N-(4-(dibenzo[b,d]furan-2-yl)thiazol-2-yl)-2-(4-(4-pentylphenyl)-1H-1,2, 3-triazol-1-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-(4-(dibenzo[b,d]furan-2-yl)thiazol-2-yl)-2-(4-(4-pentylphenyl)-1H-1,2, 3-triazol-1-yl)acetamide
• 英文别名: N-(4-dibenzofuran-2-yl-1,3-thiazol-2-yl)-2-[4-(4-pentylphenyl)triazol-1-yl]acetamide
• 化学式: C₃₀H₂₇N₅O₂S
• 分子量: 521.643
• InChiKey: XOUCOJOECXRGME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-二苯并呋喃)乙酮 在 吡啶 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 碘 、 sodium ascorbate 、 sodium iodide 、 copper(II) oxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 12.0h， 生成 N-(4-(dibenzo[b,d]furan-2-yl)thiazol-2-yl)-2-(4-(4-pentylphenyl)-1H-1,2, 3-triazol-1-yl)acetamide
  参考文献：
  名称：

  Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides

  摘要：

  A series of novel dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides, designed by assembling antitubercular pharmacophoric fragments, dibenzofuran, 2-aminothiazole and substituted triazoles in one molecular architecture, were evaluated against Mycobacterium tuberculosis. The new analogues 6a-p accomplished in four step synthetic sequence utilizing click chemistry in the penultimate step, was fully characterized by their NMR and mass spectral data. Among the compounds 6a-p screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, three compounds 6j (MIC: 1.56 mu g/mL); 6a and 6p (MIC: 3.13 mu g/mL) was found to be most active and exhibited lower cytotoxicity. Among these three, 6j could be a candidate to consider as a drug like hit analogue for further development. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.05.085

文献信息

• Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides
  作者：Goverdhan Surineni、Perumal Yogeeswari、Dharmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bmcl.2016.05.085

  日期：2016.8

  A series of novel dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides, designed by assembling antitubercular pharmacophoric fragments, dibenzofuran, 2-aminothiazole and substituted triazoles in one molecular architecture, were evaluated against Mycobacterium tuberculosis. The new analogues 6a-p accomplished in four step synthetic sequence utilizing click chemistry in the penultimate step, was fully characterized by their NMR and mass spectral data. Among the compounds 6a-p screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv, three compounds 6j (MIC: 1.56 mu g/mL); 6a and 6p (MIC: 3.13 mu g/mL) was found to be most active and exhibited lower cytotoxicity. Among these three, 6j could be a candidate to consider as a drug like hit analogue for further development. (C) 2016 Elsevier Ltd. All rights reserved.