5,6-bis-(4-chloro-phenyl)-2,3-dihydro-imidazo[2,1-b]thiazole | 64997-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5,6-bis-(4-chloro-phenyl)-2,3-dihydro-imidazo[2,1-b]thiazole
• 英文别名: 5,6-Bis(4-chlorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 64997-47-3
• 化学式: C₁₇H₁₂Cl₂N₂S
• 分子量: 347.268
• InChiKey: ZZMHJXQBTKLHNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-氨基-2-噻唑啉 、 2-bromo-1,2-bis(4-chlorophenyl)ethanone 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以61%的产率得到5,6-bis-(4-chloro-phenyl)-2,3-dihydro-imidazo[2,1-b]thiazole
  参考文献：
  名称：

  5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents

  摘要：

  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.

  DOI：

  10.1021/jm00147a008

文献信息

• Diazaverbindungen und Verfahren zu deren Herstellung
  申请人：CIBA-GEIGY AG

  公开号：EP0019688A1

  公开（公告）日：1980-12-10

  Die Erfindung betrifft neue Diazaverbindungen, insbesondere 1,3-Diaza-cyclopent-2-ene der allgemeinen Formel(I) deren 1,3-Diaza-cyclopent-2-en-ring eine weitere Doppelbindung aufweisen kann, Alk Niederalkylen darstellt, welches das Thia- vom Aza-atom durch 2-4 Kohlenstoffatome trent, Ar1 und Ar2 unabhängig voneinander gegebenenfalls substituiertes Phenyl, Pyridyl oder Thienyl bedeuten und n 0, 1 oder 2 ist, mit der Maßgabe, daß mindestens einer der Reste Ar1 und Ar2 von Phenyl verschieden ist, wenn Alk Äthylen und der 1,3-Diaza-cyclopent-2-en-ring einen lmidazolring darstellt, und deren Salze, sowie Verfahren zu ihrer Herstellung. Die neuen Verbindungen können als Zwischenprodukte von Arzneimitteiwirkstoffen verwendet werden, insbesondere entzündungshemmenden und antirheumatischen Wirkstoffen.

  本发明涉及新的二氮杂环化合物，特别是通式（I）的 1，3-二氮杂环戊-2-烯 其中的 1，3-二氮杂-环戊-2-烯环可能具有另一个双键，Al 为低级亚烷基，代表与氮原子相隔 2-4 个碳原子的硫原子，Ar1 和 Ar2 各自代表任选取代的苯基、吡啶基或噻吩基，且 n 为 0、1 或 2、吡啶基或噻吩基，且 n 为 0、1 或 2，但当 Alk 为乙烯且 1，3-二氮杂-环戊-2-烯环为咪唑环时，Ar1 和 Ar2 中至少有一个基不是苯基。 新化合物可用作活性药物成分的中间体，特别是消炎药和抗风湿药。
• US4263311A
  申请人：——

  公开号：US4263311A

  公开（公告）日：1981-04-21
• 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.