6-(4-bromophenyl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole | 1044282-60-1

• 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-bromophenyl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• 英文别名: 6-(4-Bromophenyl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
• CAS: 1044282-60-1
• 化学式: C₁₇H₁₂BrN₃OS
• 分子量: 386.272
• InChiKey: SXSCGQWQCPZQPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-bromophenyl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 3-(5-(4-bromophenyl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Novel imidazo[2,1-b]-1,3,4-thiadiazoles as promising antifungal agents against clinical isolate of Cryptococcus neoformans

  摘要：

  We herein report the synthesis and in vitro antimicrobial evaluation of twenty five novel hybrid derivatives of imidazo [2,1-b]-1,3,4-thiadiazole containing chalcones (5a-o) and Schiff bases (6a-j) against three fungal strains (Candida albicans, Cryptococcus neoformans and Asperg-illus niger). Most of the tested compounds displayed substantial anti-fungal activity with MICs ranging between 1.56 and 100 mu g/mL. Compounds 5a, 5b and 5n exhibited promising activity against C neoformans at a MIC 1.56 mu g/mL. In addition, compound 5n also demonstrated significant antifungal activity against the clinical isolates of C neoformans at MIC 3.125 mu g/mL. However, moderate activity was observed for these compounds against four bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) and Mycobacterium tuberculosis (H(37)Rv). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.021
• 作为产物：
  描述：

  大茴香酸 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 6-(4-bromophenyl)-2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  杂环 48. 咪唑并[2,1-b][1,3,4]噻二唑衍生物作为抗炎剂的合成、表征和生物学评价。

  摘要：

  非甾体抗炎药（NSAID）是一类重要的药理学药物，用于治疗炎症性疾病。它们还具有严重的副作用，例如胃肠道损伤、心血管风险增加和肾功能异常。为了合成副作用更安全的新型抗炎镇痛化合物，合成了一系列2,6-二芳基咪唑并[2,1-b][1,3,4]噻二唑衍生物5a⁻l并在体内评估了它们对角叉菜胶引起的大鼠爪水肿的抗炎和镇痛活性。在所有化合物中，与标准药物双氯芬酸相比，5c 显示出更好的抗炎活性，而化合物 5g、5i、5j 则表现出与双氯芬酸相当的抗伤害活性。这些化合物均未表现出致溃疡活性。进行了分子对接研究，以研究化合物与靶标环氧合酶 (COX-1/COX-2) 之间的理论键相互作用。与双氯芬酸相比，化合物5c表现出更高的COX-2抑制作用。

  DOI：

  10.3390/molecules23102425

文献信息

• 2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazoles: Search for anticancer agents
  作者：Malleshappa N. Noolvi、Harun M. Patel、Sarita Kamboj、Amandeep Kaur、Vikas Mann

  DOI：10.1016/j.ejmech.2012.08.012

  日期：2012.10

  In this study, some novel 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles 4 (a-i), 7 (a-p) and 11 (a-i) were synthesized from 5-substituted-1,3,4-thiadiazol-2-amine. The newly synthesized compounds 4a, 4b, 4c, 4e, 4g, 7j, 7l, 11b and 11c were evaluated in the National Cancer Institute for single dose in vitro primary cytotoxicity assay. Among the tested nine compounds, compound 4b (107166/760239) and 4c (107168/760240) were passed the criteria for activity in this assay and scheduled automatically for evaluation against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. 3-(2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)aniline (4c) exhibited significant in vitro anticancer activity against Non Small Cell Lung Cancer HOP-92 cell line (GI(50): 0.114 mu M) and Renal Cancer CAKI-1 cell line (GI(50): 0.743 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.