6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b]thiazole-5-carbaldehyde | 1015756-80-5

• 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-(3,4,5-trimethoxyphenyl)imidazo[2,1-b]thiazole-5-carbaldehyde
• 英文别名: 6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 1015756-80-5
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: XUVICNSTAOCZIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-甲氧基吲哚酮 、 6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b]thiazole-5-carbaldehyde 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 5-methoxy-3-[[6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]methylidene]-1H-indol-2-one
  参考文献：
  名称：

  Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action

  摘要：

  The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.

  DOI：

  10.1021/jm2012694
• 作为产物：
  描述：

  6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b]thiazole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 以93%的产率得到6-(3,4,5-trimethoxyphenyl)imidazo[2,1-b]thiazole-5-carbaldehyde
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity

  摘要：

  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.

  DOI：

  10.1021/jm070681+

文献信息

• Inhibition of MDR1 activity and induction of apoptosis by analogues of nifedipine and diltiazem: an in vitro analysis
  作者：Maurizio Viale、Cinzia Cordazzo、Daniela de Totero、Roberta Budriesi、Camillo Rosano、Alberto Leoni、Pierfranco Ioan、Cinzia Aiello、Michela Croce、Aldo Andreani、Mirella Rambaldi、Patrizia Russo、Alberto Chiarini、Domenico Spinelli

  DOI：10.1007/s10637-009-9340-7

  日期：2011.2

  fluorescein isothiocyanate (FITC)-Annexin-V/propidium iodide (PI) staining and the caspase activity determination. Our results demonstrate that compounds 1 and 2, at concentrations showing a very low (5%) or absent inhibition of cell proliferation, in combination with doxorubicin enhance its antiproliferative activity (from 30% to 54% IC(50) reduction) in A2780/DX3 cells through an increase of doxorubicin

  我们在此报告了两种硝苯地平类化合物 1 和 2 在 A2780/DX3 细胞中逆转多药耐药性 1 (MDR1)，它们是 1,4-二氢吡啶 (1,4-DHPs) 钙通道库的一部分在 C-4 中带有不同取代的咪唑并 [2,1-b] 噻唑系统的调节剂。通过甲基噻唑四唑 (MTT) 测定、细胞荧光法和荧光显微镜，我们评估了它们在我们的细胞系统中逆转 MDR 的能力。此外，连同化合物3（地尔硫卓样8-(4-氯苯基)-5-甲基-8-[(2Z)-pent-2-en-1-yloxy]-8H-[1,2,4] oxadiazolo[3,4-c][1,4]thiazin-3-one) 我们通过 4',6-二脒基-2-苯基吲哚后的核形态分析，分析了它们在暴露于多柔比星后增强触发细胞凋亡的能力(DAPI), 异硫氰酸荧光素 (FITC)-膜联蛋白-V/碘化丙啶 (PI) 染色和半胱天冬酶活性测定。我们的结果表明，化合物
• Substituted 3-(5-Imidazo[2,1-<i>b</i>]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action
  作者：Aldo Andreani、Massimiliano Granaiola、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Giovanna Farruggia、Claudio Stefanelli、Lanfranco Masotti、Tam L. Nguyen、Ernest Hamel、Robert H. Shoemaker

  DOI：10.1021/jm2012694

  日期：2012.3.8

  The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.
• 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.