5-(4-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole | 37663-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole
• 英文别名: 6-(4-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole；6-(4-chloro-phenyl)-2-methyl-imidazo[2,1-b][1,3,4]thiadiazole
• CAS: 37663-95-9
• 化学式: C₁₁H₈ClN₃S
• mdl: MFCD00453657
• 分子量: 249.724
• InChiKey: ZSNGKUGMABAGTO-UHFFFAOYSA-N

物化性质

• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：

  5-(4-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole 在 2-碘酰苯甲酸 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 二甲基亚砜 为溶剂， 生成 (E)-1-(6-(4-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of imidazo[2,1-b][1,3,4]thiadiazole–chalcones as apoptosis inducing anticancer agents

  摘要：

  一些咪唑噻二唑 - 查尔酮共轭物的图书馆被合成并研究了其针对各种人类癌细胞系的细胞毒活性。一些经过测试的化合物，如7a、7b、11a和11b，展现了有希望的抗癌活性。

  DOI：

  10.1039/c4md00228h
• 作为产物：
  描述：

  1-(4-chloro-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65%的产率得到5-(4-chlorophenyl)-2-methylimidazo[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

• 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
• 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.
• One-pot synthesis of new triazole—Imidazo[2,1-b][1,3,4]thiadiazole hybrids via click chemistry and evaluation of their antitubercular activity
  作者：Jurupula Ramprasad、Nagabhushana Nayak、Udayakumar Dalimba、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2015.08.009

  日期：2015.10

  A new series of triazole-imidazo[2,1-b][1,3,4]thiadiazole hybrids (6a-s, 7a) were designed by a molecular hybridisation approach and the target molecules were synthesized via one pot click chemistry protocol. All the intermediates and final molecules were characterised using spectral methods and one of the target compounds (6c) was analysed by the single crystal XRD study. The derivatives were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain. Two compounds, 6f and 6n, demonstrated significant growth inhibitory activity against the bacterial strain with a MIC of 3.125 mu g/mL. The presence of chloro substituent on the imidazo[2,1-b][1,3,4]thiadiazole ring and ethyl, benzyl or cyanomethylene groups on the 1,2,3-triazole ring enhance the inhibition activity of the molecules. The active compounds are not toxic to a normal cell line which signifies the lack of general cellular toxicity of these compounds. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of imidazo[2,1-b][1,3,4]thiadiazole–chalcones as apoptosis inducing anticancer agents
  作者：Ahmed Kamal、Vangala Santhosh Reddy、Karnewar Santosh、G. Bharath Kumar、Anver Basha Shaik、Rasala Mahesh、Sumit. S. Chourasiya、Ibrahim Bin Sayeed、Srigiridhar Kotamraju

  DOI：10.1039/c4md00228h

  日期：——

  A library of imidazothiadiazole–chalcone conjugates were synthesised and investigated for their cytotoxic activity against various human cancer cell lines. Some of the tested compounds like7a,7b,11aand11bexhibited promising anticancer activity.

  一些咪唑噻二唑 - 查尔酮共轭物的图书馆被合成并研究了其针对各种人类癌细胞系的细胞毒活性。一些经过测试的化合物，如7a、7b、11a和11b，展现了有希望的抗癌活性。