6-(2-Thienyl)-2,3-dihydroimidazo[2,1-B][1,3]thiazole | 163851-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: 6-(2-Thienyl)-2,3-dihydroimidazo[2,1-B][1,3]thiazole
• 英文别名: 6-thiophen-2-yl-2,3-dihydroimidazo[2,1-b][1,3]thiazole
• CAS: 163851-60-3
• 化学式: C₉H₈N₂S₂
• mdl: MFCD02634214
• 分子量: 208.308
• InChiKey: SSOPPFVENQERAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 6-(2-Thienyl)-2,3-dihydroimidazo[2,1-B][1,3]thiazole 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 6-Thiophen-2-yl-2,3-dihydroimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
  参考文献：
  名称：

  New Antitumor Imidazo[2,1-b]thiazole Guanylhydrazones and Analogues¹

  摘要：

  The synthesis of new antitumor 6-substituted imidazothiazole guanylhydrazones is described. Moreover, a series of compounds with a different basic chain at the 5 position were prepared. Finally, the replacement of the thiazole ring in the imidazothiazole system was also considered. All the new compounds prepared were submitted to the NCI cell line screen for evaluation of their antitumor activity. A few selected compounds were submitted to additional biological studies concerning effects on the cell cycle, apoptosis, and mitochondria.

  DOI：

  10.1021/jm701246g
• 作为产物：
  描述：

  2-(2-imino-thiazolidin-3-yl)-1-thiophen-2-yl-ethanone; hydrobromide 在 氢溴酸 作用下， 生成 6-(2-Thienyl)-2,3-dihydroimidazo[2,1-B][1,3]thiazole
  参考文献：
  名称：

  噻吩咪唑并[2,1-b]噻唑类化合物是线粒体NADH脱氢酶的抑制剂。

  摘要：

  报道了6-取代的5-（噻吩乙烯基）咪唑并[2，1-b]噻唑和6-噻吩并咪唑并[2，1-b]噻唑的合成。测试这些化合物作为线粒体膜NADH脱氢酶的NADH特异性抑制剂：泛醌（UBQ）还原酶活性。6-噻吩并咪唑并[2,1-b]噻唑在哺乳动物中比线虫线粒体更有效，并且2-甲基-6-（2-噻吩基）咪唑并[2,1-b]噻唑的平均滴度为0.11 mM。 （10）。该化合物与泛醌底物不竞争，并与鱼藤酮互斥，但与piericidin和其他几种NADH脱氢酶抑制剂互斥，但互斥。在5-（噻吩乙烯基）咪唑并噻唑系列中，（E）-6-氯-5-（2-噻吩乙烯基）咪唑并[2,1-b]噻唑的氢溴酸盐（E-5。

  DOI：

  10.1021/jm00007a006

文献信息

• New Antitumor Imidazo[2,1-<i>b</i>]thiazole Guanylhydrazones and Analogues¹
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Giovanna Farruggia、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Norman S. Radin、Robert H. Shoemaker

  DOI：10.1021/jm701246g

  日期：2008.2.1

  The synthesis of new antitumor 6-substituted imidazothiazole guanylhydrazones is described. Moreover, a series of compounds with a different basic chain at the 5 position were prepared. Finally, the replacement of the thiazole ring in the imidazothiazole system was also considered. All the new compounds prepared were submitted to the NCI cell line screen for evaluation of their antitumor activity. A few selected compounds were submitted to additional biological studies concerning effects on the cell cycle, apoptosis, and mitochondria.
• Thienylimidazo[2,1-b]thiazoles as Inhibitors of Mitochondrial NADH Dehydrogenase
  作者：Aldo Andreani、Mirella Rambaldi、Alberto Leoni、Alessandra Locatelli、Anna Ghelli、Marina Ratta、Bruna Benelli、Mauro Degli Esposti

  DOI：10.1021/jm00007a006

  日期：1995.3

  synthesis of 6-substituted 5-(thienylvinyl)imidazo[2,1-b]thiazoles and 6-thienylimidazo[2,1-b]thiazoles is reported. These compounds were tested as specific inhibitors of the NADH: ubiquinone (UBQ) reductase activity of NADH dehydrogenase in mitochondrial membranes. The 6-thienylimidazo[2,1-b]thiazoles were more potent in mammalian than in nematode mitochondria and had an average titer of 0.11 mM for 2-

  报道了6-取代的5-（噻吩乙烯基）咪唑并[2，1-b]噻唑和6-噻吩并咪唑并[2，1-b]噻唑的合成。测试这些化合物作为线粒体膜NADH脱氢酶的NADH特异性抑制剂：泛醌（UBQ）还原酶活性。6-噻吩并咪唑并[2,1-b]噻唑在哺乳动物中比线虫线粒体更有效，并且2-甲基-6-（2-噻吩基）咪唑并[2,1-b]噻唑的平均滴度为0.11 mM。 （10）。该化合物与泛醌底物不竞争，并与鱼藤酮互斥，但与piericidin和其他几种NADH脱氢酶抑制剂互斥，但互斥。在5-（噻吩乙烯基）咪唑并噻唑系列中，（E）-6-氯-5-（2-噻吩乙烯基）咪唑并[2,1-b]噻唑的氢溴酸盐（E-5。