2-sulfamoyl-5-(4'-methoxyphenyl)-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole

• 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-sulfamoyl-5-(4'-methoxyphenyl)-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole
• 英文别名: 5-(4-Methoxyphenyl)-6-phenyl-imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamide；5-(4-methoxyphenyl)-6-phenylimidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamide
• 化学式: C₁₇H₁₄N₄O₃S₂
• 分子量: 386.455
• InChiKey: BCMJUVLSEBENTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)-1-苯基乙酮 在 四磷十氧化物 、 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 2-sulfamoyl-5-(4'-methoxyphenyl)-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis, spectral studies and biological evaluation of a novel series of 2-substituted-5,6-diarylsubstituted imidazo(2,1-b)-1,3,4-thiadiazole derivatives as possible anti-tubercular agents

  摘要：

  A novel series of 18 analogs of 2-substituted-5,6-diarylsubstituted imidazo(2,1-b)-1,3,4-thiadiazole 6a-r have been synthesized by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles 5a-d and an appropriately substituted alpha-bromo-1,2-(p-substituted)diaryl-1-ethanones 4a-e. Structures of these compounds were established by physiochemical, elemental analysis and spectral data. All the title compounds were tested for their in-vitro anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv using Alamar Blue susceptibility test and the activity expressed as the minimum inhibitory concentration (MIC) in mu g/ml. Among synthesized compounds, compound 6h (MIC = 1.25 mu g/ml) exhibited excellent anti-tubercular activity with respect to other synthesized compounds and reference drugs. Compounds 6c, 6f, and 6g have also displayed an encouraging anti-tubercular activity profile. Further, some title compounds were also assessed for their cytotoxic activity (IC50) against in a mammalian Vero cell line using MTT assay. The results reveal that these compounds exhibit anti-tubercular activity at non-cytotoxic concentrations.

  DOI：

  10.1007/s00044-011-9646-9

文献信息

• Synthesis and biological evaluation of 2-trifluoromethyl/sulfonamido-5,6-diaryl substituted imidazo[2,1-b]-1,3,4-thiadiazoles: A novel class of cyclooxygenase-2 inhibitors
  作者：Andanappa K. Gadad、Mahesh B. Palkar、K. Anand、Malleshappa N. Noolvi、Thippeswamy S. Boreddy、J. Wagwade

  DOI：10.1016/j.bmc.2007.09.038

  日期：2008.1

  A series of 2-trifluoromethyl/sulfonamido-5,6-diaryl substituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives 15a-j have been synthesized by the reaction of 2-amino-5-trifluoromethyl/sulfonamido-1,3,4-thiadiazoles 14a-b and appropriately substituted alpha-bromo-1,2-(p-substituted)diaryl-l-ethanones 13a-h. Structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass, and HRMS data. The selected compounds were evaluated for their preliminary in vitro cyclooxygenase inhibitory activity against COX-2 and COX-lenzymes using colorimetric method. The compounds tested showed selective inhibitory activity toward COX-2 (80.6-49.4%) over COX-1 (30.6-8.6), amongst them compounds 15f and 15j showed appreciable COX-2 selective inhibitory activity. These compounds also exhibited significant anti-inflammatory activity (70.09-42.32%), which is comparable to that of celecoxib in the carrageenan-induced rat paw edema method. (c) 2007 Elsevier Ltd. All rights reserved.