2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole | 57772-04-0

• 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-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• 英文别名: 2-methyl-6-p-tolylimidazo[2,1-b][1,3,4]thiadiazole；2-methyl-6-p-tolyl-imidazo[2,1-b][1,3,4]thiadiazole；2-Methyl-6-p-tolylimidazo<2,1-b>-1,3,4-thiadiazol；2-Methyl-6-(p-tolyl)imidazo[2,1-b][1,3,4]thiadiazole；2-methyl-6-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• CAS: 57772-04-0
• 化学式: C₁₂H₁₁N₃S
• 分子量: 229.305
• InChiKey: QOLSAMOXFYESTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C(Solv: benzene (71-43-2))
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole 在 sodium thiosulfate 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 2-methyl-5-(5-methyl-1H-benzo[d]imidazol-2-yl)-6-p-tolylimidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Synthesis of imidazothiadiazole–benzimidazole conjugates as mitochondrial apoptosis inducers

  摘要：

  一系列咪唑噻二唑-苯并咪唑偶联物（3a-z）被合成并评估其对四种选择的人类癌细胞系的细胞毒活性。化合物3b和3y对ME-180（宫颈）细胞系表现出显著的抗增殖活性。

  DOI：

  10.1039/c4md00219a
• 作为产物：
  描述：

  2-(2-imino-5-methyl-[1,3,4]thiadiazol-3-yl)-1-p-tolyl-ethanone 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-methyl-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Pentimalli,L. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 777 - 787

  摘要：

  DOI：

文献信息

• Ionic liquid-promoted one-pot synthesis of thiazole–imidazo[2,1-b][1,3,4]thiadiazole hybrids and their antitubercular activity
  作者：Jurupula Ramprasad、Nagabhushana Nayak、Udayakumar Dalimba、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1039/c5md00346f

  日期：——

  The anti-TB activity of new thiazole–imidazo[2,1-b][1,3,4]thiadiazoles, which are synthesized via one-pot synthesis, is comparable with that of standard drugs.

  新噻唑-咪唑[2,1-b][1,3,4]噻二唑类化合物的抗结核活性，通过一锅法合成，与标准药物相当。
• Synthesis and biological evaluation of new imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole derivatives
  作者：Jurupula Ramprasad、Nagabhushana Nayak、Udayakumar Dalimba、Perumal Yogeeswari、Dharmarajan Sriram、S.K. Peethambar、Rajeshwara Achur、H. S. Santosh Kumar

  DOI：10.1016/j.ejmech.2015.03.024

  日期：2015.5

  In this report, we describe the synthesis and biological evaluation of a new series of 2-(imidazo[2,1-b][1,3,4]thiadiazol-5-yl)-1H-benzimidazole derivatives (5a-ac). The molecules were analyzed by 1H NMR, 13C NMR, mass spectral and elemental data. The structure of one of the pre-final compounds, 6-(4-methoxyphenyl)-2-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (4d) and that of a

  在本报告中，我们描述了一系列新的2-（咪唑并[2,1- b ] [1,3,4]噻二唑-5-基）-1 H-苯并咪唑衍生物（5a-ac）。通过1 H NMR，13 C NMR，质谱和元素数据分析分子。最终化合物之一的结构为6-（4-甲氧基苯基）-2-（4-甲基苯基）咪唑并[2,1- b ] [1,3,4]噻二唑-5-甲醛（4d）和目标化合物的2- [2-甲基-6-（4-甲基苯基）咪唑并[2,1- b ] [1,3,4]噻二唑-5-基] -1 H-苯并咪唑（5aa）由单晶XRD研究确认。筛选所有目标化合物的针对结核分枝杆菌H37Rv菌株的体外抗结核活性。29种化合物中的7种（5c，5d，5l，5p，5r，5z和5aa）显示出有效的抗结核活性，MIC为3.125μg/ mL。咪唑并[2,1- b ]中的对位取代苯基（对甲苯基或对氯苯基）] [1,3,4]噻二唑环和/或苯并咪唑环中的氯基会增强抗结核
• Potassium Carbonate-Mediated Green and Efficient Synthesis of Imidazo[2,1-<i>b</i>]-1,3,4-thiadiazoles Using PEG as Solvent
  作者：Mazaahir Kidwai、Divya Bhatnagar、Ritika Chauhan

  DOI：10.1002/jhet.1037

  日期：2013.2

  Polyethylene glycol (PEG) was found to be an inexpensive nontoxic and effective medium for the synthesis of imidazo[2,1-b]-1,3,4-thiadiazoles in the presence of potassium carbonate as a green base in high yields. In addition, the solvent system can be recovered and reused, making this protocol economically and potentially viable.

  聚乙二醇（PEG）被发现是一种廉价的无毒，有效的介质，可在存在下列条件下合成咪唑并[2,1 - b ] -1,3,4-噻二唑。碳酸钾为绿色碱，高产。另外，溶剂系统可以回收和再利用，从而使该方案在经济上和潜在可行。
• Identification of a novel BCL2-specific inhibitor that binds predominantly to the BH1 domain
  作者：Divyaanka Iyer、Supriya V. Vartak、Archita Mishra、Gunaseelan Goldsmith、Sujeet Kumar、Mrinal Srivastava、Mahesh Hegde、Vidya Gopalakrishnan、Mark Glenn、Mahesh Velusamy、Bibha Choudhary、Nagesh Kalakonda、Subhas S. Karki、Avadhesha Surolia、Sathees C. Raghavan

  DOI：10.1111/febs.13815

  日期：2016.9

  The antiapoptotic protein BCL2 is overexpressed in several cancers and contributes to prolonged cell survival and chemoresistance, lending itself as an excellent target for cancer therapy. Here, we report the design, synthesis, and characterization of Disarib, a novel BCL2 inhibitor. Disarib showed selective cytotoxicity in BCL2 high cancer cell lines, and CLL patient primary cells, as compared to BCL2 low cell lines. BCL2 knockdown in cells rendered remarkable resistance to Disarib, while sensitivity was regained upon its ectopic expression, establishing target specificity. In silico, biochemical and biophysical studies demonstrated strong affinity of Disarib to BCL2, but not to other antiapoptotic BCL2 family members viz., BCL‐xL, BCL2A1 etc. Interestingly, biophysical studies showed that BH1 domain deletion mutant demonstrated ~ 67‐fold reduction in BCL2‐Disarib interaction, while it was only ~ 20‐fold in the case of BH3 deletion mutant, suggesting predominant involvement of the BH1 domain for Disarib binding. Thus, we report identification of a novel BCL2 inhibitor with a unique mechanism of BCL2 inhibition, as opposed to the well‐studied BH3 domain targeting.
• Synthesis of Imidazo[2,1-<i>b</i>]-1,3,4-thiadiazoles in DABCO as an Efficient and Recyclable Catalyst
  作者：Kamleshwar Tiwari、Pankaj Kumar Verma、Shyam Babu Singh、Jagdamba Singh

  DOI：10.1080/00397911.2011.574329

  日期：2012.10.15

  An efficient and general method has been described for the synthesis of imidazo[2,1-b]-1,3,4-thiadiazole by the reaction of 2-aminothiadiazoles with phenacyl bromides in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO). The method is suitable for the synthesis of functionalized imidazothiadiazoles.