4-amino-6-β-(4-chlorophenyl)vinyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

• 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-amino-6-β-(4-chlorophenyl)vinyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
• 英文别名: 4-amino-6-[(E)-2-(4-chlorophenyl)ethenyl]-3-sulfanylidene-2H-1,2,4-triazin-5-one
• 化学式: C₁₁H₉ClN₄OS
• 分子量: 280.738
• InChiKey: ANWQBXFTRLYKAF-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-6-β-(4-chlorophenyl)vinyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 在 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-(trans-β-(4-chlorophenyl)vinyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
  参考文献：
  名称：

  Selective Synthesis and Reactions of 6-Substituted- 2-β-galactosyl-1,2,4-triazines of Potential Anticancer Activity

  摘要：

  Selective synthesis and reactions of different 6-substituted-2-beta-D-galactosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones using the developed amino or aryl protecting group strategy were investigated. Primary human anticancer screening of twelve selected compounds (in vitro) resulted in an active compound against both MCF7 (Breast) and SF-268(CNS) cell lines.

  DOI：

  10.1081/ncn-120018621
• 作为产物：
  描述：

  4-氯苯甲醛 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-amino-6-β-(4-chlorophenyl)vinyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
  参考文献：
  名称：

  Synthetic Approach for Novel Fluorine Substituted Thiadiazaphosphole Fused 1,2,4-Triazinopyridiazine Moieties as Bactericidal Agents

  摘要：

  4-amino-6-styryl-3-mercapto-1,2,4-triazin-5-one (2) 与亚磷酸三乙酯和/或磷酸三乙酯在干燥的苯中回流，然后与肼在温热的乙醇-哌啶中进行环化反应，最后与三氟乙酸酐在二噁烷中沸腾，合成了新颖的氟取代噻二唑膦融合 1,2,4-triazino 吡啶（7 和 8）。借助元素分析和光谱数据阐明了产物的结构。与标准抗生素氯霉素相比，所有目标化合物都对大肠杆菌具有杀菌作用。

  DOI：

  10.14233/ajchem.2016.19555

文献信息

• Synthesis, characterization and biological activity of some 1,2,4-triazine derivatives
  作者：A. A. El-Barbary、M. A. Sakran、A. M. El-Madani、Claus Nielsen

  DOI：10.1002/jhet.5570420528

  日期：2005.7

  4-Amino-6-methyl-3-(2H)-thioxo-5-(4H)-oxo-1,2,4-triazine (1) was condensed with 2-methyl (or phenyl)-4H-3,1-benzoxazin-4-one (5a,b) in boiling acetic acid to give compounds 8-11. Reacting 1 with chloroacetyl chloride afforded the corresponding chloroacetamido and triazinothiadiazine derivatives 12 and 13. Condensing 2 with succinic anhydride and/or phthalic anhydride yielded compounds 14 and 15. Benzoylation

  4-氨基-6-甲基-3-（2- ħ）-thioxo -5-（4- ħ） -氧代-1,2,4-三嗪（1）中的溶液用2-甲基（或苯基）-4-冷凝ħ -在沸腾的乙酸中的3，1-苯并恶嗪-4-酮（5a，b）得到化合物8-11。将1与氯乙酰氯反应，得到相应的氯乙酰胺基和三叠氮杂二嗪衍生物12和13。冷凝2与琥珀酸酐和/或邻苯二甲酸酐，得到化合物14和15。4-氨基-6-甲基-3-（2 H）-thioxo-5-（4 H）-oxo -2-（2,3,4,5- tetra- O的苯甲酰化-乙酰基-α-D-吡喃-葡萄糖基）-1,2,4-三嗪（19）得到相应的4- N，N-二苯甲酰基衍生物20。所述的去块Ñ -2糖苷21和小号糖苷22由甲醇氨，得到化合物23和24。4-氨基糖苷25a的乙酰化得到相应的4-单-和4-二乙酰基衍生物26和27。25a，b的脱氨基得到化合物28a，b。化合物28b的甲基化得到相应的N4-和S-甲基衍生物29和30。
• Selective Synthesis and Structure of 6-Arylvinyl-2- and 4-Glucosyl-1,2,4-triazines of Expected Interesting Biological Activity
  作者：Abdel Kader Mansour、Yehia A. Ibrahim、Nasser S. A. M. Khalil

  DOI：10.1080/07328319908044880

  日期：1999.10

  The 6-beta-arylvinyl-2- and 4-glucosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones were synthesized with high selectivity using the recently developed amino protecting group strategy. The structure of these new glucosides was established chemically, and spectroscopically. Also, some interesting chemical transformations and rearrangements were observed.
• BADAWY, MOHAMED, A.;ABDEL-HADY, SAYED, A. L.;EID, MOHGA, M.;IBRAHIM, YEHI+, CHEM. BER., 1984, 117, N 3, 1083-1088
  作者：BADAWY, MOHAMED, A.、ABDEL-HADY, SAYED, A. L.、EID, MOHGA, M.、IBRAHIM, YEHI+

  DOI：——

  日期：——
• Synthetic Approach for Novel Fluorine Substituted Thiadiazaphosphole Fused 1,2,4-Triazinopyridiazine Moieties as Bactericidal Agents
  作者：Mohammed Saleh Tawfek Makki、Reda Mohammady Abdel Rahman、Ola Ahmad Abu Ali

  DOI：10.14233/ajchem.2016.19555

  日期：——

  Novel fluorine substituted thiadiazaphosphole fused 1,2,4-triazino pyridiazines (7 and 8) were synthesized by refluxing of 4-amino-6-styryl-3-mercapto-1,2,4-triazin-5-one (2) with triethylphosphite and/or triethylphospate in dry ethyl benzene followed by cycloaddition with hydrazine in warm ethanol-piperidine and finally boil with trifluoroacetic anhydride in dioxane. Structure of the products was elucidated with the help of elemental analysis and spectral data. All the target compounds evaluated as bactericidal agents against Escherichia coli compared with chloromycetin as standard antibiotic.

  4-amino-6-styryl-3-mercapto-1,2,4-triazin-5-one (2) 与亚磷酸三乙酯和/或磷酸三乙酯在干燥的苯中回流，然后与肼在温热的乙醇-哌啶中进行环化反应，最后与三氟乙酸酐在二噁烷中沸腾，合成了新颖的氟取代噻二唑膦融合 1,2,4-triazino 吡啶（7 和 8）。借助元素分析和光谱数据阐明了产物的结构。与标准抗生素氯霉素相比，所有目标化合物都对大肠杆菌具有杀菌作用。
• Selective Synthesis and Reactions of 6-Substituted- 2-β-galactosyl-1,2,4-triazines of Potential Anticancer Activity
  作者：Abdel Kader Mansour、Mohga M. Eid、Nasser S. A. M. Khalil

  DOI：10.1081/ncn-120018621

  日期：2003.4

  Selective synthesis and reactions of different 6-substituted-2-beta-D-galactosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones using the developed amino or aryl protecting group strategy were investigated. Primary human anticancer screening of twelve selected compounds (in vitro) resulted in an active compound against both MCF7 (Breast) and SF-268(CNS) cell lines.