1,4-bis-(5-[hydrazinocarbonylmethylthio]-4-(m-tolyl)-1,2,4-triazol-3-yl)butane | 1266399-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-bis-(5-[hydrazinocarbonylmethylthio]-4-(m-tolyl)-1,2,4-triazol-3-yl)butane
• 英文别名: 2-[[5-[4-[5-(2-Hydrazinyl-2-oxoethyl)sulfanyl-4-(3-methylphenyl)-1,2,4-triazol-3-yl]butyl]-4-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide；2-[[5-[4-[5-(2-hydrazinyl-2-oxoethyl)sulfanyl-4-(3-methylphenyl)-1,2,4-triazol-3-yl]butyl]-4-(3-methylphenyl)-1,2,4-triazol-3-yl]sulfanyl]acetohydrazide
• CAS: 1266399-89-6
• 化学式: C₂₆H₃₂N₁₀O₂S₂
• 分子量: 580.738
• InChiKey: PUPXEVVKJXVPEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  222
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-吡啶甲醛 、 1,4-bis-(5-[hydrazinocarbonylmethylthio]-4-(m-tolyl)-1,2,4-triazol-3-yl)butane 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以55%的产率得到1,4-bis-(5-[N'-(pyridin-4-yl)methylenehydrazinocarbonylmethylthio]-4-(3-tolyl)- 1,2,4-triazol-3-yl)butane
  参考文献：
  名称：

  Synthesis and in vitro Cytotoxicity Studies of Certain Novel Heterocycles Derived from Bis 1, 2, 4-Triazoles and their DNA Damage Studies

  摘要：

  本研究描述了由 1，4-双（5-[肼基甲硫基]-4-苯基-1,2,4-三唑-3-基）丁烷（1a-b）衍生的一系列杂环化合物的合成和细胞毒性评估。三唑并三唑（9-15）和噻二唑（16-18）分别由各自的硫代氨基脲中间体（2-8）制备而成。希夫碱（19-24）是由（1a, b）在乙酸介质中与不同的羧醛反应制备而成。通过红外光谱、核磁共振和质谱研究对所有合成化合物进行了表征。采用标准的 MTT 法对三种人类癌症细胞系进行了体外细胞毒性潜力评估：肺癌 A-549、结肠癌 HT-29 和乳腺癌 MDA MB-231。碱性彗星试验评估了化合物 24 的 DNA 损伤活性。

  DOI：

  10.2174/1573406411309080008
• 作为产物：
  描述：

  4-(3-methylphenyl)-3-[4-[4-(3-methylphenyl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]butyl]-1H-1,2,4-triazole-5-thione 在 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 1,4-bis-(5-[hydrazinocarbonylmethylthio]-4-(m-tolyl)-1,2,4-triazol-3-yl)butane
  参考文献：
  名称：

  1,4-双[5-硫代-4-取代-1,2,4-三唑-3-Yl]-丁烷衍生的双-1,3,4-恶二唑和双-吡唑及其DNA的合成和细胞毒性结合研究

  摘要：

  新系列1,4-双[5-(5-mercapto-1,3,4-oxadiazol-2-yl-methyl)-thio-4-located-1,2,4-triazol-3-yl] -丁烷 7-12 和 1,4-双 [5- (1-oxo-1- (3,5 二甲基吡唑-1-基) -甲基) -硫代-4-取代的-1,2,4-三唑- 3-基]-丁烷13-18由1,4-双（5[肼基羰基甲硫基]-4-取代-1,2,4-三唑-3-基）丁烷衍生物合成1-6。所有合成的化合物均通过红外、核磁共振和质谱研究进行表征。使用标准 MTT（3-（4,5-二甲基噻唑-2-基）-2,5-溴化二苯基四唑鎓）针对一组三种人类癌细胞系筛选合成的化合物 7-18 的体外细胞毒性潜力：肺癌 A-549、结肠癌 HT-29 和乳腺癌 MDA MB-231。通过吸收滴定法对三种有效分子进行了 DNA 结合研究。

  DOI：

  10.1002/ardp.201000177

文献信息

• Synthesis, in vitro cytotoxicity, and anti-microbial studies of 1,4-bis(4-substituted-5-mercapto-1,2,4-triazol-3-yl)butanes
  作者：Madhusudan Purohit、Yergeri C. Mayur

  DOI：10.1007/s00044-010-9517-9

  日期：2012.2

  Synthesis and evaluation of cytotoxicity and anti-microbial activity of a series of 1,4-bis(4-substituted-5-mercapto-1,2,4-triazol-3-yl)butane derivatives comprising thioether functionality and other pharmacophore modifications are described. All the newly synthesized compounds were characterized by IR, NMR, elemental analyses, and mass spectral studies. The compounds 4a-f, 5a-f, and 6a-f were evaluated for in vitro cytotoxicity potential using the standard MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against a panel of three human cancer cell lines: Lung carcinoma A-549, Colon carcinoma HT-29, and Breast Cancer MDA MB-231. All the compounds were subjected to in vitro anti-bacterial activity against Bacillus subtilus (ATCC 6633), Staphylococcus aureus (ATCC-25923), Escherichia coli (ATCC-25922), and Pseudomonas aeruginosa (ATCC-27853) and their minimal inhibitory concentrations were determined.
• Synthesis and Cytotoxicity of Bis-1,3,4-oxadiazoles and Bis-pyrazoles Derived from 1,4-Bis[5-thio-4-substituted-1,2,4-triazol-3-Yl]-butane and Their DNA Binding Studies
  作者：Madhusudan Purohit、V.V.S. Rajendra Prasad、Yergeri C. Mayur

  DOI：10.1002/ardp.201000177

  日期：2011.4

  substitued‐1,2,4‐triazol‐3‐yl]‐butane 13‐18 were prepared from 1,4‐bis(5[hydrazinocarbonylmethylthio]‐4‐substituted‐1,2,4‐triazol‐3‐yl) butane based derivativess were synthesized 1‐6. All the synthesized compounds were characterized by IR, NMR and Mass spectral studies. The synthesized compounds 7‐18 were screened for in‐vitro cytotoxicity potential using the standard MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2

  新系列1,4-双[5-(5-mercapto-1,3,4-oxadiazol-2-yl-methyl)-thio-4-located-1,2,4-triazol-3-yl] -丁烷 7-12 和 1,4-双 [5- (1-oxo-1- (3,5 二甲基吡唑-1-基) -甲基) -硫代-4-取代的-1,2,4-三唑- 3-基]-丁烷13-18由1,4-双（5[肼基羰基甲硫基]-4-取代-1,2,4-三唑-3-基）丁烷衍生物合成1-6。所有合成的化合物均通过红外、核磁共振和质谱研究进行表征。使用标准 MTT（3-（4,5-二甲基噻唑-2-基）-2,5-溴化二苯基四唑鎓）针对一组三种人类癌细胞系筛选合成的化合物 7-18 的体外细胞毒性潜力：肺癌 A-549、结肠癌 HT-29 和乳腺癌 MDA MB-231。通过吸收滴定法对三种有效分子进行了 DNA 结合研究。
• Synthesis and in vitro Cytotoxicity Studies of Certain Novel Heterocycles Derived from Bis 1, 2, 4-Triazoles and their DNA Damage Studies
  作者：Madhusudan Purohit、Chandrashekhar Mangannavar、Mayur Yergeri

  DOI：10.2174/1573406411309080008

  日期：2013.10.1

  Synthesis and evaluation of cytotoxicity of a series of heterocyclic compounds derived from 1, 4-bis-(5- [hydrazinocarbonylmethylthio]-4-phenyl-1,2,4-triazol-3-yl) butane (1a-b) are described. The triazolo-triazoles (9-15) and thiadiazoles (16-18) were prepared from respective thiosemicarbazide intermediates (2-8). The Schiff bases (19-24) were prepared from (1a, b) by reacting with different carboxaldehydes in acetic acid medium. All the synthesized compounds were characterized by IR, NMR and Mass spectral studies. The compounds were evaluated for in vitro cytotoxicity potential using the standard MTT assay against a panel of three human cancer cell lines: Lung carcinoma A-549, Colon carcinoma HT-29 and Breast Cancer MDA MB-231. The DNA damage activity of the compound 24 was evaluated by alkaline comet assay.

  本研究描述了由 1，4-双（5-[肼基甲硫基]-4-苯基-1,2,4-三唑-3-基）丁烷（1a-b）衍生的一系列杂环化合物的合成和细胞毒性评估。三唑并三唑（9-15）和噻二唑（16-18）分别由各自的硫代氨基脲中间体（2-8）制备而成。希夫碱（19-24）是由（1a, b）在乙酸介质中与不同的羧醛反应制备而成。通过红外光谱、核磁共振和质谱研究对所有合成化合物进行了表征。采用标准的 MTT 法对三种人类癌症细胞系进行了体外细胞毒性潜力评估：肺癌 A-549、结肠癌 HT-29 和乳腺癌 MDA MB-231。碱性彗星试验评估了化合物 24 的 DNA 损伤活性。