2-methyl-6-(2,5-dimethoxyphenyl)imidazo[2,1-b]thiazole-5-carboxaldehyde | 143951-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-6-(2,5-dimethoxyphenyl)imidazo[2,1-b]thiazole-5-carboxaldehyde
• 英文别名: 6-(2,5-Dimethoxyphenyl)-2-methylimidazo[2,1-B]thiazole-5-carboxaldehyde；6-(2,5-dimethoxyphenyl)-2-methylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 143951-31-9
• 化学式: C₁₅H₁₄N₂O₃S
• 分子量: 302.354
• InChiKey: GDCZRKJSNGIGNN-UHFFFAOYSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氯氧化吲哚 、 2-methyl-6-(2,5-dimethoxyphenyl)imidazo[2,1-b]thiazole-5-carboxaldehyde 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 (3E)-5-chloro-3-[[6-(2,5-dimethoxyphenyl)-2-methylimidazo[2,1-b][1,3]thiazol-5-yl]methylidene]-1H-indol-2-one
  参考文献：
  名称：

  Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-Imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones: Selectivity against Colon Tumor Cells and Effect on Cell Cycle-Related Events

  摘要：

  The synthesis of new 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones is reported. The antitumor activity was evaluated according to the protocols available at the National Cancer Institute (NCI), Bethesda, MD. To investigate the mechanism of action of the most potent antitumor agent of this series, its effect on growth of HT-29 colon carcinoma cells was studied. Its ability to inhibit cellular proliferation was mediated by cell cycle arrest at the G2/M phase, accompanied by inhibition of ornithine decarboxylase (ODC), the limiting enzyme of polyamine synthesis, and followed by induction of apoptosis.

  DOI：

  10.1021/jm800827q
• 作为产物：
  描述：

  6-(2,5-Dimethoxy-phenyl)-2-methyl-imidazo[2,1-b]thiazole 、 N,N-二甲基甲酰胺 在 吡啶 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 2-methyl-6-(2,5-dimethoxyphenyl)imidazo[2,1-b]thiazole-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis and cardiotonic activity of 2,5-dimethyoxyphenylimidazo[2,1-b]thiazoles

  摘要：

  DOI：

  10.1016/0223-5234(92)90159-x

文献信息

• 4-Imidazo[2,1-b]thiazole-1,4-DHPs and neuroprotection: preliminary study in hits searching
  作者：Alberto Leoni、Maria Frosini、Alessandra Locatelli、Matteo Micucci、Claudio Carotenuto、Miriam Durante、Sandro Cosconati、Roberta Budriesi

  DOI：10.1016/j.ejmech.2019.02.075

  日期：2019.5

  particular the strategy adopted for designing the compounds involves the imidazo[2,1-b]thiazole nucleus. The observed properties show that substituents at C2 and C6 of the bicyclic scaffold are able to influence the cardiovascular parameters and the neuroprotective activity. In comparison to nifedipine, a set of derivatives such as compound 6, showed a neuroprotective profile of particular interest.

  在目前的工作中，我们描述了4-咪唑并[2,1 - b ]噻唑-1,4-二氢吡啶类重点文库的合成，表征和神经保护作用的评估。此外，在心脏组织和血管平滑肌中对新的二氢吡啶进行了功能性体外测定，以确定它们在抵消神经退行性变中的可能选择性。特别是，设计化合物所采用的策略涉及咪唑并[2,1- b ]噻唑核。观察到的性质表明，双环支架的C2和C6处的取代基能够影响心血管参数和神经保护活性。与硝苯地平相比，一组衍生物如化合物6表现出特别重要的神经保护作用。
• Imidazo[2,1-<i>b</i>]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity
  作者：Roberta Budriesi、Pierfranco Ioan、Alessandra Locatelli、Sandro Cosconati、Alberto Leoni、Maria P. Ugenti、Aldo Andreani、Rosanna Di Toro、Andrea Bedini、Santi Spampinato、Luciana Marinelli、Ettore Novellino、Alberto Chiarini

  DOI：10.1021/jm070681+

  日期：2008.3.1

  The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1-b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.
• Ligand Based Approach to L-Type Calcium Channel by Imidazo[2,1-<i>b</i>]thiazole-1,4-Dihydropyridines: from Heart Activity to Brain Affinity
  作者：Alessandra Locatelli、Sandro Cosconati、Matteo Micucci、Alberto Leoni、Luciana Marinelli、Andrea Bedini、Pierfranco Ioan、Santi Mario Spampinato、Ettore Novellino、Alberto Chiarini、Roberta Budriesi

  DOI：10.1021/jm301839q

  日期：2013.5.23

  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.
• Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and 3-(5-Imidazo[2,1-<i>b</i>]thiadiazolylmethylene)-2-indolinones: Selectivity against Colon Tumor Cells and Effect on Cell Cycle-Related Events
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Manuela Voltattorni、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Robert H. Shoemaker

  DOI：10.1021/jm800827q

  日期：2008.12.11

  The synthesis of new 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones is reported. The antitumor activity was evaluated according to the protocols available at the National Cancer Institute (NCI), Bethesda, MD. To investigate the mechanism of action of the most potent antitumor agent of this series, its effect on growth of HT-29 colon carcinoma cells was studied. Its ability to inhibit cellular proliferation was mediated by cell cycle arrest at the G2/M phase, accompanied by inhibition of ornithine decarboxylase (ODC), the limiting enzyme of polyamine synthesis, and followed by induction of apoptosis.
• Synthesis and cardiotonic activity of 2,5-dimethyoxyphenylimidazo[2,1-b]thiazoles
  作者：A Andreani、M Rambaldi、A Locatelli、R Bossa、I Galatulas、M Ninci

  DOI：10.1016/0223-5234(92)90159-x

  日期：1992.6