2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)acetohydrazide | 1620997-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)acetohydrazide
• 英文别名: 2-[4-Amino-5-oxo-3-(thiophen-2-ylmethyl)-1,2,4-triazol-1-yl]acetohydrazide；2-[4-amino-5-oxo-3-(thiophen-2-ylmethyl)-1,2,4-triazol-1-yl]acetohydrazide
• CAS: 1620997-47-8
• 化学式: C₉H₁₂N₆O₂S
• 分子量: 268.299
• InChiKey: ZZXBTWRULQPAPF-UHFFFAOYSA-N

物化性质

• 熔点：
  196-197 °C
• 密度：
  1.74±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)acetohydrazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 4-amino-2-((4-(4-fluorophenyl)-5-mercapto-4H-1,2,4-triazole-3-yl)methyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one
  参考文献：
  名称：

  New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazole–thiols

  摘要：

  Key compound 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohydrazide (3) was synthesized by reacting hydrazine hydrate with ethyl-2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1yl)acetate (2), obtained in basic media from 4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (1). Compound 3 was converted to thiosemicarbazide derivatives (4a-d) and Schiff base derivatives 6a-e and 7a-e. The treatment of compound 4 with NaOH gave 4-amino-2-((4-(4-aryl)-5-mercapto-4H-1,2,4-triazole-3-yl)methyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-ones (5a-d). All newly compounds, well characterized by elemental analyses, IR, (1)H NMR, (13)C NMR and mass spectral studies were tested for their antioxidant and antimicrobial activities. Thiosemicarbazide derivatives (4a-d) were highly active in two antioxidant tests with 69.0-88.2% DPPH· scavenging and 503-1257 μM TEAC values, while the others showed lower or no activity. The results of the two antioxidant tests correlated well. Moreover, Thiosemicarbazide derivatives (4a-d) also showed antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Mycobacterium smegmatis. Thiosemicarbazide group deserves attention in the synthesis of bioactive compounds.

  DOI：

  10.1016/j.ejmech.2014.01.014
• 作为产物：
  描述：

  ethyl 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)acetate 在 一水合肼 作用下， 以 正丁醇 为溶剂， 反应 6.0h， 以85.5%的产率得到2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)acetohydrazide
  参考文献：
  名称：

  New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazole–thiols

  摘要：

  Key compound 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohydrazide (3) was synthesized by reacting hydrazine hydrate with ethyl-2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1yl)acetate (2), obtained in basic media from 4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (1). Compound 3 was converted to thiosemicarbazide derivatives (4a-d) and Schiff base derivatives 6a-e and 7a-e. The treatment of compound 4 with NaOH gave 4-amino-2-((4-(4-aryl)-5-mercapto-4H-1,2,4-triazole-3-yl)methyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-ones (5a-d). All newly compounds, well characterized by elemental analyses, IR, (1)H NMR, (13)C NMR and mass spectral studies were tested for their antioxidant and antimicrobial activities. Thiosemicarbazide derivatives (4a-d) were highly active in two antioxidant tests with 69.0-88.2% DPPH· scavenging and 503-1257 μM TEAC values, while the others showed lower or no activity. The results of the two antioxidant tests correlated well. Moreover, Thiosemicarbazide derivatives (4a-d) also showed antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Mycobacterium smegmatis. Thiosemicarbazide group deserves attention in the synthesis of bioactive compounds.

  DOI：

  10.1016/j.ejmech.2014.01.014

文献信息

• Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities
  作者：Yasemin Ünver、Sadik Deniz、Fatih Çelik、Zeynep Akar、Murat Küçük、Kemal Sancak

  DOI：10.1080/14756366.2016.1206088

  日期：2016.11.3

  (3) was the most active, and the effect of the substituent type of the thiophene ring on the activity was same for both Schiff bases (4a-d) and Mannich bases (5a-d). Among the newly synthesized triazole derivatives, the Schiff base 4d and the Mannich base 5d carrying nitro substituent on the thiophene ring showed promising antibacterial and antifungal activity, with lower MIC values than the standard

  通过使CS 2 / KOH与化合物1反应来合成化合物2。用水合肼处理化合物2产生了化合物3。然后，通过与几种芳族醛的处理将化合物3转化为席夫碱（4a-d）。用吗啉处理含有席夫碱的三唑化合物4a-d，得到化合物5a-d。测试所有化合物的抗氧化和抗菌活性。DPPH•自由基清除和三价铁还原/抗氧化能力方法的抗氧化剂测试结果显示出良好的抗氧化剂活性。三唑-硫醇（3）活性最高，噻吩环的取代基类型对活性的影响对于席夫碱（4a-d）和曼尼希碱（5a-d）都是相同的。在新合成的三唑衍生物中，