6-(4-bromo-phenyl)-2-methyl-imidazo[2,1-b][1,3,4]thiadiazole | 37663-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-bromo-phenyl)-2-methyl-imidazo[2,1-b][1,3,4]thiadiazole
• 英文别名: 6-(4-Bromophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole
• CAS: 37663-96-0
• 化学式: C₁₁H₈BrN₃S
• mdl: MFCD00453662
• 分子量: 294.175
• InChiKey: GPFKIFYQAKWUFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  6-(4-bromo-phenyl)-2-methyl-imidazo[2,1-b][1,3,4]thiadiazole 在 哌啶 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Identification of a novel BCL2-specific inhibitor that binds predominantly to the BH1 domain

  摘要：

  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.

  DOI：

  10.1111/febs.13815
• 作为产物：
  描述：

  1-(4-bromo-phenyl)-2-(2-imino-5-methyl-[1,3,4]thiadiazol-3-yl)-ethanone 在 盐酸 作用下， 以 乙二醇乙醚 为溶剂， 反应 6.0h， 以60%的产率得到6-(4-bromo-phenyl)-2-methyl-imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  El-Sherbeny; El-Bendary; El-Subbagh, Bollettino Chimico Farmaceutico, 1997, vol. 136, # 3, p. 253 - 256

  摘要：

  DOI：

文献信息

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

  DOI：——

  日期：——
• PENTIMALLI L.; MILANI G.; BIAVATI F., GAZZ. CHIM. ITAL. <GCIT-A9>, 1975, 105, NO 7-8, 777-787
  作者：PENTIMALLI L.、 MILANI G.、 BIAVATI F.

  DOI：——

  日期：——