2-(5-硝基噻吩-2-基)-5-哌嗪-1-基-1,3,4-噻二唑 | 800380-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-(5-硝基噻吩-2-基)-5-哌嗪-1-基-1,3,4-噻二唑
• 英文名称: 1-[5-(5-Nitro-thiophen-2-yl)-[1,3,4]thiadiazol-2-yl]-piperazine
• 英文别名: 1-[5-(5-Nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]piperazine；2-(5-nitrothiophen-2-yl)-5-piperazin-1-yl-1,3,4-thiadiazole
• CAS: 800380-60-3
• 化学式: C₁₀H₁₁N₅O₂S₂
• 分子量: 297.362
• InChiKey: XWVDHOJLARQHDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(5-硝基噻吩-2-基)-5-哌嗪-1-基-1,3,4-噻二唑 、 5-氯-2-酰氯噻吩 在 吡啶 作用下， 以 苯 为溶剂， 以73%的产率得到(5-Chlorothiophen-2-yl)-[4-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]piperazin-1-yl]methanone
  参考文献：
  名称：

  Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines

  摘要：

  The synthesis and anti-leishmanial activity of nitroheteroaryl-1,3,4-thiadiazole- based compounds including 1-[5-(5-nitrofuran2- yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were described. Most of the synthesized compounds exhibited potent anti-leishmanial activity against both promastigote and amastigote forms of Leishmania major at non-cytotoxic concentrations. In general, 5- nitrofuran derivatives were more active than the corresponding 5- nitrothiophene analogues. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.052
• 作为产物：
  描述：

  2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide 在 盐酸 、 ammonium ferric sulfate 、 铜 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 2-(5-硝基噻吩-2-基)-5-哌嗪-1-基-1,3,4-噻二唑
  参考文献：
  名称：

  Synthesis and in vitro leishmanicidal activity of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1,3,4-thiadiazoles

  摘要：

  A series of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1,3,4-thiadiazoles (5a-d and 6a-j) were synthesized and evaluated against Leishmania major promastigotes using H-3-thymidine incorporation. Most of the compounds showed activity better than the reference drug sodium stibogluconate (Pentostam). The most active compound was 6c (IC50 = 0-1 mu M). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.073

文献信息

• Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines
  作者：Mina Behrouzi-Fardmoghadam、Fatemeh Poorrajab、Sussan Kaboudanian Ardestani、Saeed Emami、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.bmc.2008.02.052

  日期：2008.4

  The synthesis and anti-leishmanial activity of nitroheteroaryl-1,3,4-thiadiazole- based compounds including 1-[5-(5-nitrofuran2- yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were described. Most of the synthesized compounds exhibited potent anti-leishmanial activity against both promastigote and amastigote forms of Leishmania major at non-cytotoxic concentrations. In general, 5- nitrofuran derivatives were more active than the corresponding 5- nitrothiophene analogues. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro leishmanicidal activity of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1,3,4-thiadiazoles
  作者：Alireza Foroumadi、Shirin Pournourmohammadi、Fatemeh Soltani、Mitra Asgharian-Rezaee、Shahriar Dabiri、Arsalan Kharazmi、Abbas Shafiee

  DOI：10.1016/j.bmcl.2005.02.073

  日期：2005.4

  A series of 2-(5-nitro-2-furyl) and 2-(5-nitro-2-thienyl)-5-substituted-1,3,4-thiadiazoles (5a-d and 6a-j) were synthesized and evaluated against Leishmania major promastigotes using H-3-thymidine incorporation. Most of the compounds showed activity better than the reference drug sodium stibogluconate (Pentostam). The most active compound was 6c (IC50 = 0-1 mu M). (c) 2005 Elsevier Ltd. All rights reserved.