N-methyl-2-(pyrazine-2-carbonyl)hydrazinecarbothioamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-methyl-2-(pyrazine-2-carbonyl)hydrazinecarbothioamide
• 英文别名: 1-Methyl-3-(pyrazine-2-carbonylamino)thiourea；1-methyl-3-(pyrazine-2-carbonylamino)thiourea
• 化学式: C₇H₉N₅OS
• 分子量: 211.247
• InChiKey: SFKDSMLUSFPLPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.94
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-methyl-2-(pyrazine-2-carbonyl)hydrazinecarbothioamide 在 sodium hydroxide 作用下， 反应 4.0h， 以93%的产率得到4-methyl-5-(pyrazin-2-yl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors

  摘要：

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.

  DOI：

  10.1007/s00044-014-1314-4
• 作为产物：
  描述：

  吡嗪甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 N-methyl-2-(pyrazine-2-carbonyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors

  摘要：

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.

  DOI：

  10.1007/s00044-014-1314-4

文献信息

• Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors
  作者：Reema Abu Khalaf、Ahmed Mutanabbi Abdula、Mohammad S. Mubarak、Mutasem O. Taha

  DOI：10.1007/s00044-014-1314-4

  日期：2015.6

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.