6-对甲苯基咪唑并[2,1-b]噻唑-5-甲醛 | 82588-42-9

• 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-对甲苯基咪唑并[2,1-b]噻唑-5-甲醛
• 中文别名: 6-(4-甲苯)咪唑并[2,1-B][1,3]噻唑-5-甲醛
• 英文名称: 5-Formyl-6-p-tolylimidazo<2,1-b>thiazole
• 英文别名: 6-(p-tolyl)imidazo[2,1-b]thiazole-5-carbaldehyde；5-Formyl-6-p-tolylimidazo[2,1-b]thiazole；6-(4-Methylphenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 82588-42-9
• 化学式: C₁₃H₁₀N₂OS
• mdl: MFCD03425723
• 分子量: 242.301
• InChiKey: NUEBUPJVOGWDTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169°C
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  6-对甲苯基咪唑并[2,1-b]噻唑-5-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 [6-(4-甲基苯基)咪唑并[2,1-b][1,3]噻唑-5-基]甲醇
  参考文献：
  名称：

  潜在的抗肿瘤剂，VII. 5-取代的 6-苯基咪唑 [2,1-b] 噻唑

  摘要：

  报道了用于合成 5-甲酰基咪唑并 [2,1-b] 噻唑 7-12 的 Vilsmeier 反应，该反应在 6 位带有对取代的苯环。这些化合物用于合成缩氨基硫腙 7a-12a、甲苯磺酰腙7b-12b 和 5-羟甲基衍生物 13-18，进而用作制备甲基氨基甲酸 13a-18a、乙基氨基甲酸 13b-18b 和乙酸的起始原料酯 13c-18c。报告了 P-388 白血病测试的初步结果。

  DOI：

  10.1002/ardp.19823150511
• 作为产物：
  描述：

  2-溴-4'-甲基苯乙酮 在 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 22.0h， 生成 6-对甲苯基咪唑并[2,1-b]噻唑-5-甲醛
  参考文献：
  名称：

  Human constitutive androstane receptor agonist DL5016: A novel sensitizer for cyclophosphamide-based chemotherapies

  摘要：

  The DNA alkylating prodrug cyclophosphamide (CPA), alone or in combination with other agents, is one of the most commonly used anti-cancer agents. As a prodrug, CPA is activated by cytochrome P450 2B6 (CYP2B6), which is transcriptionally regulated by the human constitutive androstane receptor (hCAR). Therefore, hCAR agonists represent novel sensitizers for CPA-based therapies. Among known hCAR agonists, compound 6-(4-chlorophenyl)imidazo-[2,1-b]thiazole-5-carbaldehyde-O-(3,4-dichlorobenzyl) oxime (CITCO) is the most potent and broadly utilized in biological studies. Through structural modification of CITCO, we have developed a novel compound DL5016 (32), which has an EC50 value of 0.66 mu M and E-MAX value of 4.9 when activating hCAR. DL5016 robustly induced the expression of hCAR target gene CYP2B6, at both the mRNA and protein levels, and caused translocation of hCAR from the cytoplasm to the nucleus in human primary hepatocytes. The effects of DL5016 were highlighted by dramatically enhancing the efficacy of CPA-based cytotoxicity to non-Hodgkin lymphoma cells. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.06.031

文献信息

• Novel imidazo[2,1-b]thiazoles and imidazo[1,2-a]pyridines tethered with indolinone motif as VEGFR-2 inhibitors and apoptotic inducers: Design, synthesis and biological evaluations
  作者：Mahmoud S. Elkotamy、Mohamed K. Elgohary、Sara T. Al-Rashood、Hadia Almahli、Wagdy M. Eldehna、Hatem A. Abdel-Aziz

  DOI：10.1016/j.bioorg.2024.107644

  日期：2024.10

  The current study investigates the anticancer and VEGFR-2 inhibitory activities of 16 novel indolinone-grafted imidazo[2,1-]thiazole and imidazo[1,2-]pyridine derivatives ( and ). The structures of these target compounds were confirmed using elemental and spectral analyses. All compounds were evaluated for their VEGFR-2 inhibitory activity in vitro, with eight compounds demonstrating promising results

  目前的研究调查了 16 种新型吲哚酮接枝咪唑并[2,1-]噻唑和咪唑并[1,2-]吡啶衍生物的抗癌和 VEGFR-2 抑制活性 ( 和 )。使用元素和光谱分析确认了这些目标化合物的结构。所有化合物均在体外评估了 VEGFR-2 抑制活性，其中 8 种化合物显示出良好的结果，IC 值在亚微摩尔范围内 (0.22 μM – 0.95 μM)。此外，还使用 ​​MTT 测定对两种乳腺癌细胞系 MCF-7 和 MDA-MB-231 评估了这些化合物的抗癌潜力。与参考药物顺铂 (IC = 11.50 µM) 相比，化合物 、 、 和 对 MDA-MB-231 细胞表现出优异的性能（IC 分别为 9.79、8.78、8.35 和 10.88 µM）。基于其一致的 VEGFR-2 抑制活性，选择化合物 、 、 和 进行进一步分析。 VEGFR-2（PDB ID：4AGD）的分子对接研究揭示了与共结晶配体
• DL5050, a Selective Agonist for the Human Constitutive Androstane Receptor
  作者：Dongdong Liang、Linhao Li、Caitlin Lynch、Benjamin Diethelm-Varela、Menghang Xia、Fengtian Xue、Hongbing Wang

  DOI：10.1021/acsmedchemlett.9b00079

  日期：2019.7.11

  The constitutive androstane receptor (CAR) is a xenobiotic sensor governing the transcription of genes involved in drug disposition, energy homeostasis, and cell proliferation. However, currently available human CAR (hCAR) agonists are nonselective, which commonly activate hCAR along with other nuclear receptors, especially the closely related human pregnane X receptor (hPXR). Using a well-known hCAR agonist CITCO as a template, we report our efforts in the discovery of a potent and highly selective hCAR agonist. Two of the new compounds of the series, 18 and 19 (DL5050), demonstrated excellent potency and selectivity for hCAR over hPXR. DL5050 preferentially induced the expression of CYP2B6 (target of hCAR) over CYP3A4 (target of hPXR) on both the mRNA and protein levels. The selective hCAR agonist DL5050 represents a valuable tool molecule to further define the biological functions of hCAR, and may also be used as a new lead in the discovery of hCAR agonists for various therapeutic applications.
• Dihydropyridines bearing an imidazo[2,1-b]thiazole system
  作者：A Andreani、A Leoni、M Rambaldi、A Locatelli、R Bossa、I Galatulas、M Chiericozzi、M Bissoli

  DOI：10.1016/s0223-5234(97)87542-3

  日期：1997.1

  This paper reports the synthesis of imidazo[2,1-b]thiazoles, bearing a dihydropyridine ring at the 5 or 6 position, which were tested for antiarrhythmic, inotropic and chronotropic activities. Nine of the ten compounds bearing double bond at the 2,3 position and the same dihydropyridine as nifedipine at the 5 position, were antiarrhythmic; moreover one of them (bearing a methyl group at the 2 position) was devoid of negative inotropic activity.
• Synthesis and diuretic activity of imidazo[2,1-b]thiazole acetohydrazones
  作者：Aldo Andreani、Mirella Rambaldi、Giuseppe Mascellani、Pierluigi Rugarli

  DOI：10.1016/0223-5234(87)90169-3

  日期：1987.1
• Potential antitumor agents. 21. Structure determination and antitumor activity of imidazo[2,1-b]thiazole guanylhydrazones
  作者：Aldo Andreani、Mirella Rambaldi、Alessandra Locatelli、Rosaria Bossa、Alessandra Fraccari、Iraklis Galatulas

  DOI：10.1021/jm00102a018

  日期：1992.11