2-Methyl-6-thiophen-3-ylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde | 1012875-06-7

• 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: 2-Methyl-6-thiophen-3-ylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 1012875-06-7
• 化学式: C₁₁H₈N₂OS₂
• 分子量: 248.329
• InChiKey: NGXLBICSDWSRJD-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solvent: Ethanol)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methyl-6-thiophen-3-ylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde 、 乙酰乙酸甲酯 在 ammonium hydroxide 作用下， 以 异丙醇 为溶剂， 以12%的产率得到Dimethyl 2,6-dimethyl-4-(2-methyl-6-thiophen-3-ylimidazo[2,1-b][1,3]thiazol-5-yl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Ligand Based Approach to L-Type Calcium Channel by Imidazo[2,1-b]thiazole-1,4-Dihydropyridines: from Heart Activity to Brain Affinity

  摘要：

  The synthesis, characterization, and functional in vitro assay in cardiac and smooth muscle (vascular and nonvascular) of a series of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. To define the calcium blocker nature of the imidazo[2,1-b]thiazole-1,4-DHPs and their selectivity on Ca(v)1.2 and Ca(v)1.3 isoforms, we performed binding studies on guinea pig atrial and ventricular membranes on intact cells expressing the cloned Ca(v)1.2a subunit and on rat brain cortex. To get major insights into the reasons for the affinity for Ca(v)1.2 and/or Ca(v)1.3, molecular modeling studies were also undertaken. Some physicochemical and pharmacokinetic properties of selected compounds were calculated and compared. All the biological data collected and reported herein allowed us to rationalize the structure-activity relationship of the 4-imidazo[2,1-b]thiazole-1,4-DHPs and to identify which of these enhanced the activity at the central level.

  DOI：

  10.1021/jm301839q
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 2-Methyl-6-thiophen-3-ylimidazo[2,1-b][1,3]thiazole 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 2-Methyl-6-thiophen-3-ylimidazo[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