5-(5-nitrofuran-2-yl)-N-(prop-2-ynyl)-1,3,4-thiadiazol-2-amine | 1370251-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(5-nitrofuran-2-yl)-N-(prop-2-ynyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-(5-nitrofuran-2-yl)-N-prop-2-ynyl-1,3,4-thiadiazol-2-amine
• CAS: 1370251-34-5
• 化学式: C₉H₆N₄O₃S
• 分子量: 250.238
• InChiKey: NGZDFVWYYKXQFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(5-nitrofuran-2-yl)-N-(prop-2-ynyl)-1,3,4-thiadiazol-2-amine 、 1-(迭氮基甲基)-2-甲苯 在 copper(l) iodide 作用下， 以 水 、 叔丁醇 为溶剂， 生成 N-((1-(2-methylbenzyl)-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
• 作为产物：
  描述：

  5-(5-硝基-2-呋喃基)-1,3,4-噻二唑-2-基胺 在 盐酸 、 铜 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 5-(5-nitrofuran-2-yl)-N-(prop-2-ynyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  New 5-(nitroheteroaryl)-1,3,4-thiadiazols containing acyclic amines at C-2: synthesis and SAR study for their antileishmanial activity

  摘要：

  A novel series of 5-(5-nitrofuran-2-yl)-and 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole-2-amines bearing acyclic amine at C-2 position of thiadiazole ring were synthesized and evaluated in vitro against promastigote and amastigote forms of Leishmania major. The structure-activity of series was investigated by studying 40 compounds. The most active derivatives were hydroxypropylamino-and methoxypropylamino-analogs of 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole (compounds 29 and 32, respectively) with highest selectivity index (SI > 12).

  DOI：

  10.3109/14756366.2012.689297

文献信息

• New 5-(nitroheteroaryl)-1,3,4-thiadiazols containing acyclic amines at C-2: synthesis and SAR study for their antileishmanial activity
  作者：Azar Tahghighi、Saeed Emami、Sepide Razmi、Farzane Rezazade Marznaki、Sussan Kabudanian Ardestani、Siavoush Dastmalchi、Farzad Kobarfard、Abbas Shafiee、Alireza Foroumadi

  DOI：10.3109/14756366.2012.689297

  日期：2013.8.1

  A novel series of 5-(5-nitrofuran-2-yl)-and 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole-2-amines bearing acyclic amine at C-2 position of thiadiazole ring were synthesized and evaluated in vitro against promastigote and amastigote forms of Leishmania major. The structure-activity of series was investigated by studying 40 compounds. The most active derivatives were hydroxypropylamino-and methoxypropylamino-analogs of 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole (compounds 29 and 32, respectively) with highest selectivity index (SI > 12).
• 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.