1-(5-bromo-2-thienylcarbonyl)-4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]piperazine | 1148109-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(5-bromo-2-thienylcarbonyl)-4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]piperazine
• 英文别名: (5-Bromothiophen-2-yl)-[4-[5-(1-methyl-5-nitroimidazol-2-yl)-1,3,4-thiadiazol-2-yl]piperazin-1-yl]methanone
• CAS: 1148109-21-0
• 化学式: C₁₅H₁₄BrN₇O₃S₂
• 分子量: 484.357
• InChiKey: XPSAHFKYHHPNHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-溴噻吩-2-羰酰氯 、 2-<2-(1-Piperazinyl-5-thiadiazolyl>-1-methyl-5-nitroimidazol 在 吡啶 作用下， 以 苯 为溶剂， 反应 72.0h， 以77%的产率得到1-(5-bromo-2-thienylcarbonyl)-4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]piperazine
  参考文献：
  名称：

  Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: Synthesis and in vitro biological evaluation

  摘要：

  A series of 1-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were synthesized and evaluated in vitro against Leishmania major. Most of the target compounds exhibited good anti-leishmanial activity against the promastigote form of L. major at non-cytotoxic concentrations. The most active compound was 1-[(5-chloro-2-thienyl)carbonyl]-4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)1,3,4-thiadiazol-2-y]piperazine (5f) with an IC50 value of 9.35 +/- 0.67 mu M against L. major promastigotes. In addition, this compound was effective against intracellular L. major and significantly decreased the infectivity index. (c) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.039

文献信息

• Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: Synthesis and in vitro biological evaluation
  作者：Fatemeh Poorrajab、Sussan Kabudanian Ardestani、Saeed Emami、Mina Behrouzi-Fardmoghadam、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2008.03.039

  日期：2009.4

  A series of 1-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were synthesized and evaluated in vitro against Leishmania major. Most of the target compounds exhibited good anti-leishmanial activity against the promastigote form of L. major at non-cytotoxic concentrations. The most active compound was 1-[(5-chloro-2-thienyl)carbonyl]-4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)1,3,4-thiadiazol-2-y]piperazine (5f) with an IC50 value of 9.35 +/- 0.67 mu M against L. major promastigotes. In addition, this compound was effective against intracellular L. major and significantly decreased the infectivity index. (c) 2008 Elsevier Masson SAS. All fights reserved.