2-((1-(4-ethoxyphenyl)-1H-1,2,3-triazol-4-yl)methylthio)benzo[d]thiazole | 1362125-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((1-(4-ethoxyphenyl)-1H-1,2,3-triazol-4-yl)methylthio)benzo[d]thiazole
• 英文别名: 2-[[1-(4-Ethoxyphenyl)triazol-4-yl]methylsulfanyl]-1,3-benzothiazole
• CAS: 1362125-20-9
• 化学式: C₁₈H₁₆N₄OS₂
• 分子量: 368.483
• InChiKey: ZEEQJVBCYUFEPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-巯基苯并噻唑 在 copper(ll) sulfate pentahydrate 、 L-ascorbic acid sodium salt 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 7.0h， 生成 2-((1-(4-ethoxyphenyl)-1H-1,2,3-triazol-4-yl)methylthio)benzo[d]thiazole
  参考文献：
  名称：

  Sulfur rich 2-mercaptobenzothiazole and 1,2,3-triazole conjugates as novel antitubercular agents

  摘要：

  A series of benzfused heterocyclic derivatives such as amide conjugates of 2-(benzo[d]thiazol-2-ylthio) acetic acid with aromatic/aliphatic/cyclic secondary amines (5a-5o & 8a-8m); 1,2,3-triazole conjugates of 2-mercaptobenzothiazoles and amide conjugates of indole-3-glyoxalic acid with cyclic secondary amines (14a-14g) have been synthesized and were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. Compounds 8b, 8f, 8g and 8l inhibited the growth of the H37Rv strain at concentrations of 8 mu g/mL. These compounds (8b, 8f, 8g and 8l) have been further identified as bactericidal and are completely killing the microbes at 32-64 mu g/mL concentrations. Molecular docking studies of the active compounds reveal that these compounds are targeting DprE1 and may act as DprE1 inhibitors. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.017

文献信息

• Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities
  作者：Syed Shafi、Mohammad Mahboob Alam、Naveen Mulakayala、Chaitanya Mulakayala、G. Vanaja、Arunasree M. Kalle、Reddanna Pallu、M.S. Alam

  DOI：10.1016/j.ejmech.2012.01.032

  日期：2012.3

  A focused library of novel bis-heterocycles encompassing 2-mercapto benzothiazole and 1,2,3-triazoles were synthesized using click chemistry approach. The synthesized compounds have been tested for their anti-inflammatory activity by using biochemical cyclooxygenase (COX) activity assays and carrageenan-induced hind paw edema. Among the tested compounds, compound 4d demonstrated a potent selective COX-2 inhibition with COX-2/COX-1 ratio of 0.44. Results from carrageenan-induced hind paw edema showed that compounds 4a, 4d, 4e and 4f posses significant anti-inflammatory activity as compared to the standard drug Ibuprofen. The compounds showing significant activity were further subjected to anti-nociceptive activity by writhing test. These four compounds have shown comparable activity with the standard Ibuprofen. Further ulcerogenic studies shows that none of these compounds causing gastric ulceration. (C) 2012 Elsevier Masson SAS. All rights reserved.