[5-(1-Methyl-5-nitro-1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-hydrazine | 823200-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [5-(1-Methyl-5-nitro-1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-hydrazine
• CAS: 823200-60-8
• 化学式: C₆H₇N₇O₂S
• 分子量: 241.233
• InChiKey: PWARXBYDSUULCK-UHFFFAOYSA-N

物化性质

• 沸点：
  497.1±37.0 °C(Predicted)
• 密度：
  2.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  124.79
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-硝基香兰素 、 [5-(1-Methyl-5-nitro-1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-hydrazine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以93%的产率得到2-methoxy-4-[(E)-[[5-(1-methyl-5-nitroimidazol-2-yl)-1,3,4-thiadiazol-2-yl]hydrazinylidene]methyl]-6-nitrophenol
  参考文献：
  名称：

  Studies toward the structural optimization of new brazilizone-related trypanocidal 1,3,4-thiadiazole-2-arylhydrazone derivatives

  摘要：

  Megazol is a highly active compound against Trypanosoma cruzi, and has become a core structure for the design of new trypanocidal agents. Recently, we have identified the new potent trypanocide agent Brazilizone A, which presents an IC50 twofold more potent than the prototype megazol. This result has encouraged us to further explore structurally-related 1,3,4-thiadiazole-2-arylhydrazone derivatives, in order to get a better understanding of their structural and antiprotozoal activity relationships. Herein we report the synthesis and trypanocidal profile of thirteen new Brazilizone A analogues, which supported the construction of 3D-QSAR models used for its structural optimization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.027
• 作为产物：
  描述：

  5-(1-甲基-5-硝基-1H-咪唑-2-基)-1,3,4-噻二唑-2-胺 在 盐酸 、 铜 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 [5-(1-Methyl-5-nitro-1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-hydrazine
  参考文献：
  名称：

  Synthesis and antitrypanosomal profile of new functionalized 1,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues

  摘要：

  In this work we reported the synthesis and the trypanocidal profile of new 1,3,4-thiadiazole-2-arylhydrazone derivatives of nitroimidazole series (4) or phenyl series (5), designed by exploring the molecular hybridization approach between megazol (2) and guanyl hydrazone derivative (3). The evaluation of the activity against bloodstream trypomastigote forms of Trypanosoma cruzi forms lead us to identify a new potent trypamomicide prototype, that is, brazilizone A (4k), which present an IC50/24h = 5.3 muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.007