4-amino-5-[2-(4-hydroxyphenyl)ethyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione | 1083196-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-amino-5-[2-(4-hydroxyphenyl)ethyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-amino-5-(2-(4-hydroxyphenyl)ethyl)-2,4-dihydro-3H-1,2,4-triazol-3-thione；4-Amino-5-[2-(4-hydroxyphenyl)ethyl]-2,4-dihydro-3h-1,2,4-triazol-3-thione；4-amino-3-[2-(4-hydroxyphenyl)ethyl]-1H-1,2,4-triazole-5-thione
• CAS: 1083196-18-2
• 化学式: C₁₀H₁₂N₄OS
• 分子量: 236.297
• InChiKey: DBOKFTZEJDNUBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-5-[2-(4-hydroxyphenyl)ethyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 、 2-溴-4'-硝基苯乙酮 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到3-[2-(4-hydroxyphenyl)ethyl]-6-(4-nitrophenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine
  参考文献：
  名称：

  新的三唑并噻二嗪衍生物的合成及其抗生活性

  摘要：

  通过4-氨基-5-取代的2,4-二氢-3H-1,2,4-三唑-3-硫酮与苯甲酰基溴的闭环反应合成了新的三唑并二嗪衍生物。该化合物在体外针对各种念珠菌进行了测试，并与酮康唑进行了比较。在这些化合物中，发现在三唑并噻二嗪环（2i）上带有环己基部分和对氯苯基取代基的化合物是对抗白色念珠菌的最有效衍生物（ATCC 90028）。很显然，有抗念珠菌活性和两个官能部分，即脂环族基团和之间的正相关p三唑并噻二嗪环上的-氯苯基取代基。还使用MTT测定法研究了这些化合物的细胞毒性作用。化合物2a显示出最高的细胞毒性活性，而化合物2f显示出对NIH / 3T3细胞的最低细胞毒性活性。

  DOI：

  10.1016/j.ejmech.2011.09.020
• 作为产物：
  描述：

  对羟基苯丙酸 、 硫代卡巴肼 反应 2.0h， 生成 4-amino-5-[2-(4-hydroxyphenyl)ethyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  新的三唑并噻二嗪衍生物的合成及其抗生活性

  摘要：

  通过4-氨基-5-取代的2,4-二氢-3H-1,2,4-三唑-3-硫酮与苯甲酰基溴的闭环反应合成了新的三唑并二嗪衍生物。该化合物在体外针对各种念珠菌进行了测试，并与酮康唑进行了比较。在这些化合物中，发现在三唑并噻二嗪环（2i）上带有环己基部分和对氯苯基取代基的化合物是对抗白色念珠菌的最有效衍生物（ATCC 90028）。很显然，有抗念珠菌活性和两个官能部分，即脂环族基团和之间的正相关p三唑并噻二嗪环上的-氯苯基取代基。还使用MTT测定法研究了这些化合物的细胞毒性作用。化合物2a显示出最高的细胞毒性活性，而化合物2f显示出对NIH / 3T3细胞的最低细胞毒性活性。

  DOI：

  10.1016/j.ejmech.2011.09.020

文献信息

• New pyrazoline derivatives and their antidepressant activity
  作者：Zafer Asım Kaplancıklı、Ahmet Özdemir、Gülhan Turan-Zitouni、Mehlika Dilek Altıntop、Özgür Devrim Can

  DOI：10.1016/j.ejmech.2010.06.011

  日期：2010.9

  Some triazolo-pyrazoline derivatives were synthesized to investigate their potential antidepressant activities. The chemical structures of the compounds were elucidated by IR, NMR and FAB(+)-MS spectral data and elemental analyses. Antidepressant-like activities of the test compounds (100 mg/kg) were screened using both modified forced swimming and tail suspension tests. Rota-Rod test was performed for the examination of probable neurological deficits due to the test compounds, which may interfere with the test results. The test compounds in the series exhibited different levels of antidepressant activities when compared to reference drug fluoxetine. None of the test compounds changed motor coordination of animals when assessed in the Rota-Rod test. Therefore, experimental results in this study were not interfered with motor abnormalities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and anticandidal activity of new triazolothiadiazine derivatives
  作者：Mehlika Dilek Altıntop、Zafer Asım Kaplancıklı、Gülhan Turan-Zitouni、Ahmet Özdemir、Gökalp İşcan、Gülşen Akalın、Şafak Ulusoylar Yıldırım

  DOI：10.1016/j.ejmech.2011.09.020

  日期：2011.11

  New triazolothiadiazine derivatives were synthesized via the ring closure reaction of 4-amino-5-substituted-2,4-dihydro-3H-1,2,4-triazol-3-thiones with phenacyl bromides. The compounds were tested in vitro against various Candida species and compared with ketoconazole. Among these compounds, the compound bearing cyclohexyl moiety and p-chlorophenyl substituent on triazolothiadiazine ring (2i) was found

  通过4-氨基-5-取代的2,4-二氢-3H-1,2,4-三唑-3-硫酮与苯甲酰基溴的闭环反应合成了新的三唑并二嗪衍生物。该化合物在体外针对各种念珠菌进行了测试，并与酮康唑进行了比较。在这些化合物中，发现在三唑并噻二嗪环（2i）上带有环己基部分和对氯苯基取代基的化合物是对抗白色念珠菌的最有效衍生物（ATCC 90028）。很显然，有抗念珠菌活性和两个官能部分，即脂环族基团和之间的正相关p三唑并噻二嗪环上的-氯苯基取代基。还使用MTT测定法研究了这些化合物的细胞毒性作用。化合物2a显示出最高的细胞毒性活性，而化合物2f显示出对NIH / 3T3细胞的最低细胞毒性活性。
• Synthesis of Some Novel Triazole Derivatives and Investigation of Their Antimicrobial Activities
  作者：Mehlika Dilek Altıntop、Zafer Asım Kaplancıklı、Gülhan Turan-Zitouni、Ahmet Özdemir、Fatih Demirci、Gökalp İşcan、Gilbert Revial

  DOI：10.1080/00397911.2010.501475

  日期：2011.8

  [image omitted] The aim of this study is to synthesize new triazole derivatives and investigate their antimicrobial activities. 4-Amino-5-(2-cyclohexylethyl)-3-[N-(benzothiazole-2-yl)acetamido]thio-4H-1,2,4-triazole and 4-amino-5-[2-(4-hydroxyphenyl)ethyl]-3-[N-(benzothiazole-2-yl)acetamido]thio-4H-1,2,4-triazole derivatives were prepared by the reaction of 2-chloro-N-(benzothiazole-2-yl)acetamides with 4-amino-5-(2-cyclohexylethyl)-2,4-dihydro-3H-1,2,4-triazol-3-thione and 4-amino-5-[2-(4-hydroxyphenyl)ethyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, respectively. The structures of these compounds were elucidated by infrared, 1H NMR, 13C NMR, mass spectra, and elemental analysis. The synthesized compounds were screened for their antimicrobial activities against various Candida species and pathogenic bacteria. Compound IIIg and compound IIIi were found to be the most potent derivatives against Candida species and tested bacteria, respectively.