4-amino-5-(thiophen-2-yl-methyl)-2,4-dihydro-1,2,4-triazol-3-one | 878560-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-5-(thiophen-2-yl-methyl)-2,4-dihydro-1,2,4-triazol-3-one
• 英文别名: 4-amino-3-(2-thienylmethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one；4-amino-5-(2-thienylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one；4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one；4-Amino-5-[(thiophen-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one；4-amino-3-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5-one
• CAS: 878560-24-8
• 化学式: C₇H₈N₄OS
• 分子量: 196.233
• InChiKey: GKLUGRQYYONCAW-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C(Solv: water (7732-18-5))
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-5-(thiophen-2-yl-methyl)-2,4-dihydro-1,2,4-triazol-3-one 在 乙醇 、 sodium 、 一水合肼 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 18.0h， 生成 1-(2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-triazole-1-yl)acetyl)-4-phenylthiosemicarbazide
  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：

  N'-1-ethoxy-2-thiophen-2-yl-ethylydene hydrazino carboxylic acid ethyl ester 在 一水合肼 作用下， 以 水 为溶剂， 反应 8.0h， 生成 4-amino-5-(thiophen-2-yl-methyl)-2,4-dihydro-1,2,4-triazol-3-one
  参考文献：
  名称：

  Influence of functional group effect on the K-shell X-ray production cross-sections and average fluorescence yields of sulphur in 1,2,4-triazol-5-one compounds containing thiophene

  摘要：

  The influence of the inductive and mesomeric effects on the K X-ray production cross-sections (sigma(K alpha beta)) and average fluorescence yields ((omega) over bar (K alpha beta)) of sulphur atoms in aromatic thiophene ring was investigated. The samples were excited by 5.96 keV photons from a Fe-55 annular radioactive source. K X-rays emitted by samples were counted by an Ultra-LEGe detector with a resolution of 150 eV at 5.96 keV. It was observed the effects of the changing the number of CH2 groups bound to N-4 at position of 1,2,4-triazol-5-one on the K X-ray production cross-sections (sigma(K alpha beta))and average fluorescence yields ((omega) over bar (K alpha beta)) of sulphur in aromatic thiophene ring. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.cplett.2008.07.010

文献信息

• Synthesis and characterisations of some new 2,4-dihydro-[1,2,4]- triazol-3-one derivatives and X-ray crystal structures of 4-(3-phenylallylideneamino)-5-thiophen-2-yl-methyl-2,4-dihydro-[1,2,4]triazol-3-one
  作者：KEMAL SANCAK、YASEMİN ÜNVER、CANAN KAZAK、ESRA DÜĞDÜ、BURCU ARSLAN

  DOI：10.3906/kim-0905-1

  日期：——

  Compounds 2 were synthesised via the reaction of 4-amino-5-thiophen-2-yl-methyl-2,4-dihydro-[1,2,4]-triazol-3-one (1) with aldehydes. Compounds 3 and 4 were obtained from compounds 2 with bromo acetophenone and ethyl bromoacetate, respectively. The synthesis of compounds 2, 3, and 4 and crystal structure of compound 2a are being reported. The molecular structures were identified by IR, ^1H-NMR, ^13}C-NMR, MS, and elemental analyses. Compound 2a crystallises in the monoclinic P 2_1/n space group, with a = 6.565(5) Å, b = 18.278(5) Å, c = 13.8166(18) Å, \beta = 96.227(5)°, V = 1553.6(14) Å^3, Z = 4. The newly compounds synthesised were screened for their antibacterial and antifungal properties. Among the compounds, 4d showed antimicrobial activity against Candida albicans ATCC 60193 and Candida tropicalis ATCC 13803.

  化合物2是通过4-氨基-5-噻吩-2-基-甲基-2,4-二氢-[1,2,4]-三唑-3-酮(1)与醛反应合成的。 化合物3和4分别由化合物2与溴苯乙酮和溴乙酸乙酯反应得到。 化合物2、3和4的合成以及化合物2a的晶体结构正在报道中。 通过IR、^1H-NMR、^13}C-NMR、MS和元素分析鉴定了分子结构。 化合物2a结晶于单斜晶系P 2_1/n 空间群，a = 6.565(5) Å, b = 18.278(5) Å, c = 13.8166(18) Å, β = 96.227(5)°, V = 1553.6 (14) Å^3, Z = 4。筛选新合成的化合物的抗菌和抗真菌特性。 在这些化合物中，4d 对白色念珠菌 ATCC 60193 和热带念珠菌 ATCC 13803 显示出抗菌活性。
• Microwave-assisted synthesis and characterization and theoretical calculations of the first example of free and metallophthalocyanines from salen type Schiff base derivative bearing thiophen and triazole heterocyclic rings
  作者：Kerim Serbest、İsmail Değirmencioğlu、Yasemin Ünver、Mustafa Er、Cihan Kantar、Kemal Sancak

  DOI：10.1016/j.jorganchem.2007.09.026

  日期：2007.12

  conditions and the products purified by several techniques. The newly prepared compounds have been characterized by elemental analyses, IR, 1H NMR, MS and UV–Vis spectroscopy. Furthermore, theoretical calculations of metallophthalocyanines CuPc, NiPc, ZnPc and CoPc were carried out to comparatively describe the molecular structures, molecular orbital and UV–Vis spectra of metallophthalocyanine complexes

  Co，Ni，Cu和Zn的新型无金属和金属酞菁配合物是通过暴露于微波辐射和回流条件下合成的，并通过多种技术对产物进行纯化。新制备的化合物已通过元素分析IR（1）进行了表征1 H NMR，MS和UV-Vis光谱。此外，进行了金属酞菁CuPc，NiPc，ZnPc和CoPc的理论计算，以根据HF理论比较描述了金属酞菁配合物的分子结构，分子轨道和UV-Vis光谱。比较了不同分子的几何形状，分子轨道。中心孔尺寸的模拟顺序为CoPc> NiPc NiPc> ZnPc> CuPc的顺序变化。金属酞菁配合物的计算结构，电子吸收光谱与实验结果具有很好的一致性。
• Influence of functional group effect on the K-shell X-ray production cross-sections and average fluorescence yields of sulphur in 1,2,4-triazol-5-one compounds containing thiophene
  作者：V. Aylıkcı、E. Cengiz、G. Apaydın、Y. Ünver、K. Sancak、E. Tıraşoğlu

  DOI：10.1016/j.cplett.2008.07.010

  日期：2008.8

  The influence of the inductive and mesomeric effects on the K X-ray production cross-sections (sigma(K alpha beta)) and average fluorescence yields ((omega) over bar (K alpha beta)) of sulphur atoms in aromatic thiophene ring was investigated. The samples were excited by 5.96 keV photons from a Fe-55 annular radioactive source. K X-rays emitted by samples were counted by an Ultra-LEGe detector with a resolution of 150 eV at 5.96 keV. It was observed the effects of the changing the number of CH2 groups bound to N-4 at position of 1,2,4-triazol-5-one on the K X-ray production cross-sections (sigma(K alpha beta))and average fluorescence yields ((omega) over bar (K alpha beta)) of sulphur in aromatic thiophene ring. (C) 2008 Elsevier B. V. All rights reserved.
• New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazole–thiols
  作者：Yasemin Ünver、Kemal Sancak、Fatih Çelik、Emrah Birinci、Murat Küçük、Serkan Soylu、Nesibe Arslan Burnaz

  DOI：10.1016/j.ejmech.2014.01.014

  日期：2014.9

  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.