6-(3,4-二甲氧基苯基)咪唑并[2,1-b]噻唑-5-甲醛 | 562792-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-(3,4-二甲氧基苯基)咪唑并[2,1-b]噻唑-5-甲醛
• 英文名称: 6-(3,4-dimethoxyphenyl)imidazo[2,1-b]thiazol-5-carbaldehyde
• 英文别名: 6-(3,4-Dimethoxyphenyl)imidazo[2,1-b]thiazole-5-carbaldehyde；6-(3,4-dimethoxyphenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 562792-76-1
• 化学式: C₁₄H₁₂N₂O₃S
• 分子量: 288.327
• InChiKey: PMRNVQUGKAAULA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  6-(3,4-二甲氧基苯基)咪唑并[2,1-b]噻唑-5-甲醛 、 肼甲酰亚胺酰胺一氯化氢 以 乙醇 为溶剂， 以96%的产率得到2-[(E)-[6-(3,4-dimethoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]methylideneamino]guanidine;hydrochloride
  参考文献：
  名称：

  潜在的抗肿瘤药。37.由咪唑并[2，1-b]噻唑和新的杂环系统噻唑并[2′，3′：2，3]咪唑并[4，5-c]喹啉合成胍基hydr并具有抗肿瘤活性。

  摘要：

  本文报道了由咪唑并[2,1-b]噻唑和杂环新体系噻唑并[2'，3'：2,3]咪唑并[4,5-c]喹啉合成的新胍hydr及其抗肿瘤活性。这些化合物已在美国国家癌症研究所测试为潜在的抗肿瘤药物。研究了2-氯-6-（2,5-二甲氧基-4-硝基苯基）咪唑并[2,1-b]噻唑-5-甲醛的胍hydr的作用（41），发现其是抑制剂线粒体呼吸链复合物III的合成，能够诱导细胞株HT29和HL60凋亡。

  DOI：

  10.1021/jm040888s
• 作为产物：
  描述：

  在 盐酸 、 三氯氧磷 作用下， 以 氯仿 、 水 为溶剂， 反应 1.0h， 生成 6-(3,4-二甲氧基苯基)咪唑并[2,1-b]噻唑-5-甲醛
  参考文献：
  名称：

  咪唑并噻唑-查尔酮衍生物的合成作为抗癌和凋亡诱导剂

  摘要：

  合成了新型的咪唑并[2,1– b ]噻唑查尔酮衍生物，并对其抗癌活性进行了评估。这些查耳酮衍生物显示出令人鼓舞的活性，log GI 50值为-7.51至-4.00。研究了这些衍生物对MCF-7细胞系的详细生物学特性。有趣的是，这些查耳酮衍生物诱导了G 0 / G 1期细胞周期停滞，下调了G 1。细胞周期调节蛋白，如细胞周期蛋白D1和细胞周期蛋白E1，以及CDK4的上调。此外，这些化合物还引发了细胞凋亡的特征性特征，例如p53，p21和p27水平的升高，NF-κB的抑制以及caspase-9的上调。这些查耳酮衍生物之一3 d可能非常适合单独或与现有疗法组合进行详细的生物学研究。

  DOI：

  10.1002/cmdc.201000346

文献信息

• 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.
• Synthesis of Imidazothiazole-Chalcone Derivatives as Anticancer and Apoptosis Inducing Agents
  作者：Ahmed Kamal、D. Dastagiri、M. Janaki Ramaiah、J. Surendranadha Reddy、E. Vijaya Bharathi、Chatla Srinivas、S. N. C. V. L. Pushpavalli、Dhananjaya Pal、Manika Pal-Bhadra

  DOI：10.1002/cmdc.201000346

  日期：2010.11.8

  class of imidazo[2,1‐b]thiazole chalcone derivatives were synthesized and evaluated for their anticancer activity. These chalcone derivatives show promising activity, with log GI50 values ranging from −7.51 to −4.00. The detailed biological aspects of these derivatives toward the MCF‐7 cell line were studied. Interestingly, these chalcone derivatives induced G0/G1‐phase cell‐cycle arrest, down‐regulation

  合成了新型的咪唑并[2,1– b ]噻唑查尔酮衍生物，并对其抗癌活性进行了评估。这些查耳酮衍生物显示出令人鼓舞的活性，log GI 50值为-7.51至-4.00。研究了这些衍生物对MCF-7细胞系的详细生物学特性。有趣的是，这些查耳酮衍生物诱导了G 0 / G 1期细胞周期停滞，下调了G 1。细胞周期调节蛋白，如细胞周期蛋白D1和细胞周期蛋白E1，以及CDK4的上调。此外，这些化合物还引发了细胞凋亡的特征性特征，例如p53，p21和p27水平的升高，NF-κB的抑制以及caspase-9的上调。这些查耳酮衍生物之一3 d可能非常适合单独或与现有疗法组合进行详细的生物学研究。
• Potential Antitumor Agents. 37. Synthesis and Antitumor Activity of Guanylhydrazones from Imidazo[2,1-<i>b</i>]thiazoles and from the New Heterocyclic System Thiazolo[2‘,3‘:2,3]imidazo[4,5-<i>c</i>]quinoline
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Giorgio Lenaz、Romana Fato、Christian Bergamini、Giovanna Farruggia

  DOI：10.1021/jm040888s

  日期：2005.4.1

  synthesis and antitumor activity of new guanylhydrazones from imidazo[2,1-b]thiazoles and from the new heterocyclic system thiazolo[2',3':2,3]imidazo[4,5-c]quinoline. The compounds were tested as potential antitumor agents at the National Cancer Institute. The effect of the guanylhydrazone of 2-chloro-6-(2,5-dimethoxy-4-nitrophenyl)imidazo[2,1-b]thiazole-5-carbaldehyde (41) was investigated, and it was

  本文报道了由咪唑并[2,1-b]噻唑和杂环新体系噻唑并[2'，3'：2,3]咪唑并[4,5-c]喹啉合成的新胍hydr及其抗肿瘤活性。这些化合物已在美国国家癌症研究所测试为潜在的抗肿瘤药物。研究了2-氯-6-（2,5-二甲氧基-4-硝基苯基）咪唑并[2,1-b]噻唑-5-甲醛的胍hydr的作用（41），发现其是抑制剂线粒体呼吸链复合物III的合成，能够诱导细胞株HT29和HL60凋亡。