3-(4-((benzo[d]thiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)propane-1,2-diol | 1362125-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(4-((benzo[d]thiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)propane-1,2-diol
• 英文别名: 3-[4-(1,3-Benzothiazol-2-ylsulfanylmethyl)triazol-1-yl]propane-1,2-diol
• CAS: 1362125-32-3
• 化学式: C₁₃H₁₄N₄O₂S₂
• 分子量: 322.412
• InChiKey: JFFDPEAKAJSIGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-巯基苯并噻唑 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 9.25h， 生成 3-(4-((benzo[d]thiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)propane-1,2-diol
  参考文献：
  名称：

  Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.01.032

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.