(4-hydroxyphenyl)-2,3-dihydro-imidazo[2,1-b]thiazole
  参考文献：
  名称：

  6-(Hydroxyphenyl)imidazo[2,1-b]thiazoles as Potential Antiinflammatory Agents: Effects on Human Neutrophil Functions

  摘要：

  报道了从相应的甲氧基衍生物合成与左旋咪唑相关的6-(羟基苯基)咪唑并[2,1-b]噻唑。这些化合物在体外中性粒细胞活化方面进行了测试，即由趋化剂诱导的运动、由激动剂引发的超氧化物生成和溶菌酶脱颗粒。这些功能在细胞脉冲后经不同浓度药物评估。一些衍生物显示出显著的抑制作用，在某些情况下比母化合物更强效。

  DOI：

  10.1135/cccc20000267
• 作为产物：
  描述：

  2-(2-imino-thiazolidin-3-yl)-1-(4-methoxy-phenyl)-ethanone; hydrobromide 在 氢溴酸 作用下， 反应 1.0h， 生成 6-(4-Methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  Andreani; Rambaldi; Bonazzi, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 219 - 222

  摘要：

  DOI：

文献信息

• Iodine-promoted direct sulfenylation of 2,3-dihydroimidazo[2,1-b]thiazoles with disulfides
  作者：Wenjie Liu、Shaohua Wang、Yuzhen Chen、Yanling Huang、Ziying Li、Anda Wang

  DOI：10.1080/10426507.2015.1073278

  日期：2016.5.3

  ABSTRACT A novel and facile method for the direct sulfenylation of 2,3-dihydroimidazo[2,1-b]thiazoles with disulfides has been developed. The transformation is promoted by iodine under metal-free conditions, providing the corresponding products in moderate to good yields. GRAPHICAL ABSTRACT

  摘要 已开发出一种用二硫化物直接对 2,3-二氢咪唑并 [2,1-b] 噻唑进行磺基化的新型简便方法。在无金属条件下，碘促进转化，以中等至良好的收率提供相应的产品。图形概要
• Synthetic and mechanistic studies on the preparation of pyridyl-substituted imidazothiazoles
  作者：Ivan Lantos、Kerry Gombatz、Michael McGuire、Lendon Pridgen、James Remich、Susan Shilcrat

  DOI：10.1021/jo00253a012

  日期：1988.9
• 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.
• ANDREANI, A.;RAMBALDI, M.;BONAZZI, D.;LELLI, G.;BOSSA, R.;GALATULAS, I., EUR. J. MED. CHEM., 1984, 19, N 3, 219-222
  作者：ANDREANI, A.、RAMBALDI, M.、BONAZZI, D.、LELLI, G.、BOSSA, R.、GALATULAS, I.

  DOI：——

  日期：——
• LANTOS, IVAN;GOMBATZ, KERRY;MCGUIRE, MICHAEL;PRIDGEN, LENDON;REMICH, JAME+, J. ORG. CHEM., 53,(1988) N 18, C. 4223-4227
  作者：LANTOS, IVAN、GOMBATZ, KERRY、MCGUIRE, MICHAEL、PRIDGEN, LENDON、REMICH, JAME+

  DOI：——

  日期：——