N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine | 1370251-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine
• 英文别名: N-[(1-benzyltriazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine
• CAS: 1370251-35-6
• 化学式: C₁₆H₁₃N₇O₃S
• 分子量: 383.39
• InChiKey: DBPANULQXARIFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-chloro-5-(5-nitro-2-furyl)-1,3,4-thiadiazole 在 copper(l) iodide 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis and anti-leishmanial activity of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines containing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moieties

  摘要：

  A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of thiadiazole ring via click chemistry. The title compounds namely, N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines (3a-n) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major. Most compounds exhibited good anti-leishmanial activity against the promastigote form of L major. The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i, which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.046

文献信息

• Synthesis and anti-leishmanial activity of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines containing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moieties
  作者：Azar Tahghighi、Sepideh Razmi、Mohammad Mahdavi、Parham Foroumadi、Sussan K. Ardestani、Saeed Emami、Farzad Kobarfard、Siavoush Dastmalchi、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2012.01.046

  日期：2012.4

  A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of thiadiazole ring via click chemistry. The title compounds namely, N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines (3a-n) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major. Most compounds exhibited good anti-leishmanial activity against the promastigote form of L major. The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i, which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index. (C) 2012 Elsevier Masson SAS. All rights reserved.