4-(4-methoxyphenyl)-1-[(4-nitroimidazol-1-yl)acetyl]thiosemicarbazide | 1186048-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-methoxyphenyl)-1-[(4-nitroimidazol-1-yl)acetyl]thiosemicarbazide
• 英文别名: 1-(4-Methoxyphenyl)-3-[[2-(4-nitroimidazol-1-yl)acetyl]amino]thiourea
• CAS: 1186048-61-2
• 化学式: C₁₃H₁₄N₆O₄S
• 分子量: 350.358
• InChiKey: PYXKIIFVASOINW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-1-[(4-nitroimidazol-1-yl)acetyl]thiosemicarbazide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以80%的产率得到4-(4-methoxyphenyl)-3-[(4-nitroimidazol-1-yl)methyl]-1,2,4-triazoline-5-thione
  参考文献：
  名称：

  New Derivatives of Thiosemicarbazide and 1,2,4-Triazoline-5-thione with Potential Antimicrobial Activity

  摘要：

  In the reaction of the hydrazide of (4-nitroimidazol-1-yl)acetic acid 1 with isothiocyanates, the respective thiosemicarbazide derivatives 2-6 were obtained. Further cyclization with 2% NaOH led to the formation of 3-[(4-nitroimidazol-1-yl)-methyl]-4-substituted-1,2,4-triazoline-5-thiones 7-11. The structures of all new products were confirmed by analytical and spectroscopic methods. Six compounds 2-5, 8, and 10 were screened for their in vitro activity against some species of aerobic bacteria and fungi. Compound 3 appears to be a promising precursor of agents with antibacterial activity against Micrococcus luteus.

  DOI：

  10.1080/10426500802208490
• 作为产物：
  描述：

  2-(4-硝基咪唑-1-基)乙酸乙酯 在 一水合肼 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 4-(4-methoxyphenyl)-1-[(4-nitroimidazol-1-yl)acetyl]thiosemicarbazide
  参考文献：
  名称：

  Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles

  摘要：

  制备了一系列[(4-硝基-1H-咪唑-1-基)甲基]-1,2,4-三唑和 1,3,4-噻二唑，并评估了它们对敏感和耐药幽门螺杆菌菌株的活性。 对这些系列化合物结构-活性关系的研究表明，硝基咪唑分子的类型和杂芳基类似物上的悬垂基团对抗幽门螺杆菌活性有显著影响。 在三唑系列中，三唑环上含有 4-甲基苯基的化合物 5d 是对甲硝唑敏感菌株和耐药菌株抗性最强的化合物，浓度为 8 \mu g。

  DOI：

  10.3906/kim-1004-522

文献信息

• New Derivatives of Thiosemicarbazide and 1,2,4-Triazoline-5-thione with Potential Antimicrobial Activity
  作者：Monika Wujec、Urszula Kosikowska、Agata Siwek、Anna Malm

  DOI：10.1080/10426500802208490

  日期：2009.3.10

  In the reaction of the hydrazide of (4-nitroimidazol-1-yl)acetic acid 1 with isothiocyanates, the respective thiosemicarbazide derivatives 2-6 were obtained. Further cyclization with 2% NaOH led to the formation of 3-[(4-nitroimidazol-1-yl)-methyl]-4-substituted-1,2,4-triazoline-5-thiones 7-11. The structures of all new products were confirmed by analytical and spectroscopic methods. Six compounds 2-5, 8, and 10 were screened for their in vitro activity against some species of aerobic bacteria and fungi. Compound 3 appears to be a promising precursor of agents with antibacterial activity against Micrococcus luteus.
• Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles
  作者：ASAL FALLAH-TAFTI、TAHMINEH AKBARZADEH、PARASTOO SANIEE、FARIDEH SIAVOSHI、ABBAS SHAFIEE、ALIREZA FOROUMADI

  DOI：10.3906/kim-1004-522

  日期：——

  A series of [(4-nitro-1H-imidazol-1-yl)methyl]-1,2,4- triazoles and 1,3,4-thiadiazoles were prepared and evaluated for their activity against sensitive and resistant H. pylori strains. Study of the structure-activity relationship of these series of compounds indicated that the type of nitroimidazole moiety and the pendent group on the heteroaryl analog dramatically impact the anti-H. pylori activity. In triazole series, compound 5d, containing a 4-methyl phenyl group on the triazole ring, was the most potent compound tested against both metronidazole-sensitive and -resistant strains at a concentration of 8 \mu g.

  制备了一系列[(4-硝基-1H-咪唑-1-基)甲基]-1,2,4-三唑和 1,3,4-噻二唑，并评估了它们对敏感和耐药幽门螺杆菌菌株的活性。 对这些系列化合物结构-活性关系的研究表明，硝基咪唑分子的类型和杂芳基类似物上的悬垂基团对抗幽门螺杆菌活性有显著影响。 在三唑系列中，三唑环上含有 4-甲基苯基的化合物 5d 是对甲硝唑敏感菌株和耐药菌株抗性最强的化合物，浓度为 8 \mu g。