8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one | 1234370-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one
• 英文别名: 8-amino-6-[2-(4-methoxyphenyl)ethenyl]-3-sulfanylidene-2H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one
• CAS: 1234370-67-2
• 化学式: C₁₃H₁₂N₆O₂S
• 分子量: 316.343
• InChiKey: GEEICBVJCCSJGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 吡啶 作用下， 以61%的产率得到8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-7,8-dihydro-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,4-triazolo[4,3-b][1,2,4]triazin-7-one
  参考文献：
  名称：

  Glycosylation, Sugar Hydrazones, and Antimicrobial Evaluation of Some 6-Substituted-1,2,4-Triazines

  摘要：

  Hydrazinolysis of 4-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-3,4-dihydro-2H-[1,2,4] triazin-5-one (1) gave the corresponding hydrazino derivatives (2) Cyclocondensation of (2) with carbon disulfide furnished 8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one (3) which was treated with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (4) in pyridine to give the corresponding N-glucosyl derivative 5, which deblocked to give 8. Compound 2 was reacted with isatin 9 and/or isatoic anhydride 10 to afford 11 and 12. Treatment of 11 and 12 with (4) in pyridine gave the corresponding mono glucosyl derivatives 13 and 14, which were deblocked by ammonia and afforded 15 and 16. Condensation of 2 with aldoses afforded the corresponding cyclic products 17a-f and with D-fructose furnished 18. Acetylation of 17b, d afforded the corresponding polyacetyl derivatives 19b,d. Compound 2 condensed with some aromatic aldehydes in boiling methanol and gave 20a-f. The newly synthesized compounds were tested as antimicrobial agents.

  DOI：

  10.1080/15257770903454482
• 作为产物：
  描述：

  二硫化碳 、 4-amino-3-hydrazino-6-[2-(4-methoxyphenyl)vinyl]-4H-[1,2,4]triazin-5-one 在 吡啶 、 溶剂黄146 作用下， 反应 6.0h， 以72.8%的产率得到8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one
  参考文献：
  名称：

  Glycosylation, Sugar Hydrazones, and Antimicrobial Evaluation of Some 6-Substituted-1,2,4-Triazines

  摘要：

  Hydrazinolysis of 4-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-3,4-dihydro-2H-[1,2,4] triazin-5-one (1) gave the corresponding hydrazino derivatives (2) Cyclocondensation of (2) with carbon disulfide furnished 8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one (3) which was treated with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (4) in pyridine to give the corresponding N-glucosyl derivative 5, which deblocked to give 8. Compound 2 was reacted with isatin 9 and/or isatoic anhydride 10 to afford 11 and 12. Treatment of 11 and 12 with (4) in pyridine gave the corresponding mono glucosyl derivatives 13 and 14, which were deblocked by ammonia and afforded 15 and 16. Condensation of 2 with aldoses afforded the corresponding cyclic products 17a-f and with D-fructose furnished 18. Acetylation of 17b, d afforded the corresponding polyacetyl derivatives 19b,d. Compound 2 condensed with some aromatic aldehydes in boiling methanol and gave 20a-f. The newly synthesized compounds were tested as antimicrobial agents.

  DOI：

  10.1080/15257770903454482

文献信息

• Glycosylation, Sugar Hydrazones, and Antimicrobial Evaluation of Some 6-Substituted-1,2,4-Triazines
  作者：A. A. El-Barbary、Y. A. Hafiz、M. S. Abdel-Wahed

  DOI：10.1080/15257770903454482

  日期：2010.1

  Hydrazinolysis of 4-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-3,4-dihydro-2H-[1,2,4] triazin-5-one (1) gave the corresponding hydrazino derivatives (2) Cyclocondensation of (2) with carbon disulfide furnished 8-amino-6-[2-(4-methoxyphenyl)vinyl]-3-thioxo-2,8-dihydro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one (3) which was treated with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (4) in pyridine to give the corresponding N-glucosyl derivative 5, which deblocked to give 8. Compound 2 was reacted with isatin 9 and/or isatoic anhydride 10 to afford 11 and 12. Treatment of 11 and 12 with (4) in pyridine gave the corresponding mono glucosyl derivatives 13 and 14, which were deblocked by ammonia and afforded 15 and 16. Condensation of 2 with aldoses afforded the corresponding cyclic products 17a-f and with D-fructose furnished 18. Acetylation of 17b, d afforded the corresponding polyacetyl derivatives 19b,d. Compound 2 condensed with some aromatic aldehydes in boiling methanol and gave 20a-f. The newly synthesized compounds were tested as antimicrobial agents.